Besides having a wonderful British accent, which Craig loved, David Wilkins is the Founder of SDR Leaders of EMEA and the Co-Founder of SDR Leaders of USA and APAC. David joins Co-Hosts Craig Rosenberg and Matt Amundson to dig into how sales leaders are overcoming the major issues facing SDRs (Sales Development Reps) in B2B sales today. David shares how successful sales leaders are implementing AI tools to cut down on excess admin work for their SDRs, why sales channels like cold-calling & video messages are outperforming email outreach, and how dialing up the difficulty of the sales training for your reps can keep them cool as can be on even their most cantankerous sales calls.

Plus, David outlines the totally standard, run-of-the-mill journey of how he went from studying at the second-worst university in the UK to working for the number-one mayonnaise manufacturer in the Netherlands and ended up getting into B2B sales. 

Also, Craig references a late-80s rap duo, Matt alludes to the promise of a brisket, and Producer Sam somehow manages to ask a decent salestech question after breaking the 4th wall earlier in the episode.

Critical Takeaways

• Excessive admin work is still eating the SDR role alive. In a surprising number of B2B companies, SDRs are still burning three-plus hours a day on manual admin tasks. That is not harmless busywork in B2B sales; it is precious selling time being quietly set on fire. Rather than replacing a human SDR with an AI avatar, target this admin & sales prep work for elimination with AI. 
• Email-first outbound has run out of runway. Email still has a place, but it should be just one piece of a larger outbound strategy that focuses more heavily on better-performing tactics like cold calls and social media touchpoints. The practical implication for sales and marketing leaders is simple: email can support the motion, but it cannot be the whole motion anymore.
• Sending videos and voice notes through LinkedIn messages works because they do something most outreach still does not: they make it obvious a real, honest-to-goodness human being is on the other end. That is especially useful in B2B SaaS, where copy-paste messages have saturated email, text, and even DM inboxes, and being able to interrupt that pattern buys sellers the few seconds of attention they need to make inroads.
• The sales training you provide for your SDRs and AEs should be significantly harder than anything they might deal with on a standard sales call. That way, if they find themselves in a delicate situation, they have the skills to stay calm and continue moving the conversation forward. A great way to give your sales reps more, well, reps is to use a training tool with AI-avatars of different customer profiles in sales scenarios.

Chapters

00:00 - Episode Preview

00:51 - Trans-Atlantic Holiday Customs and Re-Ranking of Meats 

04:11 - Introducing David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert

06:55 - David's Journey From a Terrible School to Amazing Mayo & Eventually a B2B Sales Job

15:10 - Why SDR Leaders Don't See Headcount as The Solution for Success with Sales Development in B2B SaaS 

30:18 - Why Cold-calling Beats Email for Engaging with Prospects

34:59 - Video Messages & Voice Notes Break the Pattern of B2B Sales Outreach

46:09 - Improving Sales Training with AI Avatars To Help SDRs Perform Better on Sales Calls

49: 57 - Predicting the Future Evolution of the SDR Role in B2B Sales & GTM

55:04 - Random Rap & Wrestling References Before Wrapping Up

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Epic Quotes

• “ Make the training harder than the game.” - David Wilkins
• “ Making this function what it is, which is a critical part of the revenue generating organization.” - David Wilkins
• “ I'm gonna be calling myself Ron now, if ever I get in trouble” - Ron Davidson

Connect with David

• LinkedIn: https://www.linkedin.com/in/daveewilkins/ 
• SDR Leaders of EMEA Website: https://sdr-leader.com/ 

Shoutouts

• Lars Nilsson: https://www.linkedin.com/in/lanilsson/ 
• Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales?utm_campaign=post-expanded-share&utm_medium=web 
• Travis Henry: https://www.linkedin.com/in/travisjhenry/ 
• Russell Hearl: https://www.linkedin.com/in/russhearl/ 
• PG.ai
• TitanX
• Nooks
• Hiya 
• Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ 
• Quibbly
• Synthesia
• Tavus
• Hyperbound
• Scott Albro
• Rodney-O & Joe Cooley: https://youtu.be/BynWb6swQ74?si=_7ykfGXyz0GDACRl 

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Kacie joins co-hosts Craig Rosenberg and Matt Amundson to unpack what B2B brands need to learn from B2C companies in order to build bold, unforgettable brands that increase revenue and redefine markets. 

Plus, Kacie outlines why B2B startups need to see building a founder brand as a pipeline engine, how to move beyond broken marketing attribution systems, and why brand marketing is making a massive comeback.

Also, Kacie shares the outcome of all her speakers getting food poisoning before an event, Craig explains why he’s bringing his son to Vegas, and Matt states his stance on the existence of ghosts. 

Critical Takeaways

• Founder-led brand and content works because buyers want conviction from the people shaping the company, not just polished messaging from the brand account. 
• The key to building a strong founder brand is finding the intersection of three things: 1. What is the founder an expert at? 2. What makes the founder utterly unique? 3. What does the target audience want and need?
• A bold brand doesn't mean punching competitors; it means being so weird, human, and mission-driven that people can't stop thinking about you. At Fastly, this meant leaning into engineer culture with quirky campaigns (literal messenger pigeons), bright red branding mirroring the founder's personality, and taking public stands on internet ethics. Find what makes your company authentically different and lean all the way into it.
• Your founder is the person with the most conviction on your team, and that conviction is what cuts through noise in crowded categories. Marketing should treat building and amplifying the founder's narrative as a top priority, not a side project. Invest time sitting with the founder to uncover what they stand for, what they hate, and what future they're building — then help them show up consistently.
• Sales leaders should map executive posts, thought leadership clips, and campaign creative to relevant strategic accounts, then use that content to multi-thread and re-engage deals. When a founder or visible executive has market credibility, reps get warmer entry points and stronger follow-up moments.
• Values only count when customers can feel them. If the brand story stops at messaging, buyers will eventually spot the gap. For example, Fastly’s brand worked because their stance showed up in customer selection, customer success, and even how they defined who they wanted to win with in the market.

Chapters

00:00 - Episode Preview

00:51 - Spooky Baseball

02:20 - Introducing Kacie Jenkins, Head of Marketing for Claude Code at Anthropic

05:46 -  Accidentally Hosting a Spooky Customer Advisory Board Retreat

12:53 - What Happens When All Your event Speakers get Food Poisoning

19:03 -  How Founders Can Seize the Story of Their Category and Own The Narrative

35:48 - How to Build Bold Brands for B2B SaaS

41:22 - Why brand fails without founder buy-in

47:23 - Marketing Attribution is Broken. Now what?

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Epic Quotes

• “The key to winning is real, true, authentic differentiation.” - Kacie Jenkins

Connect with Kacie

• LinkedIn: https://www.linkedin.com/in/kaciejenkins/ 
• Anthropic Website: https://www.anthropic.com/ 
• Claude Code Website: https://claude.com/product/claude-code 

Shoutouts

• Ruby James: https://www.linkedin.com/in/rubyjameslinkedin/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Artur Bergman: https://www.linkedin.com/in/crucially/ 
•  Katie Penner: https://www.linkedin.com/in/kathrynpenner/ 
• Kris Rudeegraap: https://www.linkedin.com/in/rudeegraap/ 

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Plus, Udi unpacks the three critical marketing leadership lessons he learned the hard way when a mistake in an email marketing campaign almost spiraled into a massive issue for one of the premier B2B SaaS brands in Silicon Valley today.   

Also, Craig admits to claims he confused someone on a call, Matt waxes poetic about a B2B SaaS company he doesn’t work for, and Producer Sam revels in an ever-elusive mention of the show notes. 

Critical Takeaways

• When a marketing mistake goes public, marketing leaders need to act decisively within hours, not days, and own it personally. A swift action paired with a personal response can de-escalate most complicated situations and help to quell even irate customers. By quickly taking personal accountability for the issue, you can turn a brand crisis into a trust-building moment.
• Teams should treat complaints as a signal, not the sample size. If a dozen people took the time to complain, many more probably felt the same way and stayed quiet. That is a strong operating principle for brand, product, and customer comms teams: they should respond to the unseen audience, not just the visible inbox.
• A key to building Gong’s human-feeling brand was deliberately connecting "trusted thought leader" with "relaxed, friendly person who wants to help you out" during an early brand workshop. Most B2B brands default to authoritative-plus-stuffy; product marketers and brand teams should explicitly codify an approachable, human counterweight in their brand guidelines.
• Use AI suggestions to find and filter out the obvious crap that everyone else would do in their marketing strategy. LLMs are a synthesis of (pretty much) everything on the internet, which means they’re great at telling you about what’s already out there. The next time you’re coming up with ideas for a marketing campaign, ask your LLM of choice for its recommendations and use those as a guide for what not to do.
• Rather than going fully with either gated or ungated content, using them in tandem can increase visibility and conversions. When sharing ungated content publicly, link to relevant gated assets and resources from within the ungated piece of content. This way, you get the visibility benefits of ungated content while getting your gated assets in front of a larger target audience.

Chapters

00:00 - Episode Preview

00:56 - Craig Flounders While Filibustering to Find an Excuse For His Profile Photo Fiasco

03:16 - Introducing Udi Ledergor, Chief Evangelist at Gong

05:46 - 3 Critical Marketing Lessons Learned from an Email Campaign that Almost Ruined a Massive B2B SaaS Brand

17:02 - How Gong Intentionally Built an Authentic, Sincere, & Human Brand for A B2B SaaS Startup

22:06 - Reimagining B2B Marketing Events To Optimize for Guest Experience

28:48 - Using AI as a Quality Filter for Marketing Ideas

33:36 - The Two Ways to Use AI in Your Work

35:19 - Where Gong Lands in the Gated-versus-Ungated Content Debate

45:26 - The Basics of Email Marketing That Still Work in B2B

47:45 - The Bait & Switch Twitter Play for Boosting Web Traffic For Startups

51:31 - How Gong Develops its Content Marketing and Distribution Strategy Together

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Epic Quotes

• “We're sometimes over-reliant on all this automation crap. We like that it saves our team work, but we don't realize what we're giving up in return.” - Udi Ledergor
• “The worst thing that can happen to you is not that some people hate what you're doing. The worst thing that can happen to you is indifference.” -  Udi Ledergor

Connect with Udi

• LinkedIn: https://www.linkedin.com/in/udiledergor/ 
• Gong’s Website: https://www.gong.io/ 
• Udi’s Book: https://a.co/d/0Cix9Ll 
• Udi’s Website: https://www.udiledergor.com/ 

Shoutouts

• Ruby James: https://www.linkedin.com/in/rubyjameslinkedin/ 
• Chris Orlob: https://www.linkedin.com/in/chrisorlob/ 
• Chris’ Episode: https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: https://open.substack.com/pub/thetransaction/p/rebuilding-b2b-customers-confidence
• Kyle Lacy: https://www.linkedin.com/in/kylelacy/ 
• Top Swear Words - Gong: https://www.gong.io/blog/how-cursing-impacts-sales 
• Alec Paul: https://www.linkedin.com/in/alecjpaul/ 
• Alec’s Episode: https://open.substack.com/pub/thetransaction/p/becoming-a-linkedin-master-with-alec 
• Danny Hutto: https://www.linkedin.com/in/dannyhutto/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Stacey Epstein is the CEO of Structured, the only AI-native channel marketing platform purpose-built for complex partner ecosystems. She is also the Host of AI’ve Got Questions, a casual, candid podcast for marketers trying to make sense of the fast-moving world of AI. Stacey joins co-hosts Matt Amundson and Craig Rosenberg to discuss why your positioning framework needs to be at the core of every marketing campaign, how hiring for taste drives differentiation, and how to inject the voice of your customers into your brand.

Plus, Stacey shares how to maximize the impact of your CEO or Founder throughout your marketing.

Also, Craig talks about the miracle of birth, Matt mixes up the abbreviations of an African country, and Producer Sam expounds on the etymology of the word “czar”. 

Critical Takeaways

• Before you start executing any marketing tactics, you need to develop a strong positioning framework that clearly articulates what your company does, why it matters, who the buyer is, and what makes you different. Way too many B2B companies are still doing "random acts of marketing" where every campaign differs from the website messaging, creating inconsistent brand experiences that confuse buyers and dilute impact.
• As AI handles more aspects of content creation, campaign distribution, and administrative tasks, marketing teams should prioritize hiring "tastemakers" who demonstrate exceptional judgment in evaluating strategic creative decisions. The ability to curate, refine, and elevate work, whether human-made or AI-generated, matters more than the ability to execute tactical tasks manually.
• Treat your S-1 as the foundation for all Go-To-Market activities. It should be the basis of your positioning, informing everything from why you exist, what your product does, points of competitive differentiation, and your future vision
• Organizations need a centralized AI leader, whether in marketing ops, revenue ops, or IT, to coordinate AI initiatives across functions and prevent teams from burying themselves in disjointed AI projects. This role ensures strategic alignment, prevents redundant tool purchases, and helps teams focus AI adoption on high-impact use cases rather than experimenting randomly.

Chapters

00:00 - Episode Preview

00:42 - Craig’s Story of Endings and New Beginnings

02:46 - Introducing Stacey Epstein, CEO of Structured

07:16 - Accidentally Sending an Embarrassing Email to Every Co-worker in an Entire Region

15:34 - Why Positioning is Foundational to Your Brand and Storytelling

21:29 -  How to Get Better Input on Marketing from Founders & CEOs

31:58 - What Stacey's Learned about AI From Hosting her Podcast

34:54 - Why You Need to Hire “Taste Makers” in an AI-first world

41:50 - A Brief Aside on the Etymology of Czar/Tsar

43:35 - Why Companies are Hiring GTM Engineers & The Impact They're Having

45:58 - How to Lead AI Implementation in Your Company

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “ Who owns AI in the company?” - Stacey Epstein
• “ I love coming back to use cases, because use cases come back to the benefit for the company. So instead of telling me what the product does, tell me how that would be used.” - Stacey Epstein

Connect with Stacey

• LinkedIn: https://www.linkedin.com/in/staceyepstein/ 
• Magnetic GTM Website: https://www.magneticgtm.com/ 
• Podcast: https://aivegotquestions.buzzsprout.com/ 
• Structured Website: https://structured.ai/ 

Shoutouts

• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• David’s Episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-market
• Lisa Cole: https://www.linkedin.com/in/lisacole01/ 

James Kaikis is the Founder of GTMshift, Co-Founder of SolutionExec, Co-Founder of AI Sales Studio, and Host of The GTMshift Interview Series. James joins Matt Amundson and Craig Rosenberg to unpack the evolving role of sales reps, how to use the GTM Innovator’s Framework to stay up on AI advances, and why B2B SaaS companies must refocus their GTM motions on their customers.

Plus, James shares his top spots to eat in Chicago.

Also, Craig calls Matt a technical buyer, Matt rates Craig’s follicular health, and Producer Sam forgets how math works. 

Critical Takeaways

• Technical buyers have done extensive research before ever talking to you and know their problems better than you do. Stop running rigid qualification frameworks like BANT or MEDDIC that waste their time asking questions they've already answered internally. Instead, get straight to demonstrating how your solution solves their specific problem with their actual data, positioning yourself as a consultant helping them buy rather than a salesperson trying to extract information.
• Sales reps must be able to demonstrate the product themselves for lower-complexity solutions, especially when selling to other sales or marketing professionals. If you're selling sales technology but can't give a demo because "that's what SEs do," you've already lost credibility with your buyer. Invest time learning your product deeply enough to have hands-on conversations, or accept that AI-proficient competitors will replace you.
• Shift your focus from new logos to customer expansion. B2B SaaS companies are now generating more net new revenue from existing customers than new logo acquisition for the first time. Every customer you close should have a clear expansion roadmap within the first 90 days, with multiple upsell opportunities identified before implementation completes.
• Vertical SaaS represents one of the few remaining competitive moats as horizontal solutions get commoditized overnight by AI. Sales reps must develop deep expertise in specific industries—understanding regulatory requirements, workflow nuances, and sector-specific language that generic reps cannot replicate. For example, if you're selling into pharmaceutical, financial services, or manufacturing, you need to speak their language authentically or technical buyers will immediately dismiss you as lacking credibility.
• The traditional AE role that handled prospecting, discovery, demoing, forecasting, product knowledge, and closing is fundamentally broken because it asks too much of one person. Your role must narrow to being a customer-centric problem solver who builds trust and delivers value, while AI handles pipeline generation and SEs handle technical depth. Sales professionals who cannot adapt to this narrower, more specialized role will be replaced by solutions engineers who understand the product deeply and can build trust through hands-on demonstrations rather than sales techniques.

Chapters
00:00 - Episode Preview
00:50 - Checking in on Craig’s Follicular Growth, Grooming & Glasses
03:12 - Introducing James Kaikis, Founder of GTMshift
09:06 - The Life-changing Impact AI Innovation Had on James
23:17 - B2B SaaS has Forgotten about the Customer & Their Experience
31:18 -  The Changing Role of Sales Reps & Why Your Next Account Exec Should be a Solutions Engineer
41:02 - How the Next Generation of Sales Reps will be Trained & Interact with AI
50:11 - The Opportunity for Experiential Selling that AI Makes Feasible
59:04 - Quick Review of the Chicago Cuisine Scene

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Epic Quotes

• “We have lost sight in B2B SaaS of who matters.” - James Kaikis
• “Trust and value are the ultimate currency and this next wave of B2B SaaS.” - James Kaikis

Connect with James

• LinkedIn: https://www.linkedin.com/in/jameskaikis/ 
• GTMShift Website: https://gtmshift.com/ 
• AI Sales Studio Website: 
• SolutionExec Website: https://solutionexec.com/ 
• The GTM Shift Interview Series: https://gtmshift.com/the-gtmshift 
• Linktree: https://linktr.ee/jkaikis 

Shoutouts

• Doug Landis: https://www.linkedin.com/in/douglandis/ 
• Doug’s Episode: https://open.substack.com/pub/thetransaction/p/overcoming-outbound-challenges-with 
• Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ 
• Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ 
• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• David’s Episode: https://thetransaction.substack.com/p/building-an-ai-first-go-to-market 
• MIT Study on AI Adoption: https://mitsloan.mit.edu/ideas-made-to-matter/productivity-paradox-ai-adoption-manufacturing-firms 
• Craig’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/everything-s-back-on-the-table-why-ai-is-revolutionizing-gtm-with-craig-rosenberg 
• Jeff Margolese’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/the-solution-exec-guide-to-navigating-the-great-ai-shift-with-jeff-margolese 
• Dave Brock: https://www.linkedin.com/in/davebrock/ 
• Dave’s Episode: https://open.substack.com/pub/thetransaction/p/really-knowing-your-customer-with?utm_campaign=post-expanded-share&utm_medium=web 
• Trivoli Tavern: https://www.trivolitavern.com/trivoli 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Omar Akhtar is the Founder and Principal Analyst of Benchmarker and the Director of Content at UserTesting. Omar joins co-hosts Matt Amundson & Craig Rosenberg to dive into the B2B marketing data from Benchmarker’s latest survey, why the most successful companies are spending more on brand than demand, and how events have emerged as one of the top growth channels in go-to-market.

Plus, Omar digs into when to prioritize paid versus organic channels in your marketing mix.

Also, Craig outlines the plans for his kid’s booze-fueled birthday party, Matt laughs at an inopportune moment, and Producer Sam says ‘raccoon’. 

Critical Takeaways

• Doing more with less is dead. You can’t cut your way to growth. Marketing leaders need to choose between efficient growth or exponential growth and spend accordingly. 
• The companies that are actually hitting or exceeding their targets are spending at least the same, if not more, on brand as they are on demand. The companies that are performing the worst are overspending on demand over brand marketing.
• When new account growth is the priority, marketing teams should lean into paid search and paid social even though they’re expensive, because these paid channels can deliver faster growth and can outperform organic channels for reach.
• Dinners and small events can be great, but you can easily ruin them by being overly pushy and sales-y. If someone is talking product before anyone’s had a drink, you need to nip that in the bud. Also, some consultants can be pitchy, so invite them selectively.
• SaaS marketers are great at deploying amazing new tactics; however, on the whole, they lack a strong foundation in the marketing basics. Before you learn about the next bleeding-edge tool, take a minute to brush up on the building blocks, like positioning, targeting, and messaging.

Chapters

00:00 - Episode Preview

01:23 - Introducing Omar Akhtar, The Founder of Benchmarker

03:54 - A Perilously Precipitous Sales Call

06:01 - How Omar Moved From Rockstar to B2B Marketing Analyst

12:26 - Craig’s Dog Crashes the Party in Multiple Ways

13:32 - What Benchmarker’s Data has Revealed about Successful B2B Marketing Teams

21:26 - Why the Best Marketing Teams are Spending More on Brand Marketing

23:56 - Where Content Marketing Fits in the Modern B2B Marketing Mix

30:34 - Events & Small Dinners are Converting Like Crazy, but Please Don’t Overdo Them

37:24 - No Amount of Great Marketing Can Overcome a Crap Product, Have a Good Product & Execute the Basics of Marketing Well

44:11 - What Makes Clay’s Marketing So Special

50:21 - How Gong Survived the Latest SalesTech Revolution & is Now Thriving

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Epic Quotes

• “ This idea that we used to have for a long time, where you have to do more with less doesn't hold true anymore, because you can't cut your way to growth anymore.” - Omar Akhtar
• “We’re really in a B2B SaaS recession.” - Omar Akhtar

Connect with Omar

• LinkedIn: https://www.linkedin.com/in/omarbilalakhtar/ 
• Benchmarker Website: https://www.benchmarkerdata.com/ 
• UserTesting Website: https://www.usertesting.com/ 

Shoutouts

• Amy Holtzman: https://www.linkedin.com/in/aholtzman/ 
• Amy’s Episode: https://open.substack.com/pub/thetransaction/p/crafting-an-exceptional-event-marketing?r=3iae7z&utm_campaign=post&utm_medium=web 
• Udi Ledergor: https://www.linkedin.com/in/udiledergor/ 
• Chris Orlob: https://www.linkedin.com/in/chrisorlob/ 
• Chris’s Episode:  https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis?utm_campaign=post-expanded-share&utm_medium=web 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in?utm_campaign=post-expanded-share&utm_medium=web 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Kathy joins co-hosts Craig Rosenberg & Matt Amundson to discuss where so many go-to-market leaders go wrong with their segmentation, why your message matters more than the channel you deliver it through, and how to design a successful mid-market marketing org amidst massive pressure for budget cuts.

Also, Craig bemoans eating vegetables, Matt gives an update on Craig’s health, and some may have been kidnapped at Producer Sam’s house. 

Critical Takeaways

• Before chasing hyper-specifc and fancy AI tools, codify ICP, targeting, messaging, and what “good” outreach looks like. Then use AI to scale research and execution (with humans judging output), instead of hoping automation will invent strategy from scratch.
• If the account list is wrong, everything downstream gets harder (sales cycle, conversion, retention, even CSM load). Institutionalize segmentation by use case and continuously prune/refresh the target universe instead of debating tactics in the abstract.
• Stop obsessing over which channels you’re using and start focusing more on whether you have something worth saying to a specific buyer group. Then should ship that personalized, relevant message across every relevant channel as an integrated system, not as disconnected one-off campaigns.

Chapters

00:00 Harrowing Health Foods, Rave Recaps, & Tennis Talk
08:30 Introducing Kathy Macchi, Co-founder at Inverta

12:40 The Business Concerns Coming up In CMO Councils, Primarily AI & Budget Cuts

18:43 Why Cultivating Good Taste Transcends AI Advancements & Solving The Problem Before Adding AI Tools

30:27 AI's Impact on B2B Marketing Jobs and Economy

32:37 Rethinking Marketing and Business Processes with AI

34:06 The Role of Effective Targeting for Account-Based Marketing in the AI-era

37:02 Effective Use of AI in Marketing

42:13 Messaging + B2B Marketing Channel Strategies and Multi-Channel Marketing

53:04 B2B Sales and Territory Planning

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Epic Quotes

• “The who is everything” - Kathy Macchi
• “ We forgot that early pipeline, until you figure it out, costs money.  It costs money and you're going to fail.” - Craig Rosenberg

Connect with Kathy

• LinkedIn: https://www.linkedin.com/in/kathy-macchi-aa148b/ 
• Inverta Website: https://www.inverta.com/ 

Shoutouts

• Geoffrey Moore: https://www.linkedin.com/in/geoffreyamoore/ 
• Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ 
• Carlos Alcaraz
• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• Our Episode with David: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-market
• Omar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Joining the show are the Metrics Brothers, Ray Rike and Dave Kellogg! Ray is the Founder & Chief Evangelism Officer of Benchmarkit, Host of Metrics That Measure Up, a Founding Member of the SaaS Metrics Standards Board, and is an LP at Stage 2 Capital.

Dave co-hosts The Metrics Brothers Podcast, writes the incomparable ‘Kellblog’, and is an EIR at Balderton Capital.

Dave and Ray join co-hosts Matt Amundson and Craig Rosenberg to discuss the importance of brand investment in the AI age, overcoming the pipeline generation crisis in B2B SaaS, and how GTM leaders can drain the “metrics swamp.”

Plus, Dave divulges which SaaS metrics he finds loathsome and Ray shares his unique method for calculating Marketing CAC.

Also, Craig airs an ambrosia-related grievance, Matt unveils an old school tactic he’s still using, and Producer Sam falsely announces an exclusive scoop on The Transaction. 

Critical Takeaways

• Treat answer engine optimization (AEO) as a real channel, not a buzzword. As answer engines and generative AI search tools aggregate from dozens of sources but surface only a few. Meaning that you either show up in the top 2-3 responses or you effectively disappear. Teams should build use-case-level content, distribute it widely, and make it novel enough that answer engines want to quote it, while also building their own audience (newsletter, podcast, communities) so they’re not fully dependent on Google’s (or ChatGPT’s) algorithm.
• Inbound hand-raisers are a much better primary brand KPI than ‘share of voice’ measurements. Watch what percent of qualified pipeline and new ARR comes from inbound hand-raisers. GTM leaders should explicitly target a higher share of pipeline from inbound, track its close rates and ACVs versus outbound, and use that to justify continued brand and content investment.
• Focus more on the number of opportunities and cost per opportunity, not just total pipe. Revenue teams should watch both volume and dollars by source, so they can see, for example, whether brand-driven inbound is generating fewer but much better-quality opportunities and adjust their mix and SLAs accordingly.
• If you want overall efficiency, use Marketing CAC (sales + marketing over new ARR); if you want to compare programs, use pipeline generated divided by demand-gen program spend only. GTM leaders should keep CAC reserved for the full go-to-market machine, then use pipe-to-spend for campaign and channel decisions, excluding fixed headcount so they understand the ROI of the next incremental dollar.
• Sales and marketing leaders must acknowledge the current “pipeline crisis” in B2B SaaS, characterized by insufficient pipeline coverage and declining efficiency. Teams should track both the volume and cost of pipeline generated, and forecast pipeline coverage across all sources (marketing, SDRs, alliances, PLG, etc.) early and often.
• Aligning on metrics is a long-term, iterative process that requires persistence and cross-functional buy-in. 

Chapters

00:00 Episode Preview

01:48 Introducing Ray Rike and Dave Kellogg, The Metrics Brothers

05:40 How GTM Leaders can Escape from their ‘Dashboard Hell’

11:08 Which Metrics Matter to Your Board

18:37 Overcoming The B2B SaaS Pipeline Crisis

24:38 The Difference Between Search Engine Optimization & Answer Engine Optimization

29:52 Why Brand Still Matters in the age of AI & How to Measure Brand

45:21 Why B2B Marketers Need to Measure both Opportunity Count & Cost Per Opportunity

47:38 Why Pipeline Coverage Ratio is so Critical for B2B SaaS Startups

51:21 Examining Tantalus & The Cultural Impact of Ambrosia in All of Its Forms

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Epic Quotes

• “The faster growing companies actually are spending more on brand than on demand.” - Ray Rike
• “ My least favorite SaaS metric? Rolling four-quarter pipeline.” - Dave Kellogg
• “ Branding is marketing without a call to action.” - Dave Kellogg

Connect with Ray & Dave

• Ray’s LinkedIn: https://www.linkedin.com/in/rayrike/ 
• Dave’s LinkedIn: https://www.linkedin.com/in/kelloggdave/ 
• The Metrics Brother Podcast: https://podcasts.apple.com/us/podcast/the-metrics-brothers-fka-saas-talk/id1687214133 
• Metrics that Measure Up Podcast: https://podcasts.apple.com/us/podcast/metrics-that-measure-up/id1525571613 
• Benchmarkit Website: https://www.benchmarkit.ai/ 
• Dave’s Blog: https://kellblog.com/ 
• Balderton Capital: https://www.balderton.com/ 

Shoutouts

• Ray’s first Episode on The Transaction: https://open.substack.com/pub/thetransaction/p/harnessing-the-magic-of-metrics-with 
• Avinash Kaushik: https://www.linkedin.com/in/akaushik/ 
• Avinash’s Newsletter: https://www.kaushik.net/avinash/marketing-analytics-intersect-newsletter/ 
• Avinash’s SEO vs AEO article: https://www.kaushik.net/avinash/ai-age-marketing-bye-seo-hello-aeo/ 
• Omar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/ 
• Benchmarker: https://www.benchmarkerdata.com/ 
• Exit Five: https://www.exitfive.com/ 
• Our Episode with Dave Gerhardt: https://open.substack.com/pub/thetransaction/p/ai-idea-starters-influencers-and 
• Carilu Dietrich: https://www.linkedin.com/in/cariludietrich/ 
• Our Episode with Carilu: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Our Episode with Jon: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 
• Udi Ledergor: https://www.linkedin.com/in/udiledergor/ 
• Bill Macaitis:

Alex Raymond is the Founder of AMplify and Host of the Account Management Secrets podcast. Alex joins co-hosts Matt Amundson and Craig Rosenberg for the first major discussion on the podcast of account management and its crucial role in growing revenue and overall company value for SaaS vendors. 

Plus, Alex breaks down how CROs should organize their team, what types of people make for the best account managers, and why in-depth stakeholder mapping of customer accounts is so critical to growing revenue. 

Also, Craig mixes up country singers, Matt discovers a great path, and Producer Sam compares someone’s comment to military ordinance. 

Critical Takeaways

• Account management should be positioned as the "growth department" of your company, responsible for driving profitable revenue from existing customers. Shift the mindset from reactive support to proactive growth, ensuring account managers are empowered and resourced to expand accounts, not just retain them.
• Start building account management capabilities early, even before you hit $10M in revenue, so you can learn from customers, reduce churn, and set the foundation for compounding growth. Don’t wait until churn or customer growth becomes a problem you’re hearing about in your board meetings.
• Ambiguity about who owns customer growth leads to missed opportunities. 
• Great account managers are creative problem solvers with strong business sense, often with consulting backgrounds. They should be able to see the big picture, ask insightful questions, and build long-term relationships, rather than just focusing on renewals or incremental expansions. PS: former consultants make for great AMs.
• Build Robust Stakeholder Maps and Engage at Multiple Levels.
• Vendors need to actually do QBRs (Quarterly Business Reviews). Go talk to your darn customers.

Chapters

00:00 - Episode Preview

01:00 - Trouble with Tickets

03:44 - Introducing Alex Raymond, Founder of AMplify

05:59 - The Role of Account Management in The Growth of B2B Startups

12:27 - The Power of Exponential Thinking for Entrepreneurs

16:01 - A Quick Sidebar about Business Events and Dining in Boulder

19:31 - Why Account Management is a Revenue Function & When Your Startup Needs Account Managers

29:15 - Where Account Management Should Fit in Your Revenue Team’s Organizational Design 

36:26 - What To Look for When Hiring Great Account Managers

42:03 - When Account Managers Should Be Brought into New Deals

49:13 - Developing Complex Stakeholder Maps for Customer Accounts

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “ The CRO should be managing the entirety of their revenue cycle, not just some slice of it.” - Alex Raymond
• “ Land and expand has never been more important than it is right now.” - Alex Raymond
• “ I just never, ever want to be a CEO.” - Matt Amundson

Connect with Alex

• LinkedIn: https://www.linkedin.com/in/afraymond/ 
• Website: https://www.amplifyam.com/ 
• Podcast: https://www.amplifyam.com/podcast 

Shoutouts

• Craig’s Episode on Alex’s Podcast: https://www.amplifyam.com/account-management-secrets/why-post-sale-is-still-broken-and-what-to-do-about-it-craig-rosenberg 
• Mike Rapp: https://www.linkedin.com/in/michaelrapp-intelepeer/ 
• Alex’s Episode with Mike Rapp: https://www.amplifyam.com/account-management-secrets/serve-retain-sell-how-account-management-builds-revenue-leaders-mike-rapp 
•  Dr. Benjamin Hardy: https://www.linkedin.com/in/drbenjaminhardy/ 
•  Conscious Entrepreneur Summit: https://consciousentrepreneur.us/ 
• The Science of Scaling by Dr. Benjamin Hardy & Blake Erickson: https://a.co/d/eTUlHeV 
• 10x is Easier Than 2x by Dan Sullivan & Dr. Benjamin Hardy: https://a.co/d/1kf8tSe 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Here to help illuminate and elucidate the role of AI agents is Gabe Larsen, the Chief Revenue Officer at Signals and the former Chief Marketing Officer of Kustomer. 

Gabe joins co-hosts Matt Amundson and Craig Rosenberg for a deep dive into how agentic AI coupled with signal-based marketing succeeds in go to market where Account-Based Marketing failed in its execution. We get into whether startups should build or buy the tools they need, which new metrics your board might be looking for, and what customers really want to hear about from vendors.

Plus, Gabe bids goodbye to the age of software tools while welcoming in the AI-powered teammate economy.

Also, Craig vehemently denies accusations of scowling, Matt shares his preferences on the intricacies of the English language, and Producer Sam asks a dumb question.

Critical Takeaways

• Agentic AI tools need to provide omni-channel execution in order to offer real value and impact to sales and marketing teams. 
• The combination of Signals + Agents outperforms Account-Based Marketing in the way it has been traditionally deployed. However, the core ideas of ABM, such as Ideal Customer Profiles, Target Accounts, Personalization, etc., still hold true. In fact, the advances in AI-powered martech have now made the original promise and vision of ABM possible.
• In the build vs buy debate, much of what has been built and is being built in-house is far too brittle to accommodate the regular use of a revenue team. You don’t want your whole custom-built workflow to break every time someone makes a minor change to something as small as an email subject line. However, the solutions that are going to succeed and ultimately be bought must be capable of handling the custom needs and workflows of the users. If the available tools are too rigid for customers, then they will look to build their own workarounds, solutions, and eventually, replacement tools.
• As the “customization economy” takes hold, go-to-market teams should seek vendors that offer flexible, customizable solutions rather than rigid, templatized products. From the vendor side, take note that buyers are gravitating toward platforms that allow them to tailor workflows to their unique needs, and if you fail to provide this flexibility, you will be left behind.
• Customers crave real guidance from vendors, not just hype about the new features you added. The most successful vendors will be those who offer clear, prescriptive playbooks and best practices (Think HubSpot or Marketo).

Chapters

00:00 - Episode Preview

02:16 - Introducing Gabe Larsen, the Chief Revenue Officer of Signals

04:53 - Learning The Costly Difference between Michael and Michelle 

09:23 - Catastrophic Sales Kickoff Stories

14:26 - The Dim Sum Disaster

17:29 - Why Signals-based Marketing + AI Agents are outperforming Traditional Account-Based Marketing

26:15 - Builders versus Buyers & Why Tools are Out and Teammates are In

31:56 - The Role of AI in Modern B2B Marketing

45:01 - The Future of AI-Powered Workforces

48:14 - An AI Vendor's Perspective on Pricing for AI Tools & AI Agents

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “The market’s separating into builders and buyers and I think we’re establishing more buyers.” - Gabe Larsen
• “ Tools are gone, teammates are in.” - Gabe Larsen 
• “This is the customization economy” - Craig Rosenberg

Connect with Gabe

• LinkedIn: https://www.linkedin.com/in/gabelarsen/ 
• Signals Website: https://getsignals.ai/ 

Shoutouts

• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• David’s Boskovic’s episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-market

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Market and AI strategies. Davis joins co-hosts Matt Amundson and Craig Rosenberg for an exploration of the current state of ABM (Account-Based Marketing), what it takes to drive impact of using AI in GTM Execution, and how to right-size the B2B marketing tactics to each account. 

Also, Craig uses a ‘Matt-ism’, Matt distinguishes cuddling from canoodling, and Producer Sam fixes a problem with his face. 

Critical Takeaways

• There are three core account-based marketing models: Enterprise ABM (1:1 and 1:few), Growth ABM (1:many at scale), and Deal Acceleration (targeted support for individual opps).
• Shift from short, one-off marketing campaigns to holistic, always-on programs that run continuously throughout the year. Build a playbook of ABM tactics (e.g., webinars, executive dinners, personalized landing pages, LinkedIn ads) and deploy them based on account tier and industry segment. This enables ongoing engagement and better adapts to complex B2B buying cycles.
• Select and tier accounts based on informed revenue potential, not just logo desirability or gut feel. Analyze first, second, and third-party signals, as well as customer LTV and microsegments, to prioritize accounts for deeper personalization and resource allocation. For example, reserve direct mail and executive engagement for tier one, while using scalable digital tactics for lower tiers.
• Unify your target account lists across sales, marketing, and customer success to drive alignment and efficiency. Instead of each function working from separate lists, create a single Go-To-Market account portfolio informed by revenue potential and engagement signals. 
• AI can dramatically accelerate research, content personalization, and account list building, but only if you have a clear strategy first. Many companies are underutilizing AI or using it without a defined goal, leading to mediocre results.

Chapters

00:00 - Introducing Davis Potter, Founder of ForgeX

08:00 - Quick Coldplay Concert Conundrum Recap

10:00 - Davis’ first ABM Webinar horror story

16:00 - Redefining Account-Based Marketing: Beyond the traditional pyramid

18:00 - A new ABM segmentation model

24:00 - The case for a unified Go-To-Market account portfolio

27:00 - Growth ABM tactics that actually scale

31:00 - Where AI fits into an ABM strategy  (and where it doesn’t)

39:00 - How shadow AI is reshaping GTM

45:00 - Reporting, the board deck problem, and the MQL hangover

49:00 - What your Revenue Team needs to measure in modern ABM

53:00 - Replacing the Market Qualified Lead industrial complex

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “One practitioner can't cover 50 accounts and actually leverage one-to-one.” - Davis Potter

Connect with Davis

• LinkedIn: https://www.linkedin.com/in/davispotter62/ 
• ForgeX Website: https://www.forgex.ai/ 
• Revenue Xchange: https://open.spotify.com/show/7v2449do8UGuLAbilezi29?si=1a56c9a9a18d4550 

Shoutouts

• Demandbase
• Sangram Vajre: https://www.linkedin.com/in/sangramvajre/
• Sam McKenna: https://www.linkedin.com/in/samsalesli/ 
• Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge 
• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan Gottlieb’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Kerry Cunningham: https://www.linkedin.com/in/kerrycunningham/ 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 

Jon Miller’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 

Plus, Rachel reveals what happened when she gave a friend some less-than-amazing career advice.

Also, Craig reveals his fondness for a certain slightly disparaging epithet, Matt releases his pent-up rage, and Producer Sam vows to make certain edits to the episode. 

Critical Takeaways

• Building relationships with industry analysts at research firms, such as Gartner or Forrester, is only getting more important for B2B startups and scale ups. By the way, ‘building a relationship’ in this context is not code for just paying to play; we mean actually fostering real human connections with individual analysts, even before you think about paying a dime for a subscription for their firm.
• If you want your SaaS startup to show up in things like industry analyst reports and ‘magic quadrants’, start by finding and reviewing the evaluation criteria for those reports, which are publicly available. Bonus tip: try to get involved early when criteria are being set. 
• For the ‘self scout’ of your product against the analyst’s criteria, bring in a few PMs (Product Managers) and SEs (Sales Engineers) to help you do a brutally honest self‑assessment, find weak spots, and see what shifts can be made. SEs are great resources to bring in because they are hyper aware of the critical issues with their own product and can provide clear-eyed insights.
• Pick one use case, one ICP (Ideal Customer Profile), and one persona to focus your go-to-market strategy on. Trying to be all things to all customers from day one is a recipe for dilution of your brand and burnout. Choosing one target (even if it feels narrow or imperfect) lets you focus your go-to-market resources, refine messaging, and build momentum for your company.
• Your first marketing hire should be a Product Marketer, not a demand gen specialist. Startups need someone who can define and refine messaging, narrative, positioning, not just pushing leads to sales. Without a clean story, demand gen spends often under‑deliver.
• With analysts, frequent light engagements, such as updates about new clients, features, saas founders turning over data, build familiarity and trust. Much of what shows up later in evaluations or quotes starts with these small, consistent touchpoints.

Chapters

00:00 - Episode Preview

00:50 - Endearing Terms for The Wonderful People from Massachusetts

03:27 - Introducing Rachel Dines, Author & Go-To-Market Advisor (Plus, Former Forrester Analyst)

07:24 - A Quick Convo about Data Centers & The Mission Impossible Film Franchise

10:24 - Giving Your First Solo Presentation as an Analyst with a Heads Up

16:18 - Why Startups Need To Engage The Industry Analysts Early On

20:22 - How Startups Should Approach Their Initial Analyst Relations Strategy

29:35 - Matt Admits What Grinds His Gears

31:23 - What Early Stage Startups Can do to Become Number One in the Magic Quadrant

34:08 - Startups Should Start with One Segment, User, and Use Case

46:51 - Why Your First Marketing Hire Should be a Product Marketer

52:21 - Some not so great B2B Marketing career advice

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “Focus, in the Go-To-Market side especially, is always the greatest Achilles heel of so many startups” - Rachel Dines
• “Pick a lane and win” - Matt Amundson
• “I can be bought for tiramisu” - Rachel Dines

Connect with Rachel

• LinkedIn: https://www.linkedin.com/in/rdines/ 
• Substack: https://racheldines.substack.com/ 
• Website: https://www.racheldines.com/ 
• How I Hacked the Moon: https://a.co/d/eSYYRWG 

Shoutouts

• Scott Mersy: https://www.linkedin.com/in/smersy/ 
• Sam McKenna: https://www.linkedin.com/in/samsalesli/ 
• Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge 
• Mission: Impossible - Rogue Nation (Christopher McQuarrie, 2015)
• The Studio (Apple TV+)
• Last Week in AWS (Newsletter): https://www.lastweekinaws.com/ 
• Corey Quinn: https://www.linkedin.com/in/coquinn/ 
• Cursor
• Windsurf
• Lovable
• Chris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ 
• Snowflake
• Denise Persson: https://www.linkedin.com/in/denisepersson/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

To provide a refresher on those basic B2B sales skills and more, we’re thrilled to introduce Tom Murtaugh, the Portfolio Operations Director at Nordic Capital, a leading sector-specialist private equity firm. Tom joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of maintaining deal control, why revenue leaders need to understand the key activities that drive outcomes, and how to get your sales managers up to speed as they become more valuable with the implementation of AI.

Plus, Tom helps Craig and Matt perform an autopsy on the failure of the sales enablement movement.

Also, Craig once again references TOPO and Matt gets envious of a warm male embrace while also imparting the joys of parenthood.

Critical Takeaways

• What are the handful of activities that have a real impact on moving a deal forward for your company? While most organizations cannot empirically state which activities drive revenue, using modern data tools and call analysis, sales leaders can and should run correlation analyses to pinpoint and scale what top performers do.
• Sales leaders should be directly involved in late-stage enterprise deals, ensuring there is a clear, actionable joint execution plan for each opportunity. Top-down focus and hands-on deal reviews with sales leaders is critical to exceeding targets, even when the forecast looks grim. This level of engagement cannot be delegated or replaced by process alone.
• AI can accelerate analysis and experimentation, but it cannot define your core GTM motions or fix broken processes. If you haven’t figured out what works, AI will only amplify confusion. Go-To-Market leaders must first establish and validate the key behaviors and activities that move the needle before layering on automation or analytics. 
• Sustainable revenue growth comes from robust GTM infrastructure, such as processes, platforms, and RevOps, that persist beyond any single CRO or sales leader.
• Sales enablement programs often fail when led by people without quota-carrying experience, devolving into classroom-style training that sellers reject. Shift to “sales excellence” roles, where former sales leaders who coach reps in the field, ride along on calls, and provide practical, trusted guidance. 
• The most powerful enablement tools are those that let reps learn directly from top performers, such as reviewing Gong calls or shadowing high achievers. Tom shared that new reps who proactively sought out and emulated top sellers ramped faster and performed better. Make it easy for your team to access and learn from real sales conversations, not just static content.

Chapters

00:00 - Episode Preview

03:51 - Introducing Tom Murtaugh, Portfolio Operations Director at Nordic Capital

10:09 - How Improving Deal Control Turned Around a Terrible Quarter for Collibra

21:02 - Understanding the Key Activities that Really Drive Outcomes in B2B Sales

28:21 - Why Training First Line Sales Managers Needs to be a Priority for B2B GTM Leaders

42:29 - Why the Sales Enablement Movement Ultimately Failed in Improving B2B Sales Orgs

51:21 - The Role of RevOps in Building a Sustainable Infrastructure for the Revenue Organization

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “Any type of conversational analytics tool is the most powerful enablement tool that's out there right now, and people just need to use it.” - Tom Murtaugh
• “ Your sales manager is be going to become incredibly, even more important than they are today, because they're going to be the ones that even with a little bit of change, are going to have a lot of leverage over a lot of people.” - Tom Murtaugh

Connect with Tom

• LinkedIn: https://www.linkedin.com/in/tom-murtaugh-1729b09/ 
• Nordic Capital Website: https://www.nordiccapital.com/ 

Shoutouts

• Amanda Murtaugh: https://www.linkedin.com/in/amandabuck143/ 
• Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ 
• Philip Cardi
• Neil Harrington: https://www.linkedin.com/in/neildharrington/  
• Scott Albro: https://www.linkedin.com/in/scottalbro/  
• Jeff Goree: https://www.linkedin.com/in/jeffgoree/ 
• Andy Byrne: https://www.linkedin.com/in/byrneandy/ 
• Michael Hargis: https://www.linkedin.com/in/mhargis/ 
• Pablo Dominguez: https://www.linkedin.com/in/pabtexas/ 
• Echo Valley on Apple TV+ Starring Sydney Sweeney & Julianne Moore (Only rated a 6.3/10 on IMDb)

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Critical Takeaways

• Investing only in Sales Process is not enough to help sellers hit their targets, because process only covers what to do. Whereas, Skill capacity doesn't stop at what to do. Skill capacity is what to do, why to do it, and how to do it so that you're building judgment. This way, reps can have audible-ready, rich business conversations that create value for both buyers and customers.
• When training sales reps on new skills, it’s best to make sure they master one skill before they move on to learning another. This builds skill depth, rather than very shallow skill breadth. Without ensuring competency in one skill before moving on, all you achieve is motion without accomplishment.
• The first, foundational skill that reps should train on is sales discovery. Having a strong grasp on discovery will help sales reps build stronger additional skillsets. It’s harder to build the other sales skills without having a solid understanding of sales discovery.
• As companies’ go-to-market motions become increasingly complex, if they don’t address the low skill capacity of their sales team, they incur a growing ‘skill deficit’, which if left unchecked will lead to catastrophic results down the line.

Chapters

00:00 - Episode Preview

02:21 - Introducing Chris Orlob, CEO of pclub.io

03:33 - An Instructive B2B Sales Story: How to Interact with Procurement Leaders

08:06 - Craig & The Case of The Bloody-Eyed Business Meeting

12:19 - The State of the B2B Sales Skills Crisis in Go-To-Market Today

25:40 - Discovery is the Fundamental Sales Skills Reps Need to Learn

33:24 - How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market

44:25 - Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' Training

Join our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “We are in an era of a Go-To-Market skills crisis.” - Chris Orlob
• “Reps and sellers are drowning in technology, but starving for skills and skill capacity.” - Chris Orlob
• “AI is not the solution to the skill gap.” - Craig Rosenberg
• “If they can't build a case for me of how they're going to solve my problem, I don't really want to buy it.” - Matt Amundson

Connect with Chris

• LinkedIn: https://www.linkedin.com/in/chrisorlob/ 
• pclub.io Website: https://www.pclub.io/
• Twitter: https://twitter.com/Chris_Orlob 

Shoutouts

• Chris’s Last Episode on The Transaction: https://thetransactionpod.com/episodes/to-gate-or-not-to-gate-content-with-chris-orlob-the-transaction-ep-005 
• Scott Albro: https://www.linkedin.com/in/scottalbro/  
• Paul Rosenberg: https://www.linkedin.com/in/paul-rosenberg-0970421/ 
• Ryan Tibbetts: https://www.linkedin.com/in/ryantibbetts/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. David joins co-hosts Matt Amundson and Craig Rosenberg to outline how he and the GTM team at Flatfile developed their new AI-first go-to-market strategy, which is handling ten times the capacity of their previous GTM motions.

David shares which of the 3 ways AI is being deployed works best, why you need to hire for individual contributors based on a candidate’s tastes, and why every Rev Ops team needs to hire an AI Engineer in order to stay ahead of the curve.

Plus, David regales Matt and Craig with potentially the greatest story that’s ever been told on The Transaction, perhaps even better than ‘Maggots on a Plane.’

Also, Craig threatens someone with having to wear a raccoon costume, Matt reveals the secret of what makes Craig great, and Sam the Producer experiments with some AI artwork.

Critical Takeaways

• When segmenting your ICP, segment into micro-verticals of 100–500 accounts, so you can then build tailored value propositions, demos, and collateral for each. AI allows this “luxury” level of personalization, which was once reserved for top accounts, to be applied to all targets. This dramatically improves first-call resonance, increases conversion rates, and differentiates your solution in competitive enterprise sales cycles.
• AI now allows you to turn things like costly enterprise-grade research into a commodity. Using tools like ChatGPT’s Deep Research or Perplexity you can produce insightful 40+ page market and account reports in hours instead of weeks. Validate quality by testing it with actual prospects. This “luxury” level of diligence, previously reserved for only top-tier accounts, can now be applied to every target at low cost.
• Having a CRM isn’t good enough. You should use AI to index every past customer/prospect interaction and extract key insights (budgets, pain points, workflows). Make this context instantly available to reps so every future conversation builds on a rich historical foundation.
• Every RevOps team, regardless of size, needs an AI Engineer to rapidly prototype and operationalize AI tools internally. If you want to remain ahead of the curve, you can’t be beholden to the slow development and innovation of tools from other SaaS companies.
• Operationalize everything in the company like a product. Treat your revenue org like a software system, debug bottlenecks, design orchestrations, and continuously iterate. The faster your GTM processes can be updated, the faster you can capitalize on new AI capabilities as they emerge.
• There are three main ways AI is deployed, Automation/Replacement, Augmentation, and Amplification. Amplification gives you the largest potential outcomes. To use the Amplification approach, deconstruct every GTM role into component tasks, give repetitive or low-value ones to AI, and keep humans focused on peaks of expertise like judgment, taste, and relationships.

Chapters

00:00 - Episode Preview

01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile

02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company

11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch 

15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability

22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness

33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer

39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best

47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement

51:34 - Sam Debuts Some Interesting AI Artwork of David

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Epic Quotes

• It is incredibly hard to be optimistic enough about what’s possible” - David Boskovic
• “Dream your wildest dreams and see if you can make them happen. And if not, put them on the shelf, not for a year, but for a few weeks.” - David Boskovic
• “Part of what makes Craig great is his curiosity. He’s a lifetime learner.” - Matt Amundson

Connect with David

• LinkedIn: https://www.linkedin.com/in/dboskovic/ 
• Website: https://flatfile.com/ 

Shoutouts

• Rory O'Driscoll: https://www.linkedin.com/in/roryodriscoll/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Endgame: https://www.endgame.io/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

We are thrilled to welcome back AI and marketing expert Sydney Sloan, the Chief Market Officer of G2, to the program on this episode. Sydney joins Co-Hosts Matt Amundson and special Co-Host Scott Albro to explore how AI is being used by buyers when making purchasing decisions, the transition from SEO (Search Engine Optimization) to GEO (Generative Engine Optimization), and where business opportunities are emerging along the ‘AI Gradient.’ Plus, we get into some super tactical ways to improve your review strategy to increase trust and show up in AI search results.

Also, Matt fawns over Cursor once again, Scott asks about tweeting at Founders, and Sam The Producer mercilessly throws Craig squarely under the proverbial bus.

Critical Takeaways

• 80% of buyers now use AI as part of their research process. In order to actually show up in results from an LLM, brands must embrace Generative Engine Optimization (GEO) by creating and optimizing brand content for people and problems, not just keywords.
• The best way to get more customer reviews is to embed review prompts in-app via tools like Medallia, Pendo, or Qualtrics. This leads to higher volume, verified reviews without incentives. Work with your product team to operationalize in-app review capture.
• To influence LLM outputs and improve buyer relevance, encourage customers to describe their specific use cases when writing reviews. This increases your company’s discoverability in AI-generated comparisons and rankings.
• Encourage founders and leaders to engage with reviews and even respond directly, this signals customer obsession and builds brand trust. Ps. you can pipe G2 reviews directly into Slack (Which is what Kyle Porter did at Salesloft).
• As AI agents become more integrated into your tech stack, you’ll start to feel the emerging need for an “AI architect” role in RevOps. This person would manage prompt engineering, agent workflows, and orchestration across sales, marketing, and customer systems.

Chapters

00:00 - Episode Preview

00:48 - Introducing Sydney Sloan, Chief Market Officer at G2

04:15 - The Emerging Go-To-Market Playbook & New B2B Buyer Behavior Study

11:25 - How to Use G2 to Rank Your Brand in ChatGPT Results for Best SaaS Tools

 15:11 - What Makes G2 Reviews Stand Out & Why You Should Always Respond to Customer Reviews

 18:46 - How Founder-Led Companies are Using Customer Reviews Creatively

21:59 - How Buyers are Using AI Tools In Their Buyer Journey & To Compare Solutions

26:47 - How Generative Engine Optimization Helps Your Brand Show Up in AI Search Results

31:59 - Why Enterprises are Using AI Tools More Than Startups

33:53 - The Meteoric Rise of Cursor & Which Categories or Niches are Ripe for AI Disruption

44:24 - The AI Gradient & Why You Need an AI Architect on Your RevOps Team

50:21 - Throwing Craig Under The Bus For Causing a Technical Issue & Wrapping Up

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Epic Quotes

• “What we did six months ago is definitely not what we're going to do six months from now.” - Sydney Sloan
• “If you haven't yet started thinking about how do you show up in the LLMs, you're behind.” - Sydney Sloan
• “I don't think you can put all of AI generically into the hype cycle. I think you have to look at it by category or use case.” - Scott Albro
• “People use different language in LLMs than they do in search engines.” - Matt Amundson

Connect with Sydney Sloan

• LinkedIn: https://www.linkedin.com/in/sydsloan/ 
• G2 Website: https://www.g2.com/ 
• G2.ai: https://ai.g2.com/ 
• Putting AI Into Action Roadshow: https://sell.g2.com/ai-in-action-roadshow 

Shoutouts

• Kyle Porter: https://www.linkedin.com/in/kyleporter/ 
• Kyle’s Episode of The Transaction: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers 
• Tim Sanders: https://www.linkedin.com/in/sanderssays/ 
• Guillaume Cabane
• Cursor: www.cursor.so
• Qualified: www.qualified.com
• Clay: www.clay.com
• HubSpot: www.hubspot.com
• 1mind: www.1mind.com
• Salesloft: www.salesloft.com
• Gong: www.gong.io
• Iron Mountain: www.ironmountain.com
• Airbnb: www.airbnb.com
• Waze: www.waze.com
• Uber: www.uber.com
• Lovable: www.lovable.so 
• Windsurf: www.windsurf.ai 
• Waymo: www.waymo.com 

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Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale. Brent is back alongside Co-Hosts Matt Amundson and Craig Rosenberg to share how sellers can help B2B buyers become more confident in their own buying decisions, why “frame making” needs to be part of every seller's mindset, and how to tell powerful, emotionally engaging stories.

Also, Craig confronts his own fleeting mortality, Matt says he likes “the big pullout”, and Sam the Producer contributes by swearing.

Critical Takeaways

• Modern B2B buyers are overwhelmed and uncertain. Top-performing reps succeed by helping buyers build self-confidence in their decisions, not by pitching harder or throwing more whitepapers at them.
• The biggest predictor of successful SaaS deals isn’t objection handling, it’s whether the buyer believes they’re making a good decision. Sales teams should focus on guiding internal alignment and validating the decision process.
• Stop selling like you’re the expert and start selling like a guide. SaaS buyers want to see and hear what similar companies are doing when in their position. Social proof beats thought leadership when it comes to moving deals forward.
• Customer indecision is the real killer of your pipeline. B2B Buyers who feel overwhelmed delay action, your job is to make progress feel easy and safe.
• GTM leaders should train reps to speak with emotional clarity, using language that reflects how buyers feel, not just what they need to know.
• AI can’t replace human trust in B2B sales. Even as automation takes over task work, the real differentiator in SaaS GTM will be emotional connection and the ability to de-risk complex decisions.
• Vulnerability builds trust. Whether it’s storytelling, deal coaching, or just acknowledging awkward moments, honesty closes more than clever pitches.

Sponsored Segment

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 - Episode Preview

02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story

06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines

12:26 - The Origins of Brent’s Latest B2B Sales Research

16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling

19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals

26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently

31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward

37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects

41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions

48:32 - The Key to Telling Compelling, Emotionally Engaging Stories

53:25 - How Addressing the Elephant in the Room, like Bloody Eyeballs, can Create Better Human Connections  

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Epic Quotes

• “ When things like that make you nervous, uncomfortable, you don't run away from them you have to run right at 'em.” - Brent Adamson

Connect with Brent Adamson

• LinkedIn: https://www.linkedin.com/in/brentadamson 
• The Framemaking Sale: https://a.co/d/iQhqSzq 
• Website: https://www.brentadamson.net/ 
• A to B Insights Website: https://atobinsight.com/ 

Shoutouts

• Brent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer
• Coffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 

From dissecting permission-based openers to dunking on dated tactics, sales experts Justin Michael and Charles Needham make a bold case for why the phone isn’t dead as a sales channel—it’s just misused. 

Justin Michael, aka the John Wick of executive coaching, is a longtime B2B seller and sales trainer, as well as the Founder of the Justin Michael Method and co-author of The Cold Call Algo. Along with being Justin’s Co-Author on Cold Call Algo, Charles Needham is a bona fide B2B Sales Badass in his own right, being the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Joining co-host Matt Amundson for this episode, Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools.

Critical Takeaways

• Encouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships.
• The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement.
•  Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes.
• Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation.

Chapters

00:00 Intro

01:09 Introducing Justin Michael and Charles Needham

02:55 Discussing B2B Sales Strategies and Cold Calling as an effective sales channel

03:37 Justin's B2B Sales Stories and Experiences

08:07 Charles on Modern Sales Challenges for SaaS Startups

13:22 The Emerging Role of AI in B2B Sales Today

17:10 Cold Calling Sales Techniques and Best Practices

30:29 Debating Cold Call Openers

32:53 Unified Theory of Cold Calling for B2B sales

39:03 Mastering Tonality and Rhythm during B2B Sales Calls

56:26 The Future of Cold Calling

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Epic Quotes

• “Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham
• “Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham
• “ People buy emotionally, they justify with logic.” - Justin Michael

Connect with Justin Michael

• LinkedIn: https://www.linkedin.com/in/michaeljustin/ 
• Website: https://www.salesborgs.ai/ 
• Get the Book: https://coldcallalgo.com/ 

Connect with Charles Needham

• LinkedIn: https://www.linkedin.com/in/charles-needham/ 
• TitanX Website: https://www.titanx.io/ 

Shoutouts

• Kai-Fu Lee: https://www.linkedin.com/in/kaifulee/ 
• AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee: https://a.co/d/ex6F2Yz 
• David Dulany: https://www.linkedin.com/in/davidkdulany/ 
• Wyzer.ai
• Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ 

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Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. 

Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts.

Critical Takeaways

• Train your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills.
• Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity.
• Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team.
• Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account.
• AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. 
• Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities.
• Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children.

Chapters

00:00 - Episode Preview

00:36 - The Fast & The Furious: Silicon Valley Drift

07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI

11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 

13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer

16:08 - The Power of Building Custom AI Agents for Revenue Growth

22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact

30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market

37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It?

42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI Advancements

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Epic Quotes

• “Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap
• “The goal are the outcomes, not the activities.” - Jake Dunlap
• “Outbound never ends. You cannot take a project-based mindset to outbound.”  - Jake Dunlap

Connect with Jake Dunlap

• LinkedIn: https://www.linkedin.com/in/jakedunlap/ 
• Website: https://skaled.com/ 
• The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller 

Shoutouts

• Dirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u 
• NotebookLM: https://notebooklm.google/ 
• The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 
• Matt Heinz: https://www.linkedin.com/in/mattheinz/ 
• Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• The Club: https://store.winner-intl.com/the-original-club-p2.aspx 

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 This is the first edition of The Direct Deposit presented by The Transaction.
========================================
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Craig and Matt get Scott talking about everything from AI-driven storytelling to "vibe marketing," with detours through SDR history lessons, Red Bull stunts, and the existential crisis of printer ownership. If your go-to-market motion still depends on intent data and white papers… this episode might hurt (in a good way).

Also, Craig breaks his keyboard, Matt mentions a little company he likes to call Red Bull, and Producer Sam desperately attempts to curry favor with Scott.

Critical Takeaways

• The next wave of breakout companies will be driven by founders who embed themselves deeply into the Go-To-Market engine, not just product. Founder-led GTM creates authenticity, speed, and unmatched customer resonance.
• High-performing Go-To-Market teams in SaaS-land are shifting from one-size-fits-all playbooks to an experimentation mindset. It’s about making bold bets, measuring ruthlessly, and scaling what works, not chasing the hack of the week.
• Most so-called intent data is internet exhaust, not evidence of real purchase behavior.
• The best GTM orgs lead with narrative clarity, tying their solution to a broader shift in the world, anchoring it in customer pain, and delivering it with conviction. Skip this, and no one remembers you.
• Stunt marketing has a place in B2B SaaS. Think viral launches, bold storytelling, and emotional engagement. It’s not about gimmicks, it’s about being memorable in a world flooded with sameness.

Chapters

00:00 Episode Preview

03:30 – The Go-To-Market Founder Concept

07:00 – How Modern Go-To-Market Orgs Win

13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers

17:00 – Crafting a Resonant Story for your B2B brand

21:00 – Aligning Product and Go-To-Market Motions (Finally)

25:00 – Convincing B2B Startup CEOs to Experiment

30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate

36:00 – Storytelling Frameworks That Actually Work for Startups

42:00 – Lethal Weapon Posters and Swarms of Bees

Epic Quotes

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Epic Quotes

• “If you're not reinventing your Go-To-Market org, you need to have a look in the mirror.” - Scott Albro
• “Founders can just do things that other people can't.” - Scott Albro

Connect with Scott

• LinkedIn: https://www.linkedin.com/in/scottalbro/ 

Shoutouts & Resources Mentioned

• Skosh: https://www.merriam-webster.com/dictionary/skosh 
• Skosh Usage over time: ​​https://books.google.com/ngrams/graph?content=skosh%2Csmidge%2Ctad%2Ciota%2Cmodicum%2Cwhit%2Cscruple%2Csmidgeon%2Cwee%2Cfathom&year_start=1800&year_end=2022&corpus=en&smoothing=3
• Bland
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/ 
•  Lena Waters: https://www.linkedin.com/in/lenawaters/

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Also, Matt reveals his devious guilty pleasure and Craig shares how he lost his children in the desert.

Critical Takeaways

• 
  Instead of prompting AI like a search engine, leaders should teach their teams to treat it like a colleague. Matt’s breakthrough came when he asked ChatGPT how to build personas and what information it needed to do so. By asking “how do I build X?” instead of “give me X,” teams unlock faster, higher-quality outcomes.
• Adopt a “Shock & Awe” mindset to break through. The market is saturated and fatigued—practical content alone isn’t enough. As Craig put it, GTM teams need to pair insight with surprise to break buyers’ patterns. Leaders should push teams to experiment with bolder formats, storytelling, or AI-powered personalization that “breaks the frame.”
• Account Research with AI is now table stakes for sales and marketing teams. Using AI for account research (before, during, and after sales calls) is no longer optional. Craig emphasized this is the new baseline expectation. If your team isn’t using tools like ChatGPT or Perplexity to prep on accounts and individuals before outreach, you’re behind.
• Before adopting any AI vendor solution, ask: “Can my team do this directly in ChatGPT or another general model?” As Craig noted, many startups at SaaStr were pitching account prep workflows that anyone can already do with a simple prompt.

Chapters

00:00 Episode Preview

03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working

06:15 Building a New Playbook with AI in the Go-To-Market Hacker era

08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback

13:15 Talk to Your AI Tools Like People 

17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor

25:30 Account Research is the New Minimum – How GTM teams are winning with better prep

30:00  Matt & Craig just Want to Watch the World Burn

37:00 Events Are Back, Baby – People crave new insights and in-person energy

40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands

45:00 Video Content: Raw vs. Polished – When it’s time to scale production (and when DIY still wins)

50:00 Lost in the Desert: A GTM Parable – Craig’s real-life ATV crisis ends with a 10-year-old roasting him

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Epic Quotes

• “ It's the age of the Go-To-Market hacker.” - Craig Rosenberg
• “ Everybody needs to create a custom GPT. And if you want to know how to do it, just ask it. How do I create a custom GPT here?” - Matt Amundson

Shoutouts

• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Kristina McMillan: https://www.linkedin.com/in/kristinamcmillan/ 
• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• Jill Rowley: https://www.linkedin.com/in/jillrowley/ 
• Jill Rowley’s tweet calling Craig’s Blackberry in 2012: https://x.com/jill_rowley/status/187231284970536960 
• SaaStr
• Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ 
• Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ 
• Copy.ai
• Klarity: https://www.klarity.ai/ 
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Mandy Dhaliwal: https://www.linkedin.com/in/1mandydhaliwal/ 
• Jake Dunlap: https://www.linkedin.com/in/jakedunlap/ 
• James Kaikis: https://www.linkedin.com/in/jameskaikis/ 
• Jordan Crawford: https://www.linkedin.com/in/jordancrawford/ 
• Jordan’s Episode: https://open.substack.com/pub/thetransaction/p/inverting-your-go-to-market-strategy?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false

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Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements. 

Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word.

Critical Takeaways

• Events are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage.
• Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiences
• Prospects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind.
• Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet.

Chapters

00:00 - Episode Teaser

00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater

10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ

13:46 - Lessons to Learn from the Worst Sales Experience Ever

25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals

30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists

35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid

39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands

44:44 - Thinking Beyond the Booth When Planning out Your Event Strategy

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Epic Quotes

• “ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman
• “If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman
• “I rub the thing” - Craig Rosenberg

Connect with Amy

• LinkedIn: https://www.linkedin.com/in/aholtzman/ 
• Website: https://cheq.ai/ 

Shoutouts

• Every Little Step I Take by Bobby Brown: https://youtu.be/P0FKzPfsxA4?si=o3k9Iepu3KwnP1Aa 
• Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ 
• Jessica Lin: https://www.linkedin.com/in/jessicalin8/ 
• Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq 
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-report
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements.

Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world.

Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion.

Critical Takeaways

• Identify specific, narrow segments by understanding unique heuristics that indicate a need for your product. For instance, identifying complex sales teams with high traffic who would benefit from LeanData's routing solutions is more effective than broad targeting.
• You need to understand your customers and their pain before bringing in tools like Clay or ZoomInfo. Sales leaders should spend time with SDRs to gain insights on what truly resonates with prospects, ensuring that any data or tools used are enhancing proven strategies rather than replacing deep understanding.
• The burden placed on SDRs to make sense of complex data without adequate support is a recurring issue. Leaders should simplify data insights and ensure SDRs are equipped with actionable, digestible information, alleviating stress and improving effectiveness. 
• Adopt a 'pain-qualified' segmentation approach. Identify segments that not only fit demographic profiles but also exhibit specific pain points that your product can address, such as complex routing needs in high-traffic sales teams for LeanData. This ensures messages are highly relevant and more likely to result in conversions.

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 Introduction: The Intimidating Box

01:07 Mr. Pickles and Misadventures in Pocket Dialing

04:42 Craig’s Midlife Go-To-Market Crisis

05:31 What’s broken with the Old Go-To-Market Playbooks

07:30 What is The New World of Sales and AI

13:04 Segmenting and Targeting with Data

16:43 Permissionless Value Prop in Action

23:25 The List is the Message

25:47 Methodology and AI Integration

26:55 Understanding Customer Segments

29:56 Challenges in Sales and Marketing

33:18 Effective Campaign Strategies

35:16 Adapting to AI and Market Changes

38:37 Purpose of Niche Targeting and Success

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “The list is the message.” - Jordan Crawford
• “Never in my life has there been a more intimidating box than the ChatGPT, Claude, Gemini entry box because for the first time in our lifetimes, and maybe human history, we are the limiters.” - Jordan Crawford

New Terms

• Pain Qualified Segment: Two to five unique heuristics, often that imply tension.

Connect with Jordan

• LinkedIn: https://www.linkedin.com/in/jordancrawford/ 
• Website: https://blueprintgtm.com/ 
• YouTube: https://www.youtube.com/@BlueprintGTM 
• Jordan’s Latest Course: https://pvp.blueprintgtm.com/subscribe 

Shoutouts

• Scott Albro: https://www.linkedin.com/in/scottalbro/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved! 

Also, Craig ponders the meaning of parabolas, Matt ranks the best men’s hair in B2B Marketing, and Producer Sam gets confused by Craig talking about bats.

Critical Takeaways

• Develop a structured approach to AI adoption in Go-To-Market strategies. Instead of engaging in 'random acts of AI,' organizations should create an accountability chart detailing which jobs are better suited for machines and which require human intervention. 
• Personal connections and credibility can differentiate a brand in a noisy market. Efforts should be made to maintain and build these relationships alongside leveraging scalable technology.
• While marketing attribution is important, it should not solely focus on credit for past actions. It should be used to create a more predictable and reliable path towards future outcomes. Go to market teams need to look at attribution as a tool for driving the right behaviors and actions, rather than merely analyzing past performance.
• Signals, including “intent signals”, need to be understood in context and not treated as immediate leads. Revenue teams should use signals to inform their understanding of where a prospect is in the buying journey, rather than assuming all signals indicate readiness to buy. This nuanced understanding can improve targeting and engagement efforts.
• Even as AI and automation take on more tasks, creativity and strategic thinking remain irreplaceable. Teams should focus on leveraging AI for efficiency while reserving creative and complex problem-solving tasks for human talent. This balance can drive innovation and maintain a competitive edge.

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 Episode preview

00:30 Craig Goes Batty and Some Auction Antics

04:13 Introducing Matt Heinz, President of Heinz Marketing

08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies

19:16 Should CMOs Report Up to CROs in B2B SaaS?

22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet

27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI

37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools

42:11 The Role of Data & The Cloud Data Warehouse in B2B Marketing

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ We shouldn't be guessing anymore, we should be using the agents to tell us how to improve right away” - Matt Heinz
• “ If I have more noise and less time, who am I going to prioritize? It's the people I enjoy. It's the people I trust. It's the people I like. That's going to be a huge differentiator moving forward.” - Matt Heinz
• “ I don't want anybody to think that I'm not down with intent signals. I'm down with signals because right now the hardest thing in the world to do is engage.” - Craig Rosenberg
• “If you are looking for the solution in the tool, you're bound to fail.” - Matt Amundson

Connect with Matt Heinz

• LinkedIn: https://www.linkedin.com/in/mattheinz/ 
• Website: https://www.heinzmarketing.com/ 

Shoutouts

• Bat Tours in Austin: https://www.austintexas.org/things-to-do/outdoors/bat-watching/ 
• Bert Kreischer’s Raffle Story: https://youtu.be/EsCadHpBdkY?si=GDRoQpWQ9B1Z_55l 
• Coffee with Brent & Matt: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 
• Joe Chernov: https://www.linkedin.com/in/jchernov/ 
• Steve Woods: 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 
• Lars Nilsson: https://www.linkedin.com/in/lanilsson/ 
• Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales 
• Ted Purcell: https://www.linkedin.com/in/tedpurcell/ 
• Adam Robinson: https://www.linkedin.com/in/adam-robinson-4b156810/ 
• Adam’s Episode: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal 
• Anthony Kennada: https://www.linkedin.com/in/akennada/ 
• Chris Walker: https://www.linkedin.com/in/chriswalker171/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Mary Meeker: https://www.linkedin.com/in/mary-meeker-5823ba48/ 
• Simbe Robotics
• Mperativ
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Lars Nilsson is the Founder and CEO of SalesSource, but you probably know him from his legendary run as the VP of Global Sales Development at Snowflake. To Craig, Lars is, “one of the masters of the universe in sales development and inside sales and business, and clearly very fit.” Lars joins co-hosts Craig Rosenberg and Matt Amundson to discuss how we got to the current state of sales training and enablement in B2B SaaS, why the GTM Engineer role is the next hire you need to make to improve your revenue team, and whether having B2B sales reps roleplay with AI avatars is the way forward or just a waste of time.

Also, Craig relives stories of his past mastication, Producer Sam fights yet another losing battle, and Matt warns everyone that, “ we're going to go deep. We're going deep.”

Critical Takeaways

• Recognize and elevate the Sales Development Representative (SDR) function within the organization. CEOs and senior leaders should regularly acknowledge the impact SDRs have on pipeline generation. Simple acts of recognition can significantly boost team morale and performance.
• Create a systematic process to gather and disseminate insights and customer feedback from the front lines of sales. SDRs interact with numerous prospects daily, and their feedback can inform product development, marketing strategies, and sales tactics. Ensuring this information reaches executive levels can align the organization’s initiatives more closely with market needs.
• Giving your sales team more ‘at-bats’ to practice and hone their craft results in better sellers. Leverage AI-based tools like role-playing bots to enhance SDR training. These tools can provide a scalable, less intimidating way for SDRs to practice their pitches and objection handling. 
• Encourage cross-departmental learning within your org. Facilitate opportunities for SDRs to learn from other teams, such as marketing, operations, and customer success. This cross-training can develop well-rounded employees and ensure smoother transitions when SDRs move into new roles within the company.
• Consistently produce and share content that showcases successful customer stories and product use cases. Having a dedicated resource person, like the retired beat reporter who worked with Lean Data, can ensure continuous content production that drives engagement and educates prospects.
• Encourage a culture where continuous learning and improvement are part of daily operations. Regularly update training programs and technology stacks, and stay abreast of the latest trends and tools in sales and marketing to maintain competitiveness.

Sponsored Segment

~Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 - Episode Preview

00:35 - Craig Eats like Cookie Monster

03:13 - Introducing Lars Nilsson, the Founder & CEO of SalesSource and Former VP of Global Sales Development at Snowflake

07:46 - The Genesis of Sales Development in SaaS & How it Expanded on Account-Based Marketing Concepts

13:23 - How Xerox Trained Their B2B Sales Team and What Startups Should Learn from Their Success

21:34 - The Emerging GTM Engineer Role & The Impact Its Having on B2B Sales Teams Using AI Tools

34:59 - Should B2B Startups Try to Replicate the SDR Academy from Snowflake

38:17 - How Startup Leaders Can Elevate the SDR Role & Why They Must Show Their Appreciation for this Critical Function

45:42 - The Importance of AI Roleplaying Tools for Training B2B Salespeople

54:11 - Startups Founders Should Play a More Active Role in Developing Their Go To Market Strategy

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ I just think that Snowflake with 300 SDRs today, maybe in two years, they'll have 50. But each one will be able to punch above, like they are five individuals because of all the automation.” - Lars Nilsson
• “ One Go-To-Market engineer today is going to make five SDRs punch like they're 25.” - Lars Nilsson

Connect with Lars

• LinkedIn: https://www.linkedin.com/in/lanilsson/ 
• SalesSource Website: https://salessource.com/ 

Shoutouts

• Stuart Silverman: https://www.linkedin.com/in/stuart-silverman-32132/ 
• Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ 
• Karan Singh: https://www.linkedin.com/in/karan-singh-29269015/ 
• Travis Henry: https://www.linkedin.com/in/travisjhenry/ 
• Brendan Short: https://www.linkedin.com/in/brendan-short/ 
• Pete Kazanjy: https://www.linkedin.com/in/kazanjy/ 
• Jason Vargas: https://www.linkedin.com/in/jasonvargas/ 
• John Barrows: https://www.linkedin.com/in/johnbarrows/ 
• Becc Holland: https://www.linkedin.com/in/beccholland-flipthescript/ 
• Hyperbound: https://www.hyperbound.ai/ 
• Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ 
• Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ 
• Kevin Dorsey: https://www.linkedin.com/in/kddorsey3/ 
• Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ 
• Scott Barker trying to book a meeting with Avarra’s AI Avatar Role Play: https://youtu.be/90EQSxcIhqc?si=gKDiVmsnadrsk_IY 
• Tavus: https://www.tavus.io/ 

Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups.

Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director.

Critical Takeaways

• Implement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team.
• Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours.
• Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs.
• Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals.
• Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency.

Sponsored Segment

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 - Episode Preview

00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds

03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue

06:36 - The Origin Story of Women in Revenue (The group, not the concept)

18:17 - The Immutable Impact Diverse Teams in Business

23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want

31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it

36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers

40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS

44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market Alignment

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein
• “ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer)

Connect with Lauren

• LinkedIn: https://www.linkedin.com/in/laurengoldstein/ 
• Winning by Design Website: https://winningbydesign.com/ 
• Women in Revenue Website: https://womeninrevenue.org/ 

Shoutouts

• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with 
• Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ 
• Shari Johnston: https://www.linkedin.com/in/sharijohnston/ 
• Jen Dimas: https://www.linkedin.com/in/jenpd/ 
• Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ 
• Jim Walker: https://www.linkedin.com/in/jwwalker/ 
• Robert Koehler: https://www.linkedin.com/in/rkoehler/ 
• Radius
• Marketo
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• InsideView
• Babcock Jenkins
• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb 
• Miro
• Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/ 
• Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity 
• Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ 
• Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ 
• Colin Gerber: https://www.linkedin.com/in/colinsgerber/ 
• Socure
• Adam B. Needles: https://www.linkedin.com/in/abneedles/ 
• Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with 
• Annuitas

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.

Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.

Critical Takeaways

• The crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.
• Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.
• As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.
• The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. 
• Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. 

Sponsored Segment

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 - Episode Preview

00:20 - Squishy Pineapples & The 1995 UCLA Bruins

04:01 - Introducing Ana Leyva, GTM Leader at Pear VC

08:29 Selling at B2B Conferences on the Road as a New Mom 

11:32 - Focus on Providing Value, not on Bland “Personalization”

21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks

27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales

34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup

45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “I am sick of personalized emails.” - Ana Leyva
• “I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana Leyva

Connect with Ana

• LinkedIn: https://www.linkedin.com/in/analeyva/ 
• Pear VC Website: https://pear.vc/ 

Shoutouts

• AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ 
• Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ 
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: 
• Chris Orlob: https://www.linkedin.com/in/chrisorlob/ 
• Chris’s Episode: 
• Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ 
• Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ 
• Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCS
• Stevie Case: https://www.linkedin.com/in/steviecase/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Gong
• Scott Barker: https://www.linkedin.com/in/ssbarker/ 
• Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on.

Critical Takeaways

•  NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.”
• Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings.
• Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs.
• Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification.
• Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback.

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com

Chapters

00:00 - Preview & Craig’s Christmas related-shirt

04:21 - The Sometimes Life-saving Impact Founding a Company Can Have

10:03 - Email is a Mostly Dead Channel

14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story

20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact

27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups

33:11 - How Do You Measure the Value Your Product Delivers to Customers & Why Founders Need to Focus on NRR 

35:45 - How to Drive Alignment Between Founders and Their Boards

38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales

45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch?

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila Stafford

Connect with Sheila

• LinkedIn: https://www.linkedin.com/in/sheila-stafford-451976b/ 
• Website: https://www.teamsense.com/ 

Shoutouts

• Fortive
• Vanta
• Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ 
• Brett Queener: https://www.linkedin.com/in/brettqueener/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!