Zak Cherif, Head of Product Marketing at KeyShot, joins Jarod Greene to discuss how he is navigating a shift toward product-led growth while maintaining consistent messaging across a complex sales motion. He explains the challenge of supporting multiple sellers, industries, and use cases without losing clarity.

Zak explains how AI assists his team in enriching data, validating ideal customer profiles (ICPs), and generating better messaging options without increasing headcount. He also emphasizes the importance of collaborating with diverse sales teams and highlights that understanding how people work is just as critical as the messaging itself.

This episode provides a practical perspective on how product marketers can leverage AI to simplify complexity and maintain a customer-first approach as they scale.

In this episode, you’ll learn:

• How to validate ICP faster – Use AI to improve targeting with better data
• Why sellers need different support – Adapt content to how each seller works
• How to stay customer first – Keep decisions grounded in real customer needs

Things to listen for:
(00:00) Introduction

(01:35) Staying customer first in product marketing

(02:22) Shifting toward product-led growth

(03:06) A surprising AI use case in fantasy football

(04:32) When AI became mission-critical

(05:00) Using AI for data enrichment and ICP clarity

(06:00) Scaling messaging across many permutations

(07:38) Finding the right problems for AI to solve

(09:26) AI tools for working faster with limited resources

(10:38) Supporting different sales styles with content

(12:41) Balancing consistency with sales autonomy

(14:25) Practical advice for getting started with AI

(15:34) Building AI features that support creativity, not replace it

Martin Gomez, COO and Co-Founder of Wing, joins Jarod Greene to share how his team built a global workforce powered by both people and AI. He explains how Wing evolved from a vision of digital assistants into a system that helps companies extend their teams and get real work done.

Martin walks through how they use AI to increase productivity, improve customer experience, and anticipate needs before they surface. He also shares why many AI products fall short and how leaders can avoid building solutions that no one truly needs.

This episode offers a grounded view on where AI delivers value today and how to apply it in ways that actually move the business forward.

In this episode, you’ll learn:

• Anticipate stakeholder needs with predictive plans - use past data to identify possible future requirements of a customer
• Concentrate on niche industry solutions - identify your skills and solve deep hurdles in that field
• Implement a curated response process for complaints - automating quick solutions for minor dissatisfaction

Things to listen for:
(00:00) Introduction

(00:51) What Wing does and why it matters now

(01:51) Using AI for personal performance and nutrition

(03:24) Wing’s early vision for AI and digital assistants

(05:20) How GPT accelerated productivity and workflows

(07:21) AI as augmentation, not replacement

(09:14) Implementing AI across a global workforce

(10:48) Anticipating customer needs with AI systems

(12:43) Why customer education drives AI success

(15:58) Advice for leaders starting their AI journey

(19:13) Lightning round and final thoughts

In this episode of The Unexpected Lever, Jarod Greene is joined by Jamie Walsh, Founder of GTM Factories, to pull back the curtain on how legacy incumbents can outmaneuver nimble startups. Jamie reveals the internal framework he used to dismantle a traditional 15-month product launch cycle and replace it with a high-velocity 90-day sprint.

Beyond the strategy, you'll hear the 'messy' side of AI implementation: the discipline required to stop tool-hopping every week and the importance of giving your team grace to experiment with agents. 

Whether you’re a product marketer tired of long roadmaps or a sales leader looking for automated competitive intelligence that actually works, Jamie’s 'always-on' systems provide the blueprint for the 2026 GTM engine.

In this episode, you’ll learn:

• Ship faster with shorter cycles - learn how to condense 15-month launches into 90 days
• Build always-on intelligence systems - use automation for competitive tracking and customer insights
• Avoid the tool switching trap - stick with a core platform for two quarters to see actual results 

Things to listen for:
(00:00) Introduction 

(00:56) Why incumbents must move faster

(02:14) Using AI for health goals and daily motivation 

(04:13) The danger of tool rabbit holes

(05:33) A 5-year vision for cognitive risk management and compliance 

(09:37) Reducing long launch cycles to a 90-day sprint 

(12:19) Giving your employees grace to experiment

(13:48) Simple ways to start your AI journey today 

(16:43) Why discovery calls are still an art and not a science 

(14:57) AI as a magic wand for frameworks

(16:29) Must-listen podcasts and books on AI

(17:48) Connecting with Jamie

In this episode of The Unexpected Lever, Jarod Greene sits down with Chad Sly, Vice President of Sales at Braintrust, to talk about what AI adoption actually looks like inside revenue teams. From using AI as a thinking partner for deep account research to diagnosing stalled deals,  they dig into why most AI rollouts fail, how old implementation playbooks break in a high-velocity AI world, and why adoption is a human challenge, not a training issue. Chad also breaks down practical wins, like automating admin work and improving pipeline hygiene, and the risks of treating AI as just another sales tool.

If you lead sellers or carry a quota yourself, this is a grounded look at how to move faster with AI without losing the human edge that closes deals.

In this episode, you’ll learn:

• AI as a thinking partner – use AI to pressure test ideas and sharpen deal strategy
• Adoption is a leadership challenge – change management matters more than training
• Automate admin, elevate sellers – offload CRM updates and research to focus on selling

Things to listen for:
(00:00) Introduction

(01:23) Most unexpected personal and professional uses of AI

(02:26) AI for deep account research and financial analysis

(04:30) Chad’s AI origin story and mindset shift

(06:21) Where teams start with AI: Efficiency and admin work

(07:29) Biggest barriers to AI adoption and implementation

(09:00) Top-down mandates vs. bottom-up AI experimentation

(11:10) Early AI wins with mini GPTs for account research

(12:09) Where AI still falls short in sales communication

(13:45) Advice for skeptics and how to get started with AI

(17:09) The sales process AI should automate next

(18:15) Resources, hype, and where to connect with Chad

In this episode of The Unexpected Lever, Jarod Greene sits down with Darren Brady, Vice President of Strategic Accounts at Corporate Visions, to discuss how AI is reshaping buyer expectations. With more data at every seller’s fingertips, buyers assume you know their business before the first call.

Darren explains why the appetite for human interaction is actually growing, what true personalization looks like now, and how sellers can meet higher expectations without losing authenticity.

In this episode, you’ll learn:

• Why AI increases buyer expectations – access to data means no excuse for generic outreach
• Personalization is the demand – surface insights that reflect the customer’s business
• Human connection still wins – AI supports preparation, not relationships

Things to listen for:
(00:00) Introduction

(01:09) The unexpected way AI was used to build a full business plan

(03:00) Darren’s AI origin story and the first scalable use case he saw

(04:21) Turning AI into a team-wide business case engine

(05:38) Why AI is raising the bar for seller business acumen

(07:54) When buyers use AI to reshape your business case

(09:30) The evolution of enablement in an AI-driven world

(11:44) The rise of the GTM engineer and AI skill enablement

(13:30) AI wins that scaled across teams

(17:37) AI missteps, broken automations, and rebuilding trust

(20:30) Build, buy, or wait? Navigating AI decisions in uncertain times

(23:13) Practical advice for getting started with AI today

(27:22) Pricing automation, revenue resources, and where to connect

In this episode of The Unexpected Lever, Jarod Greene sits down with Seth Marrs, Chief Strategy Officer at Sandler, to cut through the AI hype and focus on what actually moves revenue.

Seth shares why starting with value changes everything, how most teams are sequencing AI incorrectly, and why the real advantage is not speed, but quality.

In this episode, you’ll learn:

• Why value must come before tools – start with the outcome, then apply AI
• What hasn’t changed in go-to-market – strategy still drives results
• Where AI truly creates advantage – quality beats efficiency every time

Things to listen for:
(00:00) Introduction

(01:06) Why sellers spend more time preparing than selling

(01:47) Why AI matters right now for GTM teams

(02:48) Everyday AI use cases that build real fluency

(05:14) AI adoption is actually gaining traction

(08:59) Starting with business value, then applying AI with purpose

(10:55) AI is now delivering quality, not just efficiency

(11:52) Turning sales conversations into insights

(12:42) When AI becomes a shiny object instead of a growth lever

(14:54) Practical advice for operators ready to solve real problems

(15:26) Proving ROI in enablement and why AI is a true partner

In this episode of The Unexpected Lever, Jarod Greene is joined by Bill Balnave, Head of Customer Success at Mezmo. Bill has led post-sale, solutions, and customer teams through real AI adoption under real constraints.

Bill shares how necessity forced action, why trust slows teams down, and how leaders should rethink AI as part of their workforce.

In this episode, you’ll learn:

• Why trust breaks AI adoption – Teams hesitate when answers feel unproven
• Where AI creates leverage – Speed comes from removing manual context switching
• Why ownership matters for agents – Unclear roles lead to noise instead of impact

Things to listen for:
(00:00) Introduction
(00:55) How Mezmo helps teams make sense of data

(01:43) The most unexpected ways Bill uses AI

(02:27) What pushed AI from interest to action

(04:52) Why teams struggle to trust AI answers

(09:49) Rethinking AI agents as part of the team

(13:59) The risk of delaying AI adoption

In this episode, we discuss how sales teams are using AI without breaking what makes selling work. Jarod Greene sits down with Terence Falk, VP of Sales at 8am, to talk about pipeline generation, qualification, and the risks of over automating human work. Terence shares how his team uses AI to remove friction from research, routing, and prep while keeping judgment, communication, and emotional awareness firmly in the hands of sellers. 

You will hear why quality beats scale, where AI actually earns its keep, and why great sellers remain hard to replace. 

In this episode, you’ll learn:

• How AI fits into real sales workflows - Use tools to clear friction, not to run the sale
• Why small improvements beat full automation - Quality gains compound faster than blanket scale
• Which skills keep sellers relevant - Judgment, curiosity, and live conversations still decide outcomes

Things to listen for:

(00:00) Introduction

(01:38) Using AI without replacing sellers

(03:09) Trading scale for higher quality leads

(05:32) Where small AI wins actually add value

(07:24) AI for real time sales enablement

(08:47) The limits of AI in sales and law

(11:33) AI speeds things up but does not own quality

(14:49) How sales and marketing change with AI

Scott shares how leaders should think about AI in practical terms, where insight turns into action, and how to avoid overcomplicating adoption.

In this episode, you’ll learn:
Why focus matters in AI – Solving one problem beats chasing every use case
How insight becomes action – Data only works when it changes decisions
Where small wins add up – Early results build trust across teams

Things to listen for:
(00:00) Introduction
(01:16) What CBTS does and why it matters
(02:17) Unexpected AI use case
(03:37) The trigger moment for AI adoption
(06:46) Building AI adoption across teams
(10:19) Experimenting with AI while managing risk
(14:39) Advice for leaders getting started with AI
(16:07) Where AI is headed for sales planning and forecasting

Season 2 of The Unexpected Lever explores how sales leaders and technical teams are actually working alongside AI. Not the hype, not the theory, but the honest stories of what’s working, what’s not, and where human judgment still matters most.

Join us for real conversations with the people navigating AI inside sales teams. You’ll hear what they’re learning, what they’re rethinking, and how small shifts are changing how teams work and win together.

In this episode of V5, Jarod Greene, CMO at Vivun, explains why marketing should step away from slide creation and focus on owning the message. After two decades of building decks for every sales moment, Jarod realized the problem wasn’t about how decks looked or how long they were; it was about who controlled the story.

He discusses how giving reps ownership of the story, supported by strong positioning and AI-powered tools, creates faster, more effective conversations with buyers.

In this episode, you’ll learn:

• Why marketers should stop building decks – Ownership matters more than formatting
• How reps create stronger meetings – Let them shape the story, not recite slides
• Where enablement actually begins – Context drives conversions more than content ever will

Things to listen for:
(00:00) Introduction
(00:44) Why marketers need to stop making decks
(02:00) What marketing should actually own
(03:20) How letting go of control changed everything
(04:40) What reps really want from marketing
(05:22) The shift that makes enablement actually work

In this episode of V5, Jarod Greene sits down with Ryan Heinig, CRO at 2X, to talk about the fundamentals that separate top sellers from everyone else. Ryan discusses the four things every great seller does, and why mastering the basics is what drives consistent wins.

Ryan also explains the real role of sales enablement, the power of coaching within teams, and how community-driven relationships keep buyers engaged long before they enter a sales cycle.

In this episode, you’ll learn:

• What the best sellers focus on every day – The four fundamentals that drive results
• How leaders can enable better performance – Coaching, not content, creates impact
• Why community matters more than cold outreach – Relationships build lasting pipeline

Things to listen for:

(00:00) Introduction

(00:32) The four fundamentals that drive enterprise sales

(01:55) How AI helps sellers stay relevant, not robotic

(02:59) Why enablement starts with first-line leaders

(04:25) How community replaces cold outbound

In this episode of V5, Jarod Greene sits down with Em Daigle, Founder and Chief Automation Officer at OTTO-MATES, to discuss how to really build trust with buyers and how “value” has become a buzzword in sales, often used without any real connection to what customers actually care about.

Em explains why enablement misses the mark when it skips the human side of discovery, and shares how better questions (not just more of them) can completely change the trajectory of a deal. She also discusses where AI should step in and where it should step aside, especially when credibility is on the line.

If you're relying on process alone, you’re probably just presenting instead of truly selling.

In this episode, you’ll learn:

• Why trust earns attention – Value isn’t real until your buyer believes you 
• How to fix enablement – Teaching reps the buyer’s world is a game changer
• Where AI fits in – Use it to free up time, not replace your connection

Things to listen for: 

(00:00) Introduction

(00:29) Why “value” talk falls flat in sales

(01:50) How to truly earn buyer trust

(02:58) Fixing enablement with more profound discovery

(03:44) Where AI helps and where it hurts

On this episode of V5, Jarod Greene chats with Ann about why top-performing reps are rethinking how they prioritize accounts and spend their time.

Ann explains that selling today is more about spotting signals early, sometimes before buyers even realize a need exists. She discusses the role of predictive intelligence, why historical data is insufficient, and how modern sellers can minimize noise by acting on forward-looking patterns. With millions of companies to sort through, the differentiator is no longer effort but timing.

In this episode, you’ll learn:

• Why forecasting is a seller’s edge – Anticipating future need helps you win before competitors show up
• How to use predictive signals – Growth indicators and hiring trends can point to high-propensity buyers
• Where reps lose momentum – Spending time in the wrong places slows pipeline and kills deals before they start

Things to listen for:
(00:00) Introduction
(00:18) Forecasting is the underrated sales skill
(03:03) Crunchbase’s predictive growth signals explained
(04:06) Getting ahead of buyer needs without spooking them
(05:18) Balancing AI scale with human connection
(06:32) What AI can and can’t replace

In this episode of V5, we talk about why risk mitigation, not ROI, is what actually unlocks budgets and moves deals forward. Jarod Greene chats with Daryl Weldon, VP of Sales at Verisys, about why so many deals stall at the procurement stage and how to address this issue.

Daryl shares what sellers miss when they push growth over protection, and explains how compliance, legal, and brand concerns influence decisions long before signatures are signed. She lays out what it looks like to build a value case that speaks to multiple stakeholders, including those you may never meet. Her take: if your deal keeps stalling late in the cycle, it’s probably not a pricing issue.

Learn how to quantify inaction, tailor your pitch beyond growth, and leverage risk as your strongest sales tool.

In this episode, you’ll learn:

• Why risk builds urgency – Buyers don’t just want results, they want to stay out of trouble
• How to multithread smarter – Risk stories resonate with legal, finance, brand, and beyond
• What your deck might be missing – The cost of doing nothing is just as crucial as the upside

Things to listen for:
(00:00) Introduction
(00:33) Why ROI sounds like hope, not control
(01:20) How growth-first mindsets miss buyer pain
(02:36) What stalled deals reveal about your pitch
(03:17) Risk as a tool for multithreading

In this episode of V5, we look at why curiosity, not memorization, is the skill top sellers rely on to win today.

Jarod Greene sits down with Tim O’Neil, Chief Sales Officer at 6sense, to talk about how sales has evolved and why old habits are no longer effective. Tim explains how low-interest markets rewarded feature-heavy pitches, but today’s buyers expect reps to ask sharper questions, address real business pain, and connect with the right decision-makers. He also shares how he hires for curiosity and how AI is helping reps research smarter, not harder. 

If you’re stuck selling features, this is your wake-up call.

In this episode, you’ll learn:

• Why product knowledge isn’t enough – Knowing what your product does doesn’t mean knowing why it matters
• How curiosity shortens the cycle – The reps asking business-level questions are getting to the budget faster
• What to stop trusting – If someone only wants to talk about features, they’re probably not your buyer

Things to listen for: 

(00:00) Introduction

(00:20) Why product expertise no longer drives revenue

(01:28) Curious reps are closing with senior buyers

(02:18) Using AI to scale smarter selling

(03:41) Hiring reps who ask better questions

In this episode, Jarod Greene talks with Wendy Petty, CRO at WorkFusion, about the lost skill that still drives the biggest wins in sales: meeting face-to-face.

Wendy explains why sellers who rely on video calls are often leaving trust, nuance, and real connection on the table. She makes the case that younger reps, shaped by Zoom culture, need coaching to develop the in-person skills that build long-term connections. Her approach? Show up, in person, and lead by example.

In this episode, you’ll learn:

• Why face-to-face meetings close more – Selling is still about people
• How leaders can reset team habits – Start by modeling the behavior yourself
• What field selling unlocks – Faster trust, stronger signals, and more seats at the table

Things to listen for: 

(00:00) Introduction

(00:18) Why remote sellers lose enterprise deals

(02:05) Common excuses reps use to stay home

(03:34) What video calls miss about real selling

(04:10) The social skill every seller needs today

In this episode, Jarod Greene talks with Kate VanLue, VP of Revenue at AudiencePlus, about why she believes AEs should own the full journey from meeting booked to closed revenue.

Kate shares how the traditional SDR model has shifted into pure volume work that adds little value for sellers or prospects. She explains why compensation plans should reward AEs for carrying opportunities end-to-end, and how AI, events, and human connection are shaping better ways to create pipeline. Her perspective is clear: the future belongs to teams that replace high-volume outreach with real relationships and accountability.

In this episode, you’ll learn:

• Why the SDR role struggles to add value – High activity doesn’t always equal revenue
• What happens when AEs own meetings – Better conversion rates, stronger relationships, and cleaner incentives
• How teams can rethink pipeline generation – Use AI for signals, invest in events, and keep humans at the center

Things to listen for: 

(00:00) Introduction

(01:30) Why AEs outperform when sourcing their own deals

(03:04) Rethinking SDR roles and sales comp strategy

(04:40) Building enterprise sales talent without SDRs

(05:13) How AI changes go-to-market entry roles

(06:09) Why real human connection still matters

In this episode of V5, Jarod Greene sits down with Lindsay Rios, Fractional CRO of PowerChord, Inc., to question the logic behind experience-based executive hiring.

Lindsay challenges the assumption that startup success requires a leader who’s already taken a company from $10M to $50M ARR. She points out how this mindset leads to overpaying for familiarity while overlooking talented operators who already match the company's values, pace, and potential. Rather than chasing repeatable playbooks, she makes the case for finding someone ready to grow with the role, supported by coaching and context instead of inflated credentials.

In this episode, you’ll learn:

• Why experience can backfire – Hiring for logos can blind you to the real risks
• How to find the right fit – The best candidate might be the one who hasn’t done it yet
• What to prioritize in your next hire – Pay attention to adaptability, not just the resume

Things to listen for: 

(00:00) Introduction

(00:24) Why experience isn’t always worth the cost

(00:57) The myth of repeatable success

(01:56) How flashy hires distract from true fit

(03:23) What top talent actually wants today

(04:14) The real risk of past success bias

(05:38) Late bloomers often outperform early picks

That’s what Mike Head, CRO at PartnerStack, tells Jarod Greene in this episode of V5, as he shares his two bold takes on the future of sales teams.

Mike argues that AI is creating a wider gap between top sellers and everyone else. With prep work and research now outsourced to tools, many reps are starting to lean too hard on automation and skipping the fundamentals. This results in many people doing just enough to get by, but those who still put in the work pull even further ahead.

Mike also shares why AI could finally fix the long-strained relationship between sales and partnerships. If machines can surface the right partner at the right time and handle the busywork, there's no longer an excuse to go it alone.

In this episode, you’ll learn:

• Why average reps won’t survive – AI may replace the ones who aren’t adapting
• How AI changes partnerships – Automation can remove friction and boost deal size
• What separates top performers – Effort still matters, even in an AI-assisted world

Things to listen for: 

(00:00) Introduction

(00:23) AI will expose who’s actually prepared
(01:30) Sales tech doesn’t automatically mean better selling
(02:44) Why most reps will be replaced
(03:51) The new traits of top performers
(04:31) AI’s unexpected impact on partnerships
(06:28) Three practical steps to align sales and partners

In this episode, we explore how AI tools are changing outbound sales, and what separates average reps from great ones. Jarod Greene sits down with Austin Hitchcock, Senior Director of Account Development at Highspot, to discuss the future of pipeline generation, how AI is being misused by sales teams, and why human-first, creative outreach still wins. Learn how to build a high-output SDR team, avoid AI crutches, and drive pipeline in 2025.

In this episode, you’ll learn:

• Why AI makes average reps worse – Some treat it like a crutch, when it should be seen as a copilot
• How to build a high-output SDR team – Think ABM strategy, not task execution
• What separates good outreach from great – Personal video, smart research, and real human effort

Things to listen for: 

(00:00) Introduction

(00:43) Why pipeline is everyone’s responsibility now

(01:45) AI isn’t replacing reps,  it’s widening the gap

(02:32) What great reps do with AI tools

(03:45) Breaking through with real human outreach

(05:04) SDRs as ABM quarterbacks, not task robots

(07:26) Why in-person events still outperform digital efforts

On this episode of V5, Jarod Greene chops it up with Mark Niemiec, CRO at Salesloft, to unpack what sales is when you strip away the pipeline noise and pressure to close.

Mark believes a sale serves as proof that you helped a customer solve a priority business problem. He shares why discovery, creativity, and empathy matter more than pitch decks. He believes the best sellers operate like curious business thinkers. Mark also shares how an internal debate over using AI for sales research showed the tension between doing the hard work and moving faster. It eventually led to a new product launch, and it showcased that sellers who are earlier in their careers are quicker to embrace change.

In this episode, you’ll learn:

1. Why sales is the measurement, not the mission – Reps solve real problems or they don’t sell.
2. How AI became a POV-building engine – What started as an experiment turned into a product.
3. Where teams get stuck – Time wasted on research could be spent on creativity and strategy.

Things to listen for: 

(00:00) Introduction

(00:35) Redefining what sales is

(01:15) Traits of great problem-solvers in sales

(02:11) Should AI be allowed in discovery?

(02:45) Building a POV engine with AI

(03:37) Why AI adoption varies by background

(04:48) Early-career reps are leading the shift

In this episode of V5, Jarod Greene sits down with Todd Busler, CEO and co-founder of Champify, to question the certainty behind today’s loudest go-to-market opinions.

Todd sees a problem with the way leaders chase what’s trending, speaking in absolutes about which industries and approaches are 'dead,' without accounting for the complexity of different categories, motions, and stages of scale. He argues that most teams are too focused on cold outbound and not nearly focused enough on the rich first-party data already sitting in their CRM. From job changers to past champions, the real growth levers are often ignored.

In this episode, you’ll learn:

1. Why absolutes are misleading – Confident hot takes can distract from the nuance your business needs to succeed.
2. How first-party data unlocks scale – Former customers and closed-lost context can become your best revenue source.
3. Where your team might be wasting effort – Outbound isn’t dead, but it’s definitely harder. Knowing who already knows you is the better play.

Things to listen for: 

(00:00) Introduction

(00:40) Why talking in absolutes misleads teams

(01:18) Social algorithms reward bad advice

(02:27) Why Todd avoids comment wars

(02:59) Outbound is getting less effective

(03:53) Companies misuse first-party data

(04:28) Retention and brand now matter more

In this episode of V5, Jarod Greene is joined by Andrew Berger, VP of Revenue at Capchase, to challenge a long-standing sales tradition.

Andrew argues that quarterly and annual planning sessions waste more time than they’re worth. With countless hours spent on formatting, presenting, and guessing what will matter months from now, he believes the ROI just isn’t there. Instead, he’s pushing for a new approach that’s faster, more flexible, and powered by AI. By connecting systems and prompting smarter analysis, reps can spend less time preparing and more time selling.

In this episode, you’ll learn:

1. Why traditional planning slows teams down – Reps spend hours building plans that are outdated by the time they’re presented, creating more motion than momentum.
2. How AI can support better decisions – With connected systems and smart prompts, teams can surface relevant insights without digging through scattered data.
3. Where sales leaders can shift their focus – Moving away from rigid planning cycles opens up time to test, learn, and act on what’s actually working in the field.

Things to listen for: 

(00:00) Introduction

(00:24) Territory planning is broken

(01:11) AI changes sales strategy

(02:08) Presentations waste time

(03:01) Smarter account planning

(04:31) Speed over structure

(05:29) Building with new tools

In this episode, Jarod Greene chats with Kelley Hippler, CRO at Briefly, about why people-centered leadership is the key to building sales teams that last.

Kelley explains how CROs fall into the trap of managing up, missing what their team really needs. She talks about the pressure leaders feel from day one and how it pulls them away from trust-building and coaching. Her mission is simple: leadership should clear the path, not block it. That starts with getting real feedback, removing friction, and making space for reps to succeed on their own terms.

In this episode, you’ll learn:

1. Why top ICs often flop as managers – The best sellers don’t always make the best leaders.
2. How to spot leadership red flags early – Lack of trust, poor coaching, and misaligned priorities are just the start.
3. What people-first leadership looks like – Focus on enablement, not activity metrics, and keep the spotlight on your team.

Things to listen for: 

(00:00) Introduction

(00:41) The real reason CRO tenure is shrinking

(01:09) What people-centered leadership means

(02:11) Why new leaders obsess over managing up

(03:58) Advice for aspiring managers in sales

(05:11) How to remove friction for your team

(05:50) The mistake top reps make as managers

In this episode, Jarod Greene welcomes James Kaikis, CRXO at TestBox, to challenge how SaaS companies treat their customers after the deal closes.

James shares his frustration with buying software today, calling out the friction, the lack of follow-through, and the disappearing act many sales teams pull once a contract is signed. He makes the case that real value doesn’t come from the pitch but from what happens after. His fix? Rethink the roles we’ve boxed people into, especially Solutions Engineers and Account Executives, and bring their genuine expertise across the entire customer journey.

In this episode, you’ll learn:

1. Why trust breaks post-sale – Customers lose confidence when the people who earned their buy-in vanish at go-live.
2. How Solutions Engineers can drive value beyond the pitch – When SEs stay involved, buyers actually see what they were promised.
3. What sales teams should prioritize instead – Building credibility, sharing real proof, and sticking with the customer past the close.

Things to listen for: 

(00:00) Introduction

(00:36) Customers aren’t actually the priority

(01:08) Why buying software still sucks

(02:10) Building roles around buyer needs

(02:55) SEs hold untapped post-sale value

(03:53) Fixing the AE credibility problem

(04:33) Growth at all costs broke SaaS

In this episode, Vivun’s senior selling team, Account Executive Mike Capitolo and Sales Engineer Clay Killgore, join Vivun CEO Matt Darrow to reveal where most sales tools go wrong and what it looks like when AI is built with the rep in mind. 

They share how agentic AI helps cut prep time, eliminate Frankenstack bloat, and support strategic selling without getting in the way.

In this episode, you’ll learn:

1. Why most sales tech stacks are bloated – Clay shares how disconnected tools create drag and why simplifying your stack can lead to faster execution.
2. How agentic AI helps AEs sell more – Mike explains how AI can act on your behalf, handling tasks behind the scenes so you can focus on strategic conversations.
3. What useful AI workflows actually look like – Real-world examples of how intuitive, rep-friendly AI is replacing rigid systems and enabling real productivity.

Things to listen for: 

(00:00) Introduction

(02:25) How Large Language Models changed the way sellers learn

(05:34) Why agentic AI finally works for reps, not just managers

(06:33) Clutter from the old sales process

(07:33) Your AI as your copilot

(09:09) No more prompting: what agentic AI automates

(13:06) Scaling strategic selling without sacrificing quality

(19:53) Final takeaways: no more Frankenstack, no more guesswork

In this episode, Jarod Greene sits down with Lucas Welch, VP of Corporate Marketing at Highspot, for a conversation about authenticity, AI, and the power of personal connection in modern marketing.

Lucas shares how AI isn’t replacing relationships but encouraging deeper ones, especially when go-to-market teams build experiences that reflect what people actually care about. He walks through how his team uses tools like intent data and Mentimeter to shape events that feel personal, not prescriptive.

Tune in to get insight on how the next generation will treat AI as a co-pilot, and why staying curious is non-negotiable if you want to stay relevant.

In this episode, you’ll learn:

1. How AI is reshaping B2B relationships – Technology is forcing teams to create more intentional, human-first interactions that break through digital noise.
2. Why co-created experiences work – Gathering input before events leads to stronger engagement, better conversations, and more shared insights.
3. The importance of AI fluency in your career – As new sellers enter the workforce fluent in AI, the ability to learn and adapt is now a competitive advantage.

Things to listen for: 

(00:00) Introduction

(00:43) Why AI may lead to more human connection, not less

(02:07) Using intent data and surveys to shape high-impact events

(03:47) How co-creating agendas keeps people engaged and sharing

(05:18) Building trust with enterprise AI through secure adoption

(07:27) Why mastering AI now matters for future career relevance

(09:14) How authenticity fuels better collaboration and ideas

(13:39) Advice for junior marketers on asking, growing, and doing the work

In this episode, Vivun CEO Matt Darrow sits down with CMO and fellow podcast host Jarod Greene to discuss how marketing and sales teams can operate at a higher level using AI without losing the human element.

They share how a five-person marketing team can outperform teams four times its size, what gets in the way of broader AI adoption, and why the best enablement isn’t more training, but less friction. 

Human connection still closes deals. But the teams who move fastest with precision are the ones using AI to handle everything else.

In this episode, you’ll learn:

1. How AI helps lean teams scale up – Jarod breaks down the AI tools and workflows that power speed without sacrificing quality.
2. Why enablement needs a reset – It’s not about more content. You have to clear the clutter so reps can actually sell.
3. What’s slowing AI adoption – The blockers CMOs face and how teams are finding quick wins without waiting on perfect conditions.

Things to listen for: 

(00:00) Introduction

(02:14) Scaling faster without losing quality

(03:23) Breaking through the cold start problem

(05:00) Why some CMOs still stall on AI

(08:26) Rethinking SDRs with fewer tools, more output

(13:54) Enablement fails when content becomes noise

(19:13) Cutting through buyer fatigue with real value

(22:13) AI avatars can’t replace real relationships

In this episode, Jarod Greene sits down with Michelle Afshar, Global Head of Enablement at Darktrace, to unfold the shifting dynamics within B2B sales teams, focusing on the increasing importance of SEs.

Michelle explains why the future of sales belongs to sales engineers, emphasizing the need for sellers to be more technical. She argues that aligning SEs and AEs is essential for closing deals in today’s tech-driven landscape. 

Tune in to learn why modern sales roles are evolving.

In this episode, you’ll learn:

1. How sales roles are transforming – Michelle envisions a future where sales engineers are your best sales reps, adapting to the technical needs of modern buyers.
2. The challenges for AEs – Learn about the barriers organizations face in cultivating AEs with the technical prowess of an SE.
3. Redefining enablement – Discover Michelle’s strategy for equipping SEs with necessary sales skills, and AEs with necessary technical skills, emphasizing the importance of unified support across sales teams.

Things to listen for: 

(00:00) Introduction

(00:43) Successful sellers will be SEs

(02:36) The challenges of aligning AEs and SEs for better sales outcomes

(03:38) Understanding the modern buyer's journey and how it affects sales

(07:02) The role of enablement in supporting SEs

(09:50) The importance of training SEs beyond just product knowledge

(14:03) Strategies for structuring sales teams to foster collaboration

In this episode of V5, Jarod Greene sits down with Claudia Natasia, CEO of Riley AI, to discuss the evolving role of AI in customer insights.

Claudia breaks down how AI is transforming market research, but she’s quick to caution against a plug-and-play approach. Off-the-shelf tools or LLMs alone won’t cut it if you want a real edge. She shares why blending proprietary data with AI is the key to unlocking insights your competitors will miss. With Riley’s innovative approach, they're helping businesses uncover the kind of golden nuggets that actually move the needle.

In this episode, you’ll learn:

1. Why AI alone isn’t enough – To stay ahead, companies will have to use their own data alongside AI models to generate unique insights instead of blending into the field.
2. The value of proprietary data in gaining a competitive edge – Pulling from the same sources leaves you blind to opportunities others are missing.
3. How user research drives business success – Real customer stories not only shape product development but also fuel substantial revenue growth.

Things to listen for: 

(00:00) Introduction

(00:52) Using AI as a research tool

(02:00) The outdated GTM playbook

(01:47) Why AI tools fall short

(03:01) Riley AI’s data-driven approach

(04:27) User research’s business impact

In this episode, Jarod Greene connects with Kelly Lewis of  B2B Go-To-Market Strategy, to discuss the ever-evolving nature of the CRO role and B2B selling teams in general.

Kelly explains why today’s CROs need more than just sales skills. They have to master strategy, operations and even AI to lead teams effectively and scale success. She also predicts a rise in CRO educational programs to meet these needs.

Listen to learn how sales leaders can evolve into CROs and adapt to the growing expectations of this complex role.

In this episode, you’ll learn:

1. How the CRO role is expanding – Beyond sales, the role now includes responsibilities in operations and strategy, making it a more complex leadership position.
2. Why asking “why” matters – Sales leaders aspiring to be CROs must develop a deeper understanding of decision-making processes across their teams.
3. The shift towards a new breed of sellers – With AI transforming the industry, Kelly shares her thoughts on where the next generation of sales talent will come from.

Things to listen for: 

(00:00) Introduction

(02:25) Why scaling teams and adopting AI are key CRO challenges

(03:54) Balancing marketing, ops, and sales within the CRO role

(05:57) Why realistic expectations matter in revenue operations

(07:37) The role of behavior change in successful enablement

(13:09) How AI is reshaping the next generation of sellers

(14:17) The future of sales engineers transitioning to account executives

In this episode of V5, Jarod Greene talks with Margaret Kelsey, CMO of Kodaris, about the shifting landscape of B2B marketing.

Margaret argues that software has become a commodity—AI has made it easier than ever to build and replicate products. Yet many companies still rely on outdated go-to-market strategies instead of investing in brand and creative distribution. She explains why personal brands, employee advocacy, and strong cultural alignment are the key to standing out in a crowded market.

In this episode, you’ll learn:

1. Why traditional GTM playbooks don’t work – Relying on paid demand gen and performance marketing is no longer enough to win.
2. How brand has become the ultimate moat – When technology and distribution look the same, differentiation comes from the values and authenticity behind a company.
3. The power of advocacy at every level – From founders to employees, building trust through personal branding and cultural alignment drives long-term growth.

Things to listen for: 

(00:00) Introduction

(00:52) Software is now a commodity

(02:00) The outdated GTM playbook

(02:37) Why brand is the last competitive moat

(03:17) Leveraging podcasts for brand-building

(04:16) Personal brands and internal advocacy

(05:03) Hiring for cultural and brand alignment

(06:07) The flywheel that drives real growth

AI is changing the sales game, but are leaders truly harnessing its potential? In this episode, Vivun CEO Matt Darrow and CRO Trevor Jett break down what sales leaders need to know about AI agents.

From cutting through vendor noise to understanding the real impact on sales productivity, they bring clarity to an often-misunderstood topic. With firsthand insights from scaling high-performing teams, they explore how AI can democratize expertise, not replace sales roles.

Deal velocity and quality relationships don’t have to be at odds in B2B. Listen in to learn how leading teams are bringing more power to sales with Agentic AI.

In this episode, you’ll learn:

1. What makes an AI agent different – Why most sales leaders get the definition wrong and how it impacts decision-making.
2. Avoiding AI tool overload – How to filter out distractions and focus on tech that truly moves the needle.
3. Rethinking enablement – Why top reps don’t rely on traditional training and how AI can level the playing field.

Things to listen for: 

(00:00) Introduction

(01:08) How CROs navigate AI vendor pitches

(02:45) Defining AI agents: What most sales leaders get wrong

(04:13) The real challenge of AI tool sprawl in sales

(06:14) The spectrum of AI experiences: three AI categories every sales leader should know

(08:47) Too much “AI,” not enough actual intelligence 

(12:00) Agentic AI’s role in accelerating sales enablement and ramp time

(17:19) The myth of AI agents replacing sales teams

In this episode, Jarod Greene connects with Tom Josephson, Senior Director of Solution Consulting at TCP Software, to explore the power of discovery in building solid relationships with buyers.

Tom explains why curiosity is a superpower for SEs, how the right questions reveal real customer needs, and why great SEs show less, not more.

This episode gets into how SEs can shift their approach from demonstrating technical prowess to being strategic partners who understand the customer's goals.

In this episode, you’ll learn:

1. Why curiosity is essential in discovery – the best SEs ask insightful questions to uncover what truly matters to the customer.
2. When less is more in a customer conversation – Saying “yes” and moving on can be more effective than over-explaining, and a well-placed “no” can actually build credibility.
3. How to keep prospects engaged – Letting them feel like they’re driving the conversation creates stronger buy-in and more powerful rapport. 

Things to listen for: 

(00:00) – Introduction

(00:54) – Why curiosity makes discovery more effective

(02:25) – Why SCs should resist the urge to show everything

(03:54) – When to say “yes” and move on (and when to ask follow-ups)

(05:57) – The power of a well-placed “no” in sales conversations

(07:37) – Helping prospects reframe the problem, not just the solution

(14:17) – How great SCs shift from demoing features to guiding decisions

In this special V15 episode, Jarod Greene sits down with Marjorie Abdelkrime, Head of US West and Healthcare Solutions at VMware by Broadcom, to explore what separates great SEs from those who get stuck. Marjorie shares why curiosity is the most critical trait for success, how Sales Engineers can build trust by admitting what they don’t know, and why AI-powered demos provide an opportunity to elevate the human element in technical sales. She unpacks the evolution of the SE role, from product expert to strategic advisor, and the mindset shifts required to elevate sales engineering conversations.

From leveraging AI to enhance—not replace—SEs to understanding the customer’s customer, this episode explores the nuances of modern solution consulting.

In this episode, you’ll learn:

1. Why curiosity is the foundation of SE success - The best SEs go beyond technical expertise by asking deeper questions, uncovering business needs, and connecting solutions to real customer challenges.
2. How admitting “I don’t know” strengthens credibility - SEs who acknowledge knowledge gaps and follow up with thoughtful insights build stronger trust with customers and internal teams.
3. The evolving role of AI in sales engineering - AI-powered demos can enhance efficiency, but SEs need to double down on soft skill development to drive meaningful business conversations and strategic decision-making.

Things to listen for: 

(00:00) Introduction

(00:58) Why curiosity determines SE success

(02:25) The danger of pretending to know it all

(03:54) AI’s role in demos and what it can’t replace

(05:57) How SEs can use AI to advance their careers

(07:37) Understanding the customer’s customer

(14:17) From demo expert to trusted business advisor

In this episode of V5, Jarod Greene welcomes Jeff Margolese, SVP of Global Solution Consulting at ServiceNow, to break down one of the biggest challenges in B2B SaaS: showing real customer value. Jeff shares why sales teams often get caught up in showcasing features without connecting them to business impact—and how to fix it. He explains the power of storytelling, why ‘before and after’ framing is crucial, and how differentiation is more important than ever in a crowded AI market.

From improving sales conversations to sharpening presales strategy, this episode explores the mindset shifts that drive better outcomes.

In this episode, you’ll learn:

1. Value-driven sales methodology changes the game – The best SEs don’t just showcase features; they frame solutions in the context of a buyer’s real challenges, making the “before and after” crystal clear.
2. The qualities of the best SC to ever live – The most effective Solution Consultants embrace curiosity—not just about the tech, but about their buyers as people. From noticing what books are on their desks to asking the right questions, curiosity is the key to differentiation.
3. How to connect features to business outcomes – Buyers want to see the cool tech, but what they really need is to know what’s in it for them. Aligning demos with real-world impact ensures your solution doesn’t just look good—it makes sense.

Things to listen for: 

(00:00) Introduction

(00:32) The challenge of showing true customer value

(01:15) Balancing demos with customer relevance

(02:36) The power of storytelling in sales

(03:32) Differentiation in an AI-saturated market

(04:30) Curiosity as a key trait in solution consulting

Agentic AI is poised to transform B2B, but will security concerns block its potential? In this episode of The Unexpected Lever, Vivun CEO Matt Darrow sits down with security leaders Jamie Brown and Jessica Siclari to separate fact from fear in AI Agent security.

From navigating the evolving threat and regulatory landscape to designing a framework for AI vendor evaluations, they cut through the hype and provide a practical lens into how businesses can embrace AI Agents without compromising security.

In this episode, you’ll learn:

1.  The actual risks of AI agents – Beyond the buzzwords, what threats actually matter? From data training risks to AI hallucinations, and which security principles remain unchanged?
2. How to navigate shifting regulations – What global businesses must know about compliance in the U.S., EU, and beyond.
3. Red flags when evaluating AI vendors – The non-negotiables for keeping your data protected.

Security and innovation don’t have to be at odds. Listen in to learn how leading security teams are safeguarding data—while still embracing the power of Agentic AI.

Things to listen for: 

(00:00) Introduction

(02:15) AI’s impact on security and risk management

(04:46) The hidden risks of AI model training

(07:15) Data loss: the security team’s worst nightmare

(09:22) AI regulations: the U.S. vs. the EU

(11:34) Red flags when evaluating AI vendors

(13:26) The key to AI security: adaptation, not avoidance

In this episode of V5, Jarod Greene sits down with Toby Penn, an experienced global presales leader, to explore how AI agents are transforming sales engineering. Toby shares how AI, specifically Vivun’s AI Sales Engineer, Ava, is helping presales teams ramp faster, stay ahead of process changes, and focus on high-value tasks. He discusses the role of AI in simplifying sales enablement, fielding complex technical questions, and even empowering Account Executives with better decision-making. 

From scaling SE expertise to improving sales rep independence, this conversation highlights how AI agents are reshaping the go-to-market landscape.

In this episode, you’ll learn:

1. How an AI SE accelerates onboarding – Cutting PreSales ramp time from months to weeks by providing real-time guidance and training.
2. The difference between knowledge and expertise in AI agents - The best AI solutions don’t just retrieve knowledge. They have the expertise to present information in the context you need for real-world success.
3. How an AI Sales Engineer increases sales efficiency – Freeing up SEs from repetitive tasks and enabling AEs to make smarter, data-driven decisions, without distracting SEs from value-driven work.

Things to listen for: 

(00:00) Introduction

(00:22) AI and presales enablement

(01:31) Reducing sales onboarding time with AI

(02:53) AI’s role in continuous sales enablement 

(03:41) Extending AI beyond presales

(04:45) The importance of domain expertise in AI agents

(05:37) AI for sales independence and scale

In this episode of The Unexpected Lever, Jarod Greene sits down with Mark Kilens, CEO and Co-Founder of TACK, to challenge a long-held belief in B2B marketing. 

Mark argues that traditional channels—email, paid ads, and SEO—are losing effectiveness while networks are becoming the real drivers of growth. He breaks down the shift from channels to networks and why companies need to rethink their marketing strategy. From building a network map to understanding the power of trust, this conversation explores a new way to connect with buyers.

In this episode, you’ll learn:

1. Why traditional channels are losing impact – High costs, crowded spaces, and diminishing returns are making old-school marketing tactics less effective.
2. How networks are shaping modern marketing – People, brands, and places hold more influence than ever, and leveraging them is key to growth.
3. The role of trust in reaching buyers – Aligning with trusted figures, communities, and brands can build credibility faster than any paid campaign.

Things to listen for: 

(00:00) Introduction

(00:25) Channels are dead—sort of

(00:56) The challenge with traditional channels

(01:36) The power of networks over channeling

(02:22) Rethinking marketing plans and budgets

(03:40) Building a network map
(04:37) Trust: the foundation of successful networks

In this episode, Jarod Greene welcomes back Bill Balnave, Vice President of Technical Services of Mezmo, to explore how outdated sales processes are creating unnecessary friction for buyers and sellers alike. Bill shares why software should sell itself and how empowering buyers with the right tools and information can revolutionize the industry. From the evolving role of SDRs to cutting out red tape in SaaS deals, this conversation dives into bold ideas for a frictionless future.

In this episode, you’ll learn:

1. The real role of sales reps in a modern world: Traditional SDR and sales rep models are losing relevance. Instead, SEs and customer success teams are becoming the real value drivers.
2. Eliminating friction in SaaS buying: Transparent pricing, simplified contracts, and intuitive onboarding are powerful in creating seamless customer experiences.
3. Why software should sell itself: Enable prospects to explore, test, and understand products independently. It changes the game for vendors and buyers alike when you can let the product speak for itself.

Things to listen for: 

(00:00) Introduction

(00:30) Why SaaS sales processes are broken

(01:47) Addressing misconceptions about technical buyers

(02:20) Simplifying contracts and eliminating redlines

(03:17) Transparent pricing and flat rates for customers

(04:03) The limitations of SDRs in modern SaaS sales

(04:48) The shift to SEs and customer success teams

(05:24) How self-service and digital tools empower buyers

(05:44) Open-source solutions as a low-friction alternative

(06:36) The generational shift required for sales streamlining

(07:17) The evolution of the sales rep’s role in SaaS

In this episode, Vivun CEO Matt Darrow talks with Vivun’s Lead AI Product Designer, Stephany Cardet, about what goes into designing AI Sales Assistants that don’t just follow your lead—they help you stay ahead.

Stephany shares how Vivun’s tool Ava takes the guesswork out of the process—anticipating next steps, simplifying complex tasks, and making collaboration natural. 

Learn how smarter design can help you do your best work, every time.

In this episode, you’ll learn:

1. From Buttons to Brilliance: How design is shifting from rigid SaaS interfaces to agentic AI, where conversational design empowers users.
2. Trusting the Unknown: The human barriers to AI adoption—and how proactive, personalized agents like Ava build trust and reduce ambiguity.
3. More Than a Shell: Why AI agents don’t need traditional UIs and how Ava’s intelligence adapts to your unique style, even knowing what she doesn’t know.

Things to listen for:
(00:00) What agentic AI is and how it’s reshaping work
(00:15) Meet Stephany Cardet
(00:32) Why human-centered design is key to better sales tools
(01:02) How thoughtful design makes tools feel intuitive
(04:00) The shift from rigid interfaces to dynamic, conversational tools
(06:30) How proactive tools simplify workflows and save time
(09:10) Building trust with tools that explain their actions
(12:00) Smarter tools that eliminate silos and foster teamwork
(15:30) What makes AI feel like a trusted teammate

In this episode, Jarod Greene sits down with Nicole Kawamoto, Director of Solutions Engineering from ServiceTitan, to explore how a shift in quota strategy can transform team dynamics and drive performance. Nicole shares why she moved her Solutions Engineering team to a hybrid quota model, the surprising impact it had on morale, and how it aligns SEs and AEs to crush sales goals together. 

In this episode, you’ll learn:

1. Why individual quotas matter for SE teams: Introducing a hybrid quota model boosts performance, aligns SEs and AEs, and keeps everyone striving toward shared sales goals.
2. The impact of team alignment on morale and results: Blending individual and team-based metrics fosters collaboration without sacrificing motivation or financial incentives.
3. How quotas drive career satisfaction: Hear Nicole's approach to using quotas as a tool for retaining top talent and creating long-term career satisfaction within the Solutions Engineering role.

Resources:

Job openings at ServiceTitan: https://www.servicetitan.com/job-openings

Things to listen for: 

(00:00) Introduction

(01:06) The initial team-based quota model and its benefits

(01:53) Challenges with team-based quotas and the need for change

(02:38) Transitioning to a hybrid quota model

(03:36) Improved morale, financial gain, and team alignment

(04:11) Maintaining a collaborative team culture with individual accountability

(05:05) The value of the hybrid quota model

In this episode, Jarod Greene sits down with Dave Greene, Regional Vice President of Solution Consulting at Gainsight, to unpack why the days of multi-product generalists are fading fast. Dave explains why buyers demand deeper expertise from SCs and how specialization is driving better outcomes for both customers and teams.

In this episode, you’ll learn:

• Why specialization is the future of solution consulting: Dave explains why the shift away from multi-product generalists is critical to meeting buyer expectations and delivering deeper, more effective support.
• How to address burnout in solution consulting teams: Teams managing multiple product lines and geographies can improve performance and morale by prioritizing specialization.
• The evolving role of SCs in customer success: Solution consultants are uniquely positioned to support customers both pre and post-sale because of their technical training.

Things to listen for:

(00:00) Introduction
(00:21) Why multi-product generalists are becoming obsolete
(00:48) The value of specialization in solution consulting
(01:27) Addressing SC burnout and challenges with multiple product lines
(01:53) Why buyers want deeper expertise and customized solutions
(02:31) The critical role of SCs in pre- and post-sales collaboration
(03:43) The synergy between SCs and CSMs for customer outcomes

In this episode, Jarod Greene chats with Russell Witham from Vivun, to unpack how AI is reshaping your interactions with vendors and customers. From near-human digital assistants to AI systems that can tackle the unexpected, Russell shares his take on why the next few years could redefine the way we work and communicate.

In this episode, you’ll learn:

1. The future of AI-driven customer interactions: Why AI-powered tools are poised to blur the line between human and machine in customer support and beyond, transforming how businesses engage with clients, partners, and vendors.
2. Breaking free from rigid decision trees: Advanced AI agents can handle edge cases and complex scenarios. This will help customer service systems be more agile and will eliminate the frustrations of traditional, structured support systems.
3. AI's growing role in B2B SaaS: We all know the evolution of AI technology is accelerating. This means we have to create solutions that adapt and respond just as fast. Businesses have the opportunity to harness AI tools to improve workflows and customer experiences, and maintain a competitive edge.

Things to listen for: 

(00:00) Introduction

(00:21) The rise of AI in B2B SaaS

(01:29) The Turing Test and its relevance to modern AI

(02:28) How AI is expanding beyond structured decision trees

(03:03) Why today’s AI tools are better equipped to handle edge cases

(03:25) The evolution of AI capabilities and what’s coming next

(04:39) Why now is the time to embrace AI-driven solutions

In this episode, Jarod Greene sits down with Dave Schultz, Head of Solution Consulting at Employ, to explore how flexibility and adaptability are transforming the SE role. From navigating unpredictable buyer behavior to leading with empathy in new leadership roles, Dave shares his insights on building agile teams and creating impactful strategies that align with the shifting needs of modern B2B sales.

In this episode, you’ll learn:

1. Evolving the SE Role: The Sales Engineering/Solution Consultant role is shifting. It requires flexibility and adaptability to meet buyers where they are, even if it means stepping outside traditional processes.
2. Key Skills for Modern SEs: Communication, agility, and handling curveballs are essential traits for SEs navigating unpredictable buyer behavior and complex sales environments.
3. Leading With Empathy: Dave shares his approach to leadership in new roles, emphasizing thoughtful decision-making, cross-functional collaboration, and building trust within teams.
4. Adapting to Buyer Behavior: Today’s buyers approach purchasing decisions differently. This means SEs have to stay ahead by tailoring their strategies to address these changing dynamics.

Things to listen for: 

(00:00) Introduction

(00:18) The changing landscape of the SE role 

(01:10) Dave’s thoughts on disco demos

(02:04) Adapting to unpredictable buyers 

(02:50) Essential skills for modern SE

(03:21) Why talk tracks work better than scripts 

(04:25) Dave’s first 30-60-90 days and his approach to leadership

(05:13) Preparing for long-term success in 2025

In this episode, Jarod Greene sits down with Julia Lustig, Head of Sales Engineering for Southern Europe at Seismic, to discuss what sales teams need to be thinking about. With budgets tighter than ever, Julia shares how to make data-informed decisions, foster collaboration, and stay flexible while maintaining focus. 

You’ll discover why small, intentional changes can drive big results and how aligning your team around a shared mission sets the stage for success.

In this episode, you’ll learn:

1. The Power of Purposeful Planning: Being intentional with your strategy can help teams navigate tight budgets, limited resources, and changing markets.
2. Data-Driven Decision Making: Analyzing patterns and structuring feedback from clients and prospects can guide teams toward focused and impactful actions.
3. The Importance of Collaboration: Fostering a collaborative environment helps teams align around a shared mission while avoiding scope creep and chaos.
4. Small Steps, Big Results: Breaking down challenges into manageable actions can lead to meaningful progress and sustainable success.

Things to listen for: 

(00:00) Introduction

(00:42) Why businesses must embrace purposeful planning

(01:28) Using data to focus on what works and avoid chaos

(02:26) Collaboration and structured feedback in decision-making

(03:18) How small, intentional changes lead to long-term success

(04:06) Balancing flexibility and commitment in team strategies

(05:00) Julia’s advice on mental health and speaking up

In this episode, Vivun CEO Matt Darrow talks to Senior Sales Engineer Taylor Bukowski about the evolving role of AI in sales engineering.

As an early adopter of generative AI and Vivun’s AI Sales Engineer in particular, Taylor shares her firsthand experience using it to level up her workflow, career, and customers’ experiences. All without replacing the human touch that makes SEs irreplaceable.

Tune in to learn how to use AI not as a replacement but as a partner in your SE success.

In this episode, you’ll learn:

1. Leveraging AI for Strategic Advantage: AI tools, like Vivun’s AI SE, Ava, can streamline everyday SE tasks. They boost productivity and allow you to focus on high-impact work like relationship-building.
2. Think About AI Like a Teammate: As AI continues to evolve, stay curious and adapt to new tools that will keep you ahead of the curve. AI isn’t here to replace you. It’s here to enhance your abilities.
3. AI for Efficient Knowledge Sharing: AI helps spread knowledge across teams, giving everyone access to valuable insights and preventing information silos.

Things to listen for:
(00:00) Why AI is a valuable tool for SEs

(03:12) Debunking the myth that SEs only do demos

(06:29) How Taylor leverages AI to free up time for relationship-building

(09:08) Using AI for demo scripts and tailoring them to personal style

(11:25) How AI helps organize complex customer needs

(14:33) How AI keeps track of deals and updates in real-time

(16:48) The challenges of customer handoffs and how AI ensures continuity

(19:01) Spreading tribal knowledge across teams with AI

(21:05) How AI provides a self-service model for the sales team

(23:10) AI’s role in supporting the sales team

(25:01) AI is here to stay—don’t get left behind

In this episode, Jarod Greene chats with Kyle Coleman, CMO of Copy.ai, to break down the hype around prompt engineering and uncover how AI can deliver real value to sales and marketing teams. Kyle shares why teaching your team to write perfect prompts might be a waste of time and how the best AI solutions simplify the process for seamless integration.

In this episode, you’ll learn:

1. Why Prompt Engineering Is Overrated: Kyle explains why expecting your team to master complex prompting skills can lead to disappointment and why the best AI solutions remove the need for it entirely.
2. Smarter AI Adoption: Focus on tools that better integrate into your existing workflows. It will help you achieve sustainable results without overwhelming your team.
3. How to Balance AI and Human Connection: Automating everything isn’t the answer. Instead, use AI with the manual tasks to free up your people to do what they do best and ensure that your buyers still feel connected to your brand.

Things to listen for:

(00:00) Introduction
(00:18) Learning prompt engineering is a waste of time
(01:33) The best AI tools eliminate the need for complex prompts
(02:10) Common frustrations with AI 
(02:36) How AI can collapse time to insight and execution in sales
(03:20) Practical examples of AI transforming go-to-market strategies
(04:00) Balancing AI automation with human connection
(04:57) AI SDRs role in lead processing
(05:33) Leveraging AI tools effectively

In this episode,  Jarod Greene chats with Marjorie Abdelkrime, Head of US West and Healthcare Solutions at Broadcom, to unpack the many pathways into the Sales Engineering career. From breaking into the field to thriving in a highly technical industry, Marjorie shares her unconventional journey and offers practical advice for leveling up your SE career.

In this episode, you’ll learn:

1. Breaking Industry Stigma: Marjorie challenges the traditional view of SE roles. Varied career experiences—from IT to project management—can be the perfect launchpad for the role. There is no perfect background.
2. Essential Skills for an SE: Everyday tasks like managing stakeholders and positioning projects build critical selling and technical skills necessary for excelling in an SE role.
3. How to Level Up Your SE Career: If you want to grow as an SE, start with understanding your customers’ businesses, mastering the ecosystem around your solutions, and staying sharp with evolving technologies.

Things to listen for: 

(00:00) Introduction

(00:27) Why career progression for SEs is top of mind

(01:02) Marjorie’s unconventional journey into solution engineering

(01:47) How overcoming stigmas opens doors for aspiring SEs

(02:37) Why everyday skills are essential

(03:15) How to build confidence in transferable skills

(03:50) How understanding customer ecosystems enhances your impact

(04:09) The key to leveling up: staying sharp and thinking holistically

In this episode, Jarod Greene sits down with Zach Miller, CRO of VanillaSoft, about the real challenges of creating an enterprise sales strategy without disrupting a successful SMB pipeline. Zach shares the hurdles of transitioning to long-cycle, multi-stage deals and the importance of surrounding yourself with the right team.

In this episode, you’ll learn:

1. Building an Enterprise Sales Motion from Scratch: Establishing an enterprise sales motion requires careful planning to maintain an existing SMB pipeline, balancing new processes with proven success in smaller markets.
2. The Power of Team Alignment: Having the right people with clear objectives allows for efficient scaling and helps tackle challenges as they arise.
3. Challenges of Long Sales Cycles: Staying focused on core priorities is essential to managing the complexity of multi-stage deals without being overwhelmed by details.
4. Filling Knowledge Gaps as a CRO: Broadening expertise beyond traditional sales, especially in marketing and SDR functions, can be crucial for a CRO stepping into an enterprise role.

Things to listen for:
(00:00) Zach Miller’s hot take on building an enterprise sales motion

(00:28) The challenge of balancing enterprise and SMB sales

(01:15) Tackling the hurdles of starting an outbound motion from scratch

(02:15) Keeping priorities straight while adapting to a constantly changing sales landscape

(02:41) The importance of team alignment and focusing on key outcomes

(04:07) Advice for first-time CROs on filling knowledge gaps beyond traditional sales

In this episode, CEO Matt Darrow sits down with Vivun’s Sr. Machine Learning Engineer, Chen Liang, to explore why most AI just isn’t cut out for sales engineering—yet.

While language models like ChatGPT are powerful, they lack the insider knowledge and finesse that make sales engineers irreplaceable. Matt and Chen dive into Vivun’s unique approach to building AI agents that don’t just predict answers but deliver reliable, actionable insights grounded in real-world experience.

Discover how structured knowledge framework and top-down procedural graph prevent AI hallucinations and keep AI agents aligned with SE needs.

In this episode, you’ll learn:

1. Structured Knowledge for Smarter AI: Crafting a reliable AI system begins with a structured approach to knowledge, ensuring AI agents operate with accuracy and industry insight.
2. Preventing AI Hallucinations: Large language models often generate misleading responses, but with domain-specific guidance, AI can deliver more trustworthy results.
3. Real-Time Improvement Through User Feedback: Tracking user interactions, like the “frustration index,” helps AI continuously evolve and meet real-world demands.
4. AI as a Collaborative Team Player: Rather than just a tool, AI can become a partner in sales engineering, supporting complex decision-making with structured, actionable insights.

Things to listen for:
(00:00) Why AI alone isn’t enough for sales engineering

(05:09) How structured knowledge reduces AI hallucinations

(07:44) Using a knowledge graph to keep AI on track

(10:28) The importance of evaluation for AI reliability

(13:25) Real-world examples of AI’s limitations without domain knowledge

(15:23) Quantitative vs. qualitative methods for AI evaluation

(16:36) Real-time feedback and the “frustration index”

(18:46) Human-in-the-loop and automated quality checks

(20:05) Enhancing AI with ongoing data and real-time adjustments

In this episode, Jarod Greene sits down with Blue Bowen, Research Principal at G2, to explore the game-changing role of AI SDRs in inbound lead management. AI is reshaping the buyer experience, and if companies shift focus to inbound leads, it can provide immediate wins. Tune in to learn how companies can leverage AI tools to drive more meaningful connections with potential customers.

In this episode, you’ll learn:

1. How AI SDRs Can Enhance the Buyer Experience: Using AI-powered SDRs for inbound leads can streamline engagement, providing a timely, tailored experience for buyers, which boosts buyer enablement and ultimately drives success in a competitive market.
2. Balance AI and Human Interaction: For companies hesitant to adopt AI, Blue suggests starting with AI as a supportive tool rather than a replacement. This helps nurture and enrich inbound leads while maintaining a human touch.
3. Speed in Engagement Matters: Prompt responses are key—delays can push prospects toward competitors. AI SDRs can improve the chances of winning deals by responding swiftly and effectively.

For additional insights on 2025 Sales Trends, see Blue’s research in this G2 post.

Things to listen for: 

(00:00) Introduction

(00:27) Why inbound leads are the key focus for AI SDRs

(01:00) Differentiating between autonomous AI and co-piloting in sales

(01:31) The importance of nailing the basics for inbound lead management

(01:53) How AI SDRs can improve inbound processes

(02:36) The rise of AI tools and their impact on sales productivity

(03:15) How the buyer experience drives sales success

(03:52) Why timely responses and effective communication matters

In this episode, Jarod Greene sits down with Mark Huber, VP of Marketing at UserEvidence, as he shares his candid thoughts on the frustration of hidden pricing in B2B SaaS. He unpacks why transparent pricing is needed to build trust with buyers and how outdated sales tactics waste time for both teams and customers.

In this episode, you’ll learn:

1. The Importance of Price Transparency: Openly sharing your pricing can build trust with buyers and lead to faster decision-making.
2. Avoid Time-Wasting Sales Tactics: Hidden pricing can frustrate potential customers and waste valuable time for both your sales team and prospects.
3. Weed Out the Wrong Leads Early: Transparent pricing helps qualify leads from the start, saving your team from chasing prospects who can’t afford your product.

Things to listen for:

(00:00) Missing pricing information on pricing pages

(01:15) The impact of hidden pricing on the buyer's journey

(01:53) Inefficient demo calls without pricing transparency

(02:25) Weeding out unqualified leads through transparent pricing

(03:49) Why signal-based selling practices are absurd

In this episode, CEO Matt Darrow speaks with Vivun’s Product & AI Leader, Russell Witham, about the criteria for AI that actually “gets” sales engineering. 

Most existing models fail to appreciate the complexity and true value of SE work, resulting in outputs that fall short of what great sales engineers produce. 

Tune in to discover a new, innovative approach to empowering sales engineers with AI that understands them. 

In this episode, you’ll learn:

1. The Essence of Sales Engineering: The core role of a sales engineer lies in crafting tailored solutions that address customer needs rather than simply answering product questions or filling out RFPs. 
2. The Limitations of Current AI Models: While AI and large language models are gaining traction, they often lack the nuanced understanding required for effective sales engineering. Successful integration of AI requires structured data and a top-down approach to fully leverage its potential in sales processes.
3. The Four Core Benefits AI for PreSales: By focusing on the 60% of what SEs do, AI can free SEs from administrative burdens, collapse enablement times, improve agility to pursue new target markets, and increase operational efficiency.

Things to listen for:

(00:00) How companies are using AI in sales engineering
(04:42) The essence of a sales engineer's role
(08:48) Why Claude & ChatGPT isn’t good enough
(10:03) The importance of structured data for effective solutions in sales engineering
(11:53) The need for detailed knowledge representation in AI applications
(15:46) Why current AI approaches fall short for sales engineering

In this episode, Jarod Greene sits down with Kyle Smith, Managing Partner at The Bridge Group, to discuss the impact of direct alignment between sales engineers and account executives on customer experiences. Kyle shares his insights from the Sales perspective on how avoiding pooled resources can lead to smoother interactions and stronger client relationships.

In this episode, you’ll learn:

1. The Dangers of Resource Pooling: Kyle explains why pooling sales engineers can create a disconnect in the sales process and how it can lead to a less personalized customer experience.
2. Enhancing AE-SE Collaboration: Fostering effective partnerships between account executives and sales engineers ensures seamless communication and efficiency.
3. The Importance of Customized Demos: Learn how a well-prepared and targeted demo can address customer pain points, ultimately leading to higher conversion rates.

Things to listen for:

(00:00) The value of direct alignment in sales
(00:35) Why pooled resources can create unnecessary challenges
(01:50) Best practices for AE-SE collaboration
(02:45) The role of preparation in customer interactions
(03:30) How personalized demos enhance the buyer's journey
(04:15) Navigating organizational complexities in sales

In this episode, Jarod Greene sits down with Natalie Marcotullio, Head of Growth  and Operations at Navattic, as she shares about the pitfalls of traditional sales approaches, the importance of empowering buyers with the information they need, and how shifting our mindset can lead to stronger, more effective sales relationships.

In this episode, you’ll learn:

1. Trust Your Buyers: Buyers often have a deeper understanding of their own problems than sales representatives do about the product. Respect and leverage buyer insights to your advantage.
2. Rethink Sales Interactions: BDRs should lead meaningful discussions about buyers' challenges and goals, enabling AEs to offer tailored solutions for more productive engagements.
3. Empower Buyers with Information: Instead of gatekeeping information, give buyers the resources they need to qualify themselves.

Things to listen for:

(00:00) B2B sales process should focus on the buyers, not on sales reps
(01:10) Why BDRs might not be the best first interaction
(02:42) How demo automation has enhanced buyer journeys at Navattic
(03:04) Advice for CROs resistant to sharing information early
(04:22) Research report on the buyer-friendliness of Top 100 SaaS companies

In this episode, Jarod Greene sits down with Leah McTiernan, Global Vice President of PreSales at Docusign, as she shares her perspective on how AI is streamlining workflows, boosting team morale, and enabling more meaningful, strategic work. Learn how AI is enhancing the PreSales role to build stronger customer relationships and deliver greater value.

In this episode, you’ll learn:

• How AI Transforms PreSales Efficiency: Leah explains how AI automates time-consuming tasks like demo creation and research, allowing PreSales teams to focus on more strategic activities like consultative selling and personalized customer engagements.
• The Role of AI in Boosting Morale and Innovation: Discover how AI integration improves workflows and enhances team morale by fostering innovation, leading to more excitement and engagement within the team.
• Why AI Enhances, Not Replaces, PreSales Roles: Leah addresses the common concern of AI replacing jobs, showing how AI complements PreSales by allowing professionals to spend more time on meaningful, strategic work, making their roles more valuable and fulfilling.

Things to listen for:

(00:00) Incorporating AI into PreSales workflows
(01:49) Will AI replace PreSales roles?
(03:03) Boosting morale through AI-driven innovation
(04:20) AI-powered tools used by Docusign

In this episode, Jarod Greene sits down with David Yockelson, Distinguished Vice President and Gartner Fellow, as he shares his insights on how driving efficiency in collaborative efforts with account executives can lead to more effective business cases and stronger customer relationships.

In this episode, you’ll learn:

1. The Importance of Time in PreSales: David highlights how presales teams often struggle with managing their time effectively. Streamlining processes like demo automation and interactive demos can give them valuable hours to focus on higher-level tasks.
2. Collaborative Business Case Development: Learn how presales professionals can work more closely with account executives to build compelling, personalized business cases that resonate with customers and help drive sales.
3. Understanding Customer Needs: Discover how sales engineering teams can better understand and address individual customer needs, ensuring that solutions are relevant, impactful, and aligned with the customer’s unique goals.

Things to listen for:

(00:00) The most valuable commodity for pre-sales teams

(00:56) The challenges with time management

(02:13) How to effectively move prospects through the funnel

(03:13) The role of pre-sales in developing business cases

(04:23) The impact of demo automation on pre-sales efficiency

(05:51) Why ROI stories need to be personalized to the customer

In this episode of V5, host Jarod Greene chats with Tom Josephson, Director of Solution Consulting at TCP Software, about a controversial take: demos aren’t as crucial as everyone believes. Find out how mastering discovery can lead to deeper customer connections and more successful deals.

In this episode, you’ll learn:

• The Power of Discovery: Tom explains why understanding your buyer’s needs through effective discovery can give you an edge over competitors, even when pricing becomes a factor.
• Shifting the Focus: Setting clear expectations for demos ensures they are laser-focused on what matters most to the customer.
• Value-Based Selling: Tom shares insights on how to sell capabilities during discovery, getting buyers excited and showing alignment long before the demo.

Things to listen for:

(00:00) Demos don’t matter, discovery does

(00:45) Lessons Tom learned from the deals he lost and won

(02:07) Why strong discovery sets up the demo for success

(03:02) What to do when a prospective client requests early demos

(03:53) Steps to secure buy-in on the importance of discovery

In this episode, Jarod Greene, host of V5, and Deirdre Sommerkamp, Chief Solutions Officer at Skillibrium, discuss the benefits of assigning SEs based on their specific skills for different stages of the sales cycle. 

In this episode, you’ll learn:

1. The Power of Strengths-Based Sales Engineering: Deirdre introduces the concept of assigning multiple SEs to opportunities based on their unique strengths, leading to a more effective sales process.
2. The Importance of Collaboration and Continuity: Detailed note-taking and pre-call strategies are essential for maintaining seamless transitions and ensuring that every team member is aligned, regardless of who takes the lead in different stages of the sales cycle.
3. Adapting to Customer Preferences: Tailoring your sales engineering approach to fit the specific needs of your buyers is crucial, and flexibility in SE assignments can significantly impact customer satisfaction and sales success.

Things to listen for:
(00:00) Strengths-based approach to sales engineering

(01:51) How to balance continuity and specialization

(02:39) Importance of collaboration and note-taking

(03:43) “We-first” vs. “Me-first” mentality

(04:40) When using a strengths-based approach

In this episode, Matt Darrow, CEO and Co-founder of Vivun, and Joseph Miller, Co-founder and Chief Data Scientist at Vivun,  share how AI will affect sales engineering teams. They explore concepts like the integration of top-down and bottom-up approaches and how AI technologies are fundamentally altering the nature of labor in B2B sales. You’ll also learn the critical skills sales engineers need to have to stay competitive in an increasingly AI-driven market.

In this episode, you’ll learn:

1. The Evolution of AI: Joe takes us back to the fundamentals, explaining the top-down and bottom-up strategies that have helped AI evolve over the decades.
2. The Impact on Labor and Productivity: GenAI disruption is different from previous technological advancements, meaning they can’t be mitigated by retraining alone.
3. The Future of Sales Engineering: Sales Engineers will have to adapt to new AI tools, leveraging them for automation and strategic advantage.

Things to listen for:

(00:00) The evolution of AI

(01:14) Merging top-down and bottom-up approaches  

(04:22) We underestimate the advancements in AI technology  

(06:51) AI's impact on the future of work and labor disruption  

(13:55) How partial automation is shaping the future workforce   

(18:42) Usability challenges in the early stages of AI integration  

(20:08) Revolutionizing sales engineering with AI in solution design  

(22:27) Essential skills for sales engineers to adapt to AI

(25:48) Automating tactical work with AI to free up time for innovation

On The Unexpected Lever, we’re diving deep into what happens before the deal closes and why it’s more than just demo automation. It’s about understanding real problems and providing meaningful solutions. Brought to you by Vivun, this show celebrates the unsung heroes—sales engineers—who drive revenue growth by connecting with clients, solving challenges, and delivering results.

Whether you're aiming for stronger revenue, higher retention, or shorter sales cycles, remember: the pre-work makes the dream work. 

Tune in to learn how these strategies can transform your sales approach.