He breaks down Rippling's highly specialized enablement model with 65 distinct onboarding tracks, the time-and-motion study that revealed where sellers waste hours daily, and why training sentiment scores are the least valuable metric you can measure.

He shares why enablement needs to get out of the content business, how two Notion-based AI agents generated 300 account plans in nine business days for his sales team, and what "seller empathy" actually looks like in practice.

She shares how the program scaled from two people to 13, the "Sports Center Top 10" coaching framework, a competitive intelligence program called the CIA, and why manager reinforcement is the most underrated lever in enablement.

We're re-launching with a new format: half interviews with enablement and go-to-market leaders, half conversations between Alex Kracov, CEO of Dock, and Eric Doty, Head of Marketing, about what it's really like to build a B2B SaaS company from the ground up.

In this first episode back, we walk through Dock's entire journey so far—from Alex's initial experiments with a Webflow microsite at Lattice to today's bet on becoming an AI revenue enablement platform. It's a candid look at the pivots, mistakes, and market signals that shaped the company.

We discussed:

• How Alex got the idea for Dock after noticing sales reps couldn't share content effectively at Lattice
• Why we initially tried to build for every B2B relationship (data rooms, agencies, recruiting) before narrowing to sales and onboarding
• How focusing on enablement leaders as the ICP simplified everything—sales, product, customer success
• Why we shifted from a product-led growth motion to a hybrid sales-led approach
• What makes legacy enablement platforms vulnerable, and how AI has leveled the playing field for startups
• The content flywheel strategy behind relaunching the podcast

Enjoy the show!

Since then, he has networked his way to a successful RevOps leadership career at companies like Yammer, SalesLoft, and LeanData.

Don Otvos has built an entire career in RevOps off the back of thoughtful networking and product evangelism.

After an honest conversation with a manager led him to a career in revenue operations, he’s held sales & RevOps leadership roles at companies like Yammer, SalesLoft, and LeanData.

This week, Don joins Alex to share his greatest hits, including:

• how he networked himself into a major career shift
• his memorable job interview with David Sacks
• how an appearance in First Round Review landed him a job at SalesLoft
• behind the scenes of the partner programs at LeanData and Chili Piper

She also helped ClickUp 100X their revenue growth as their Chief Creative Officer. Today, she's the co-founder of Outlever, a new startup that helps companies become the #1 news source in their industry.

For our 40th episode, we’re talking to Melissa Rosenthal.

As BuzzFeed’s Global VP of Creative, she led a team that created over 3,000 branded content campaigns, earning hundreds of billions of views, over $100M in revenue for BuzzFeed, and a spot on Forbes’ 30 Under 30.

As ClickUp's CCO, Melissa grew their ARR from $2 to $200M in 4 years and ran some memorable billboard campaigns. 

On today’s episode, Melissa breaks down the most memorable stories from her career, including:

• How she scaled herself at BuzzFeed
• Why ClickUp was willing to take a shot on brand-forward marketing
• What she's building at her new company, Outlever

Catie has built a standout career in sales, leading teams at some of the biggest names in marketing tech, including Marketo, Demandbase, and Pendo.

Today, we’re taking a journey through pivotal moments in Catie’s career that shaped her approach to sales leadership.

Catie Ivey has built a dream career in sales, leading teams at some of the biggest names in marketing tech.

Today, she's joining Alex to break down her advice for aspiring sales leaders, and her biggest tips for interactive demos that convert.

Catie also takes us through pivotal moments in her career, including:

• The private equity acquisition at Marketo
• Selling an ABM product at Demandbase
• Shifting to a new customer persona at Pendo
• Life as a startup CRO at Walnut

Nobody prepares you for the jump from CSM to CS leader. But Rachel Provan is trying to change that.

Rachel is a customer success leadership coach, helping CS leaders and early-stage companies build customer success strategies and leadership habits that scale.

She joined Alex to discuss the psychology and strategy behind CS, including:

• When a founder should make their first CS hire
• The best way for CS to handle product feedback
• Why live training sessions aren’t always the best way to onboard clients
• How to be more proactive about winning renewals

Wynne Brown spent the last two decades coming into scaling companies with leaky revenue — where she rights the ship, and then moves on to the next challenge.

She’s revamped Sales and Customer Success at companies like Monster, GitHub, Fable, and RocketReach - mostly by focusing on the customer.

This week, Wynne joins Alex to discuss her career journey, including:

• Introducing Customer Success to Monster’s military.com division
• Leading CS at GitHub, where she introduced enterprise CSMs
• Turning around a huge churn problem at Seal Software
• Leading revenue at Fable and RocketReach through their Series A

It's rare for a first-time SDR to stick around long enough to become a sales leader at that same company.

But that's exactly how Chris Michelmore became the Head of Mid Market Acquisition at Zoom.

This week, he's taking Alex through his journey up the company ladder, including:

• What made him so successful as a seller
• Why coaching sales reps is more like selling than you'd think
• The big differences between leading sales directors vs. AEs
• What it’s like growing alongside a company in hypergrowth

Some of today's best companies started over a cup of coffee.

That's how Matt Green and his co-founder, Jeff Rosset, started Sales Assembly – the go-to sales resource for some of the world's best B2B tech companies.

Matt joins Alex this week to share the growth story of Sales Assembly, including:

• why they pivoted from role-backed to skill-based training
• what today's most successful sales leaders are talking about
• the 2 biggest skills that sales teams are missing
• the most common struggles he sees with new sales leaders
• his advice for selling through champions

Customer Success at a product-led company is a completely different animal.

When Monica Perez was brought in to grow Notion's foundational customer success team, they were already at $40 million in revenue.

Today, Monica joins Alex to discuss what it was like to build a CS program on top of a strong PLG engine — including:

• how their customer onboarding is structured
• the relationship between sales and CS
• how they mature customer accounts over time
• how they measure the success of their CS programs

Devin Bramhall is a content marketing legend.

After 3xing revenue to $11.5M in only 2 years at Animalz, she went on to build a successful consulting biz while growing her marketing podcast, Don't Say Content.

This week, Devin joins Alex to discuss:

• How she scaled Animalz
• Her advice for startups thinking about content
• How she grew her podcast

What does it take to build an enterprise-level customer success program?

Eloise Salisbury, Chief Customer Officer at AutogenAI, joins us this week to break down what she learned scaling Iterable's customer success program.

Eloise joined Iterable, a cross-channel marketing enablement platform, after their Series B. 

In her five years with the company, she scaled their CS to an international audience, introduced an enterprise CS and implementation track, which ultimately helped the company grow to a $2 billion valuation.

In today’s episode, Alex and Eloise discuss:

• how to build mid-market and enterprise CS teams
• what makes an ideal CS/sales relationship
• how she's approaching the first 90 days at AutogenAI
• why she founded Women in Saas (and her advice for women in tech leadership)

Derek Osgood is a career product marketer turned founder.

He's made a career out of leading product launches at PlayStation and Rippling before founding Ignition, a go-to-market platform designed to help businesses launch products.

In today’s show, Derek joins Alex to talk about:

• how his PlayStation game launch experience lends itself to SaaS
• how Rippling thought about reinventing a product category
• transitioning to the role of founder at his own company
• his best practices for a successful product launch

Jen Igartua, CEO of Go Nimbly, joins Alex on this week's episode to talk all things RevOps.

First she uncovers what went into building her RevOps consultancy, including how they developed their service offerings, how they stay profitable, and how they recruit talent.

Then, Jen and Alex dive deep into RevOps, where Jen shares tips on building a RevOps roadmap, structuring a RevOps team, and picking your tool stack.

Casey Armstrong knows his way around ecommerce marketing – he's led both B2B and B2C marketing teams during his career.

On this week's episode, Alex and Casey go deep on ShipBob’s startup marketing strategy, including:

• Why they started with only a few channels
• Casey's advice for partnering with bigger brands
• How they built out their marketing team
• How their messaging has evolved with their ICP

As a two-time founding AE, Conor Dragomanovich knows all about what it takes to start and build a successful sales team.

On today's episode, Conor and Alex chat about

• Productboard's early product-led sales process
• What it was like to transition into an enterprise role
• The transition from managing reps to managing managers
• How to hire a founding AE
• What sales looks like at OpenAI

Out-of-home advertising is one of the most underrated strategies for B2B startups.

Billboards might feel like a tactic reserved for large corporations, but Chris Gadek from AdQuick actually recommends them for Series A startups.

That's why he's joining us for a crash course on running out-of-home ads.

On this week's episode, Alex and Chris discuss:

• Building AdQuick's two-sided marketplace
• How AdQuick digitized an old-school industry
• What you need to run a strong billboard campaign

After starting her career in sales at iHeartMedia, Lish Barber accidentally fell into a sales operations role overnight. 

It was there that she started her long career in enablement — building programs for technical products like Algolia and Lattice before landing her current role at Sigma Computing.

In today's episode, Lish and Alex talk all things enablement, including:

• How to balance product vs. process in technical sales education 
• What goes into a great sales kickoff
• Where sales enablement sits on a cross-functional team
• What tools should be in every enablement tech stack

During his 11 years at Yelp, Pete Hancock helped the then-startup grow from $1m in revenue to over $750m.

He also built a rigorous sales program that trained thousands of AEs.

In this episode, Alex and Pete discuss:

• What sales looked like in the earliest days of Yelp
• Yelp’s intense sales training program
• How they built a community marketplace around the product
• Pete’s transition to selling national accounts
• The impact Yelp’s sales culture has had on the broader industry

Kyle Norton has led sales teams at two unicorn companies — League and Shopify.

While leading sales at League, he grew revenue to $20 million and scaled their sales team to 40 reps.

3 years later, he joined Shopify as Head of Revenue for their retail division to help roll out their point-of-sale products.

In today's episode, Kyle joins Alex to discuss:

• Building 3 sales motions from scratch at League
• Why he made the move from startups to Shopify
• Shopify's POV sales pitch
• Working with a first-time founder at Owner

When Hector Hernandez joined LaunchDarkly in 2017, they already had $1 million in revenue. Instead of focusing just on scaling, they were looking for a sales team to help them evolve past their PLG motion.

Since then, Hector has helped LaunchDarkly grow to over $60M in revenue and a $3B valuation.

3 years later, he repeated his success with Traceable AI—helping them reach a $60M series B.

On today's episode, Alex and Hector go behind the scenes to uncover:

• What it’s like to join a company in scale mode
• How to move upmarket in the developer tech space
• How selling to developers changed in 2023
• How to enable a great remote sales culture

Sprinklr is one of the biggest names in social media management, but it didn't start out that way.

As Sprinklr's first AE, Jason Fishkind helped the company 100x their growth from $5M to $500M ARR -- accelerating them through their IPO and earning a valuation of over $4 billion.

On today's episode, Jason joins us to talk about a decade of sales growth at Sprinklr, including:

• What it was like to sell social media in the early days
• Characteristics of a successful seller
• How he kept up with Sprinklr’s growth
• Tips for selling enterprise AI tools

Zenefits is one of the most infamous hypergrowth stories in SaaS history, growing to over $70 million ARR and a $4 billion valuation from 2013 to 2016.

But their hypergrowth came at a cost. Insurance compliance issues resulted in millions of dollars of fines, a leadership shakeup, and mass layoffs in 2017.

Robby Allen was there for all of it — bringing some key lessons from Zenefits to his next venture, leading sales at AgentSync.

On today's episode, Alex and Robby discuss:

• Transitioning from SDR to sales leader
• Spinning up Zenefits' outbound strategy
• Why AgentSync hired scrappy AEs before enterprise reps
• The difference between being a CRO and VP of Sales
• Working with Jason Lemkin at SaaStr

In 2015, Chris faced tough competition when his newly founded company, Conversature, went up against Gong -- the eventual category winner.

Although he was forced to close his doors just one year later, a new one opened at Gong.

After joining as Gong's Head of Product Marketing, Chris started Gong Labs, one of the most successful content marketing programs in SaaS, and helped grow Gong from $200k to $200M ARR and a $7.2B valuation.

In 2022, he left Gong and leveraged his audience into co-founding Pclub.io — a sales learning platform, and QuotaSignal — a tech-enabled revenue team hiring service.

On today's episode, Alex and Chris discuss:

• Going from competitor to Product Marketing Director at Gong
• The explosive growth of Gong Labs
• Transitioning from marketing to sales leadership
• Co-Founding Pclub.io and QuotaSignal

Being an early sales hire is a great test run for being a founder.

As the first sales hire at Heap, Todd helped the company grow from $300k to $40 million ARR and 10x their average contract value.

Six years later, he co-founded Champify, helping GTM teams sell more effectively with one innovative tool.

In today’s episode, Alex and Todd discuss:

• How internal sales competition led to Heap’s growth
• The evolution of Heap's competitive messaging
• How the sales landscape has changed over time
• The differences between being an early sales hire vs. a founder

When Nico Dato joined Podium in 2015, they were a single-product review tool for SMBs with under $1m in revenue.

Over a 7-year period, Nico helped grow Podium to a multi-product lead conversion platform with over $100m in revenue. 

For those counting at home, that's 100x growth.

In today’s episode, Alex and Nico discuss:

• How Podium grew primarily through webinars and industry tradeshows
• The two most important relationships for every marketing leader (spoiler: it's Product and Sales)
• Why MQLs are a deceptive metric
• Planning Entrata's massive user conference
• Why you shouldn’t sleep on Utah as a tech hub

Marie Gassée has an impressive track record building growth programs.

She led the launch of Box’s product-led motion and helped Confluent commercialize its open-source developer community.

But none of that growth came easy.

On today's episode, join Alex & Marie as they discuss:

• Building Box’s self-serve program
• Selling to open-source users at Confluent
• Early growth lessons from Column
• Scaling herself along her career journey

Joseph Schmitt is exactly the type of growth story we like to tell—from a few perspectives.

He’s had a surprisingly fast personal career arc from entry-level support to senior Customer Success leader and also helped grow two startup customer success teams from the ground up.

On today’s show, Joseph and Alex chat about:

• Transitioning from entry-level support to management & senior leadership
• Joining UpKeep as their first CS hire
• Hiring and retaining UpKeep’s CS team for the past 6 years
• Structuring UpKeep’s CS teams
• Working with a non-tech-savvy customer base
• Advice for early CS hires

Peep Laja is an expert at bootstrapping companies.

He started by turning his in-house marketing experience into a consultancy…

He took that consultancy and scaled it into an agency…

He used the profits from his agency to bootstrap an e-learning business…

And then he took the profits from his elearning business to bootstrap a SaaS company.

In today’s episode, Peep and I discuss:

• The founding stories behind his three companies
• Advice for company positioning and messaging
• Why he moves upmarket as fast as possible
• Wynter’s growth and marketing strategy

Pete Kazanjy literally wrote the book on founder sales.

As a three-time startup founder, Pete knows the ins and outs of building an early-stage sales team.

On today's episode, Alex and Pete discuss:

• Pivoting his first startup to TalentBin
• Writing Founding Sales
• Evolving past founder-led sales
• Democratizing sales metrics at Atrium
• The datafication of sales
• Building the Modern Sales Pros community

You don’t go from unknown startup to household name without a great community strategy. That was definitely the driving factor behind Notion's growth.

As the 11th hire and Head of Marketing at Notion, Camille Ricketts built the brand foundations that enabled Notion to take off like a rocket ship.

On this week's episode, Alex and Camille discuss:

• Positioning Notion as a broad product for B2B & B2C
• Building and scaling an engaged community
• Partnering with ambassadors and influencers
• Infusing ubiquity and emotion into Notion’s marketing strategy
• Advice for community-led growth

As Gillian puts it, she worked in customer success long before anyone called it customer success.

Since then, she's helped build successful CX programs at comScore, Talkdesk, and now Lattice.

On today's episode, Alex and Gillian discuss:

• Growing from entry-level analyst to Senior VP at comScore
• Going on a customer listening tour at Talkdesk to create a new onboarding program for upmarket customers
• Joining Lattice after its Series C
• How Lattice structures its CX teams
• Advice for onboarding, health scoring, renewals, and more

What goes into creating a tech brand that not only stands out but deeply resonates with its audience?

Maya Spivak, an experienced brand and marketing expert, joins us in this episode to share her experience building TV and billboard campaigns for Wealthfront and Segment.

In today's episode, Alex and Maya discuss:

• Wealthfront's transformation and branding challenges
• Tech-driven investing trust and the role of launch videos
• The strategy behind Wealthfront’s 35 commercials
• Maya’s B2B marketing journey with Segment
• Evolving brands, user conferences, and billboard advertising insights

If you’re not super technical, sales is a great way to get your foot in the door in the startup world. That’s how Alex (our host) got started at Yelp before eventually founding Dock.

But what happens when you have to sell a very technical product to a very technical audience?

Ben Solari joins us in this episode to talk about leading sales teams at DataRobot and Jellyfish—two products aimed at engineering leaders.

Alex and Ben discuss:

• The benefits of being a seller with an equities trading background
• How Ben learned to sell technical products
• DataRobot and Jellyfish's early sales strategies
• Scaling DataRobot's sales team to 30 account executives
• Jellyfish's top-down sales pitch
• Collaborating with marketing

Pocus has ridden the PLG wave, earning $23 million in funding and landing big-name SaaS customers like Webflow, Loom, and Miro only two years since its founding.

In today’s episode, Alex and Alexa discuss:

• The backstory behind Pocus's founding
• Pocus's approach to fundraising
• The role of sales in a product-led motion
• When PLG companies should hire their first sales rep
• Why Pocus isn't a product-led company themselves
• And a bunch of other PLG best practices

Even if you’re not in PLG, there’s tons of gold sales and go-to-market advice in this episode. 

It was only 3 years ago that Alexa Grabell was working in a sales operations role at Dataminr. 

She realized how much-untapped value was sitting in product and customer data.

After going back to school to complete an MBA at Stanford in 2021, Alexa co-founded Pocus—a revenue data platform that helps go-to-market teams surface insights from their product usage data.

Through building Pocus, Alexa has become one of the leading voices in product-led growth (PLG) and product-led sales.

Inflated job titles are a bit of a cliche at startups. You see a lot of C-suite and VP-level roles that probably shouldn’t have been handed out.

But when Bryan Rutcofsky grew sales at Yext to 140 team members and over $100 million in revenue, he certainly earned the Senior VP title.

When Bryan joined Yext, they were called GymTicket.com — a local listings website that sold leads to gyms. They later expanded into other categories, like veterinarians and TV repairmen, before wrapping everything into one website: Yext.

By the time Bryan left Yext in 2017, they were listed on the New York Stock Exchange.

In today’s episode, Bryan shares:

• What it was like to lead sales as they built and re-built Yext
• The challenges of selling a new product category to several SMB verticals
• Why he hired primarily junior sales reps for their first 100 hires
• How he came to co-found his new company, Marqii
• What it's like selling into the hospitality industry

Enjoy the conversation!

Rich Liu’s philosophy to scaling sales at 5 unicorn companies has been surprisingly simple: build the sales process to help the customer achieve their business outcomes.

In this episode, Alex and Rich talk about:

• The early days of sales at Facebook, including selling ads through the 2012 presidential election, the threat of mobile, and Facebook’s “black eye” IPO
• How he transformed MuleSoft's sales model from a technical sale to an outcome-based sale
• How he hired a sales team at scale after MuleSoft was acquired by Salesforce
• Selling to economic buyers through the pandemic at TripActions
• Selling in a down market at Everlaw

Flexport is a freight forwarder. They help book, track, and deliver freight shipments. So not only did Flexport’s sales team have to cope with the usual challenges of growing a SaaS company, they also had to handle the real-world logistical challenges that come from working with factories, customs agencies, and 747s. Alex and Ben became friends when Flexport invested in our company: Dock.

In this episode, Alex and Ben talk about:

• The importance of solving complete problems for your customers
• Why Flexport started with the long tail of SMB customers
• Why Ben scaled the sales team slowly
• What makes a great SMB vs. mid-market vs. key accounts sales rep
• Flexport’s selling squads
• How they ramped up new sellers
• The double-edged sword of succeeding as a first-time revenue leader
• His new role at Hadrian, the future of space manufacturing, and “space lasers”
• He’s also our first-ever guest to call in from a pickup truck in Wyoming.

Some revenue leaders thrive in the chaos of early startup life. They love getting their hands dirty, leading early sales deals, finding product-market-fit and establishing a go-to-market foundation.

Tushar Makhija is one of those people.

In this episode, Tushar and Alex chat about:

• How Tushar went from first-time sales rep to VP of revenue in only a few years at Helpshift
• What it was like to go from startup mode to working with a professional CEO at Helpshift
• Advice for first sales hires
• What it means to be a sales leader
• The difference between being a sales leader and a founder
• Why Indian immigrants are so successful in tech leadership positions.

Alex met Brittany while building Dock and was super impressed with her knowledge of building customer success and onboarding programs.

In her first year-plus at Loom, she has helped revamp their customer onboarding program, technical implementation process, customer-facing resource hub, live webinar program, Sales-to-CS handoff process, and much more.

In this episode, Brittany shares:

• what it’s like to work in Customer Success Enablement vs. Customer Success
• how to build a successful onboarding program; and
• how to measure onboarding success.

And stick around 'til the end to hear Brittany’s number one tip for sending better Looms.

The lines between sales-led and product-led growth are blurring. What used to be two distinct sales motions are now complementary to each other.

In this episode we talk to Pete Prowitt—who’s worked for some of the most successful companies in both sales-led and product-led growth.

We talk about:

• the differences and similarities between sales-led and product-led growth
• what it was like to be at Intercom and Loom during hypergrowth; and
• how he made the shift from successful sales rep to revenue leader

Enjoy the show!

François Dufour was Alex's coach back when Alex ran marketing at Lattice. François really helped Alex transition from being an individual contributor to a true marketing executive at a fast-growing SaaS company. 

In this episode, François and Alex caught up to talk about:

• early growth at LinkedIn and Twilio
• the importance of getting close to customers
• how to market and sell to a technical audience; and
• how to upgrade yourself from individual contributor to marketing leader

Enjoy the show!

Dini and Alex also happen to go way back. They worked together for 3 years at Lattice, where Dini ran sales and Alex ran marketing. So we thought she’d be the perfect guest for our new show.

In this episode, Alex and Dini about the early days at Lattice—including their go-to-market strategy, how they moved upmarket, and how they collaborated across sales and marketing.

Plus, Dini gives advice on how to grow from an AE to CRO. Enjoy the episode!

Nobody’s prepared to grow a billion-dollar business from square one. So, we're learning from revenue leaders who have already done it. Join host Alex Kracov, former VP of Marketing at Lattice and now Founder and CEO of Dock, as he has candid conversations with successful revenue leaders about their business growth stories.

From sales and marketing to customer success, we'll explore the growing pains and triumphs. Founders who have built companies from the ground-up will share their insights, while agencies and consulting firms behind the scenes of the fastest-growing companies in the world will reveal their secrets.

If you crave true, challenging stories of what it takes to grow revenue—no generic, high-level advice—then this show is for you.

Subscribe now on your favorite podcast platform and join us on the Grow and Tell Podcast. Let's dive deep into the world of revenue growth and learn from those who have walked the path of success.