Grow & Tell

Fiona Simpson, Senior Revenue Enablement Business Partner at Boomi and Founder of ReflectPath, built her career enabling the exact functions she used to work in—CS, presales, and solutions consulting. Fiona shares how she's now building CS enablement at a $500M company, why most revenue teams only study failure (and what to do instead), the actual best use cases for AI in CS, and how to say no to stakeholders like a pro.

Stacey Justice, VP of GTM Enablement at Gong, breaks down Gong's detect-prescribe-validate enablement flywheel, how AI role play is replacing traditional certifications, and why "enablement" is her least favorite word in the dictionary.

Alex Kracov, Co-founder & CEO of Dock, and Eric Doty, Head of Marketing, break down why sales reps ignore most of the content enablement teams create—and what modern content management actually needs to look like in an AI-driven world.

Jonas Master, VP of Sales Enablement at Rippling, has scaled his team from 5 to 36 people while the sales org grew from 350 to 2,200+ reps across 35 product SKUs—and argues that most enablement teams optimize for the wrong things. 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.

Alex Kracov, founder and CEO of Dock, and Eric Doty, Head of Marketing, dig into the current and near-future state of AI in sales enablement—breaking down what's actually working, why data infrastructure matters more than buying new tools, and how to think about AI-powered selling as the space evolves.

Sheevaun Thatcher, VP Revenue Enablement at Demandbase—who previously built a 162-person enablement team at RingCentral during a $300M to $2B revenue run—shares her "Responsible To, Not For" philosophy that transformed how enablement partners with sales leadership, her Five Questions framework for ruthless prioritization, and why the biggest enablement failure isn't bad training but managers who don't know how to coach.

Justin Driesse, Director of Sales Enablement at Legora, drove $105M+ in pipeline as the architect of Slack AI's global enablement strategy before building AI-native programs at Writer and now the $1.8B legal AI startup. 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.

Ryan Vanshur, VP of GTM Intelligence & AI Solutions at Handle, spent 10 years co-founding CourseKey—growing it to 200+ career college customers, 99% retention, and a private equity exit—and now brings that founder-operator DNA to construction FinTech, where he's built one of the most AI-forward enablement programs in B2B SaaS—covering 90-day vertical immersion curricula, AI-powered deal coaching, and why the future belongs to internal micro-SaaS over off-the-shelf tools.

Alex Kracov, founder and CEO of Dock, and Eric Doty, Head of Marketing, walk through the full anatomy of a product launch at Dock—from roadmap planning and messaging development to sales training, soft launches, and marketing tactics.

Morgan Kassel, Senior GTM Enablement Manager at Vanta, has been part of building enablement from the ground up at a $4B+ unicorn. 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.

Alex Kracov, founder and CEO of Dock, and Eric Doty, Head of Marketing, break down what early-stage sales enablement actually looks like before you have a dedicated hire—covering who should own it, when to keep things loose versus documented, and the signals that tell you it's time to bring someone on.

Trafford Judd, VP of Operations at Intenseye, built enablement teams at LinkedIn, Slack (during the $28B Salesforce acquisition), and Asana (leading 18 people supporting a $700M+ revenue org). He shares how his HR background shapes his approach to enablement, why manager enablement is the key unlock most companies miss, and how AI is making it harder than ever to be a buyer in B2B sales.

We're finally back with a new season of Grow & Tell after taking most of 2025 off to focus on building Dock. 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 LatticeWhy we initially tried to build for every B2B relationship (data rooms, agencies, recruiting) before narrowing to sales and onboardingHow focusing on enablement leaders as the ICP simplified everything—sales, product, customer successWhy we shifted from a product-led growth motion to a hybrid sales-led approachWhat makes legacy enablement platforms vulnerable, and how AI has leveled the playing field for startupsThe content flywheel strategy behind relaunching the podcastEnjoy the show!

Don Otvos, RevOps leader and current GTM Strategist and Platform Evangelist at Chili Piper, shares the story of how one difficult conversation with a former boss made him switch career tracks after 20 years in sales.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 shifthis memorable job interview with David Sackshow an appearance in First Round Review landed him a job at SalesLoftbehind the scenes of the partner programs at LeanData and Chili Piper

Melissa Rosenthal's first job out of college was as an intern at BuzzFeed. In her 6 years with the company, she rose to Global VP of Creative, delivering more than $50M in native ad revenue and $100M in branded content.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 BuzzFeedWhy ClickUp was willing to take a shot on brand-forward marketingWhat she's building at her new company, Outlever

Catie Ivey is the Chief Revenue Officer at Walnut — a leader in interactive demo platforms.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 MarketoSelling an ABM product at DemandbaseShifting to a new customer persona at PendoLife 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.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 hireThe best way for CS to handle product feedbackWhy live training sessions aren’t always the best way to onboard clientsHow to be more proactive about winning renewals

Most of our guests are builders, but Wynne Brown is a fixer. Learn how she's slashed churn, expanded renewals, and professionalized Sales and CS teams at Monster, GitHub, Seal Software/Docusign, Fable, RocketReach, and more.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 divisionLeading CS at GitHub, where she introduced enterprise CSMsTurning around a huge churn problem at Seal SoftwareLeading revenue at Fable and RocketReach through their Series A

Chris Michelmore, Head of Mid Market Acquisition at Zoom, tells the nine-year story of how he ascended from first-time SDR to senior sales leader.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 sellerWhy coaching sales reps is more like selling than you'd thinkThe big differences between leading sales directors vs. AEsWhat it’s like growing alongside a company in hypergrowth

Matt Green, Co-Founder and CRO of Sales Assembly, shares the company's founding story, the keys to a great sales training program, plus the biggest sales skills most teams are missing today.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 trainingwhat today's most successful sales leaders are talking aboutthe 2 biggest skills that sales teams are missingthe most common struggles he sees with new sales leadershis advice for selling through champions

Monica Perez, Head of Customer Success at Notion, shares the four-year journey of building Notion's foundational CS team.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 structuredthe relationship between sales and CShow they mature customer accounts over timehow they measure the success of their CS programs

Devin Bramhall, growth advisor and former CEO of Animalz—the content marketing agency for companies like Amazon, Google, and Intercom—shares candid stories about 3xing the agency's revenue to $11.5M in only 2 years.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 AnimalzHer advice for startups thinking about contentHow she grew her podcast

Eloise (Shuttleworth) Salisbury, newly named Chief Customer Officer at AutogenAI, recounts lessons from 5 years of building Iterable's customer success program from the ground up, how she's approaching her first 90 days in a new CS leadership role, and why she founded Women in SaaS.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 teamswhat makes an ideal CS/sales relationshiphow she's approaching the first 90 days at AutogenAIwhy she founded Women in Saas (and her advice for women in tech leadership)

Derek Osgood, Founder & CEO of Ignition, shares product marketing lessons from leading 9 major launches at PlayStation, reinventing a software category at Rippling, and founding Ignition—a product management platform.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 SaaShow Rippling thought about reinventing a product categorytransitioning to the role of founder at his own companyhis best practices for a successful product launch

Jen Igartua, CEO at Go Nimbly, shares what she's learned in her 8 years of building a service-based business, plus tons of advice for RevOps teams.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, CMO of ShipBob, shares marketing lessons from his 5 years growing ShipBob to a $1b valuation. 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 channelsCasey's advice for partnering with bigger brandsHow they built out their marketing teamHow their messaging has evolved with their ICP

Open AI's Conor Dragomanovich shares his personal sales career growth story at Productboard, where he went from founding AE to VP of Commercial Sales in only 5 years.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 aboutProductboard's early product-led sales processWhat it was like to transition into an enterprise roleThe transition from managing reps to managing managersHow to hire a founding AEWhat sales looks like at OpenAI

Chris Gadek, CRO at AdQuick, shares the company's growth story and best practices for out-of-home advertising in B2B.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 marketplaceHow AdQuick digitized an old-school industryWhat you need to run a strong billboard campaign

Lish Barber, Senior Director of Enablement at Sigma Computing, shares stories and lessons from building early enablement programs at iHeartMedia, Algolia, and Sigma Computing.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 kickoffWhere sales enablement sits on a cross-functional teamWhat tools should be in every enablement tech stack

Pete Hancock, former VP of National Sales at Yelp and current SVP of Global Sales at Restream, shares stories from the early days of Yelp's go-to-market plan.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 YelpYelp’s intense sales training programHow they built a community marketplace around the productPete’s transition to selling national accountsThe impact Yelp’s sales culture has had on the broader industry

Kyle Norton, CRO of Owner, shares learnings from launching Shopify's retail POS program and building Owner's sales team.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 LeagueWhy he made the move from startups to ShopifyShopify's POV sales pitchWorking with a first-time founder at Owner

Hector Hernandez, CRO at Teleport, shares sales lessons from taking two developer-focused platforms — LaunchDarkly and Teleport — upmarket.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 modeHow to move upmarket in the developer tech spaceHow selling to developers changed in 2023How to enable a great remote sales culture

Jason Fishkind recounts Sprinklr's sales journey from $5m to $500M in ARR.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 daysCharacteristics of a successful sellerHow he kept up with Sprinklr’s growthTips for selling enterprise AI tools

Robby Allen, CRO of AgentSync, shares sales leadership stories from his time as Director of Sales Development at Zenefits.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 leaderSpinning up Zenefits' outbound strategyWhy AgentSync hired scrappy AEs before enterprise repsThe difference between being a CRO and VP of SalesWorking with Jason Lemkin at SaaStr

Chris Orlob shares his unlikely origin story as Gong's first marketer, sales leadership advice, and what it was like to transition entrepreneurship at Pclub.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 GongThe explosive growth of Gong LabsTransitioning from marketing to sales leadershipCo-Founding Pclub.io and QuotaSignal

Todd Busler shares how his path from first go-to-market hire to VP of Sales at Heap led him to found his own tech company, Champify.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 growthThe evolution of Heap's competitive messagingHow the sales landscape has changed over timeThe differences between being an early sales hire vs. a founder

Nico Dato, CMO of Entrata, shares lessons from growing Podium from a single-product review platform to a nine-figure, multi-product lead gen platform.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 tradeshowsThe two most important relationships for every marketing leader (spoiler: it's Product and Sales)Why MQLs are a deceptive metricPlanning Entrata's massive user conferenceWhy you shouldn’t sleep on Utah as a tech hub

Marie Gassée, Head of Go-to-market at Column, shares stories of growing self-serve at Box and Confluent.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 programSelling to open-source users at ConfluentEarly growth lessons from ColumnScaling herself along her career journey

Joseph Schmitt, VP of Success at UpKeep, shares his learn-by-doing approach to growing Customer Success teams. 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 leadershipJoining UpKeep as their first CS hireHiring and retaining UpKeep’s CS team for the past 6 yearsStructuring UpKeep’s CS teamsWorking with a non-tech-savvy customer baseAdvice for early CS hires

Peep Laja, co-founder of Wynter, CXL, and Speero, shares lessons from bootstrapping multi-million-dollar businesses from scratch. Plus, he shares messaging lessons from Wynter.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 companiesAdvice for company positioning and messagingWhy he moves upmarket as fast as possibleWynter’s growth and marketing strategy

Peter Kazanjy, author of Founding Sales and co-founder of Atrium, shares sales advice for startup founders and early sales hires.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 TalentBinWriting Founding SalesEvolving past founder-led salesDemocratizing sales metrics at AtriumThe datafication of salesBuilding the Modern Sales Pros community

Camille Ricketts, former Head of Marketing at Notion, shares how Notion through 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 & B2CBuilding and scaling an engaged communityPartnering with ambassadors and influencersInfusing ubiquity and emotion into Notion’s marketing strategyAdvice for community-led growth

Gillian Heltai, Chief Customer Officer at Lattice, shares her experience in building customer experience programs at Lattice, Talkdesk, and comScore.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 comScoreGoing on a customer listening tour at Talkdesk to create a new onboarding program for upmarket customersJoining Lattice after its Series CHow Lattice structures its CX teamsAdvice for onboarding, health scoring, renewals, and more

Marketing leader Maya Spivak shares what went into launching successful brand campaigns at Wealthfront and Segment.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 challengesTech-driven investing trust and the role of launch videosThe strategy behind Wealthfront’s 35 commercialsMaya’s B2B marketing journey with SegmentEvolving brands, user conferences, and billboard advertising insights

Ben Solari, VP of Sales at Jellyfish, shares sales advice for taking technical products to market.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 backgroundHow Ben learned to sell technical productsDataRobot and Jellyfish's early sales strategiesScaling DataRobot's sales team to 30 account executivesJellyfish's top-down sales pitchCollaborating with marketing

Alexa Grabell, Founder of Pocus, shares the company's founding story, plus lots of product-led growth advice for go-to-market teams.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 foundingPocus's approach to fundraisingThe role of sales in a product-led motionWhen PLG companies should hire their first sales repWhy Pocus isn't a product-led company themselvesAnd a bunch of other PLG best practicesEven 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.

Bryan Rutcofsky, Co-Founder and CRO of Marqii, shares how he grew sales at Yext to over 140 team members and $100 million in revenue.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 YextThe challenges of selling a new product category to several SMB verticalsWhy he hired primarily junior sales reps for their first 100 hiresHow he came to co-found his new company, MarqiiWhat it's like selling into the hospitality industryEnjoy the conversation!

Rich Liu, CRO of Everlaw, recounts stories from his time leading early sales at Facebook in 2010, taking the plunge into B2B SaaS at MuleSoft, and selling a corporate travel platform during the pandemic.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” IPOHow he transformed MuleSoft's sales model from a technical sale to an outcome-based saleHow he hired a sales team at scale after MuleSoft was acquired by SalesforceSelling to economic buyers through the pandemic at TripActionsSelling in a down market at Everlaw

Ben Braverman, Chief Business Officer of Hadrian and former CRO of Flexport, shares how he grew Flexport to an $8 billion valuation.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 customersWhy Flexport started with the long tail of SMB customersWhy Ben scaled the sales team slowlyWhat makes a great SMB vs. mid-market vs. key accounts sales repFlexport’s selling squadsHow they ramped up new sellersThe double-edged sword of succeeding as a first-time revenue leaderHis 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.

Tushar Makhija, Founder and CEO of TeamOhana, chats with Alex about how he went from zero sales experience to VP of revenue at HelpShift in only a few years, what it means to be a sales leader, and why Indian immigrants are so successful in tech leadership positions.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 HelpshiftWhat it was like to go from startup mode to working with a professional CEO at HelpshiftAdvice for first sales hiresWhat it means to be a sales leaderThe difference between being a sales leader and a founderWhy Indian immigrants are so successful in tech leadership positions.