The GTMnow Podcast
The GTMnow Podcast features interviews with well-known tech executives, VCs, and founders who share their experiences and insights on go-to-market strategies. Hosted by Sophie Buonassisi, each episode delves into the successes and failures of building fast-growing software companies. The podcast is produced by GTMnow, the media brand of GTMfund, an early-stage VC fund investing in B2B SaaS companies. Listeners gain practical advice from industry leaders at companies like DocuSign, Salesforce, and LinkedIn.
Episodes
Inside Merge: The $75M Bet on Open Source AI (Powering OpenAI, Netflix & Uber) | Shensi Ding, CEO
The Co-Founder & CEO of Merge joins GTMnow to break down how she built a company that now powers integrations for OpenAI, Perplexity, Netflix, Uber, Mistral, and enterprise logos like Mastercard, JP Morgan, and Amex, backed by $75M from Accel and NEA.Shensi gets tactical on the GTM decisions behind that growth: why she went enterprise-first into greenfield, why she's now layering a self-s
The Blueprint for a High-Performing Sales Team | Brian Le, Notion
Are your sales compensation plans driving the right behaviors or causing your best reps to quit? In this episode of GTMnow, Brian Le (Global Sales Compensation Partner at Notion) breaks down how to build a scalable sales comp operating system.Brian shares his firsthand experience scaling Notion's sales comp from 80 to over 400 employees and explains why trust is the ultimate currency in reven
VC: How a 2-Person Fund Runs Like a Startup (Memos, KPIs, R&D) | Vanessa Larco, Premise (ex-NEA)
"Investing in companies that OpenAI won't kill." That's Vanessa Larco's thesis, and in this VC bonus episode of GTMnow she breaks down exactly how she decides what survives. Vanessa, founder and GP at Premise (formerly a longtime partner at NEA, where she backed Robinhood from seed to IPO), joins Max to get into the nitty gritty of how AI is rewriting venture, distribution
Why a $1.2B exit felt like his biggest failure, and the customer-obsession thesis behind Agency
A $1.2 billion exit is the dream. Elias Torres calls it his biggest failure. The Drift co-founder joins Sophie Buonassisi on GTMnow to unpack why the headline number felt hollow, what he learned in the quiet stretch afterward, and why he jumped straight back in to build Agency, an AI company that runs your entire customer organization.Elias gets honest about identity after the exit, the difference
From DeepMind to 200 Customers in 20 Countries: Building the Execution Layer for Sales | Adam Liska, CEO of Airspeed
The single most expensive sentence in sales is "I'll follow up on that." Adam Liska joins Sophie Buonassisi on GTMnow to break down the "execution gap," the space between knowing what to do in a deal and actually doing it, and why that gap is where most pipeline quietly dies.Adam left DeepMind's Gemini team in 2022, pre-ChatGPT, to build a native revenue execution pla
VC: How Benchmark Picks AI Winners - Max 10 Bets a Year, 5 Partners | Chetan Puttagunta (GP)
Benchmark's Chetan breaks down why the path from $0 to $100M has collapsed from five years to under two, and the one thing that is actually getting harder in the AI era: reaching your first million in revenue. In this VC bonus edition of the GTM Now Podcast, he sits down with Sophie Buonassisi to unpack how AI native companies are compressing 180 day sales cycles into 30 days, why direct sale
Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delany, CEO Primer
LinkedIn CPMs just hit $800. AI is flooding every channel with content. Outbound is dying. So where should B2B marketers actually spend their ad budget right now?Keith Putnam-Delaney, co-founder & CEO of Primer, joins Sophie to break down the complete state of B2B paid advertising, what's broken, what's working, and where the real opportunities are hiding in 2025.What you'll lea
He's Seen 300+ Sales Comp Plans. 90% Make the Same Mistake | Siva Rajamani (Everstage CEO)
Most sales comp plans are quietly broken, and the people running them have no idea. Siva Rajamani, CEO of Everstage, has visibility into 300+ enterprise comp plans, and he says 90% of companies make the same mistakes. In this episode he breaks down what's going wrong, how to spot it, and what a comp plan that actually drives revenue looks like.Siva explains why sales compensation is not a bac
"We Don't Fund Good Companies" : A $1.5B VC Explains Why | Ben Lerer, Lerer Hippeau
Ben Lerer, Managing Partner and Founder of Lerer Hippeau, has built one of New York's most influential early-stage venture firms across nine funds and nearly $1.5B in AUM. In this VC edition of the GTMnow podcast, Ben sits down with Max and Paul to unpack how he actually picks founders, why he wants to be the "worst investor" at his own fund, and the contrarian belief that backing g
How Esper Is Building the Operating System for Government Policy | Maleka Momand
Maleka Momand, co-founder and CEO of Esper, joins Sophie Buonassisi on GTMnow to break down what it actually takes to build and sell software to government. Esper is the operating system for government policy, serving as the system of record for the regulation and internal policy that shapes daily life, from NYPD procedures to nurse practitioner licensing in rural Tennessee.Maleka shares hard-won
How He Built a $250M Company With Zero Employees | Ben Cera, Polsia
One Person, $10M+ ARR, $30M Raised: How Ben Cera Built Polsia (AI Operating System) SoloBen Cera, founder of Polsia, just raised $30M at a $250M valuation while running the entire company alone. His AI agent handles his emails, manages customer support, even led his fundraising calls. This is what a solo founder with an AI operating system looks like at scale.Polsia is an AI operating system that
The $575B AI Bet (Biggest Since the World Wars) and the New Two-Buyer Reality in Software | Tomasz Tunguz, Theory Ventures
AI Infrastructure Spending is Insane: Hyperscalers Betting $575B on the Data Center Race | Tomasz TunguzThis year's data center infrastructure spending will be the 5th largest infrastructure project in history (bigger than everything except railroads and the two world wars). Tomasz Tunguz breaks down what nobody appreciates about the scale of the AI boom.Tomasz Tunguz, General Partner at Theo
SEO Is Not Enough Anymore: Webflow's CEO on the Rise of AEO | Linda Tong
The future of websites isn't a builder problem anymore. It's an agent problem.In this episode of GTMnow, Sophie Buonassisi sits down with Linda Tong, CEO of Webflow, to unpack how the entire web is being rewritten for a world where humans AND AI agents are your audience.Linda breaks down why Webflow is no longer "just a website builder" (it's an agentic web marketing platf
Inside Reevo's $80M Bet to Kill the $10B Frankenstein Stack | David Zhu, Cofounder & CEO
AI is rewriting go-to-market and most companies are still operating with a “Frankenstein stack.”In this episode of GTMnow, we sit down with David, founder & CEO of Reevo, to unpack how AI-native companies will replace legacy GTM systems, why the future of sales teams looks radically different, and how AI agents are becoming the new operating layer for revenue teams.David shares why Reevo staye
VC: "Software Is Basically Worth Zero Now" | Tyler Hogge, Ex-Pelion
Tyler Hogge helped take Divvy from zero to a $2.5B acquisition by Bill.com. Now, as General Partner at Pelion Ventures, he argues that charging for software is dead, per-seat pricing is collapsing, and the next decade of venture-scale companies will be built on outcomes, not subscriptions.In this episode of the GTMnow VC Podcast, Tyler sits down with Max to break down what comes after SaaS pricing
How AI Will Go From Influencing 20% to Making 90% of Your Decisions | Steve Lucas, Boomi CEO
Boomi was founded in the early 2000s by Rick Nucci, acquired by Dell in 2010, and then spun out to Francisco Partners and TPG Capital in 2021. Today it powers 30,000+ enterprise customers globally and moves more data per second than the entire Visa card network, times two. What started as an integration platform has evolved into something bigger: the leading data activation company, purpose-built
Okta's CRO: From $850M in Losses to $760M Profit (The AI Agent Bet) | Jon Addison
Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target.From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround sto
VC: Inside a16z's $1.7B Infrastructure Bet | Jennifer Li, General Partner
Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next.Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else
How Figma Scaled From $2M to IPO | Kyle Parrish (First Sales Hire)
Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG). But the path there was anything but smooth.In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour i
How AI Killed the Discovery Call | Sam Senior, Founder & CEO of TestBox
AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.Sam, Founder and CEO of TestBox, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.If you're a founder, CRO, or AE wondering why your pipeline feels differ
VC: Your First VC Meeting Will Be Agent-to-Agent | Auren Hoffman (Flex Capital)
Auren Hoffman (Flex Capital) joins the GTMnow podcast to share some of the most contrarian takes in tech today, from why AI moats are gone, to why your next VC meeting will be with a bot, to why AI is secretly going to trigger a baby boom.In this episode:- Why Auren runs 500+ AI agents to source deals, and what that means for founders raising capital- The "agent-to-agent" meeting predict
How One Hackathon Took Zapier’s AI Usage From 10% to 97% | CEO of Zapier
Wade Foster is the CEO of Zapier, a company that sits between 7,000+ apps and runs millions of automations every single day. That gives him a front-row seat to how companies are actually adopting AI, not just talking about it.In this episode, Wade breaks down the exact decisions he made at Zapier to go from 10% AI usage to 97% company-wide, why agents and workflows are not the same thing, and what
VC: Investing at Inception in the Age of AI Agents | Ed Sim (Founder & GP, Boldstart)
Ed Sim has been a VC for 30 years. He's backed companies like Clay, Front, BigID, and Snyk. He writes What's Hot in Enterprise IT every single Saturday, 489 weeks in a row. And right now, he says this is the most exciting and terrifying moment he's ever seen in his career.In this episode, Max and Ed break down what's actually happening inside startups and boards right now, why
How Sophos Scales Customer Success for 600,000 Customers in a 24/7 Cyber Threat Environment, with Teresa Anania, SVP of Customer Experience
This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the ol
Bonus Episode: GTMfund Hires a New Partner!
Jason Demant just joined GTMfund as Partner, Head of Networks after 6 years at Foundation Capital where he reviewed over 1,000 emerging manager funds and invested in 100+.In this episode, Max (GP), Paul (GP), and Jason break down what separates the VC firms that survive from the ones that quietly die, why the best founders today are skipping mega funds at pre-seed, and what LPs are excited in abou
Inside ServiceNow’s $10B Go-to-Market Engine with Paul Fipps
NEW: @Paul Fipps (President of Global Customer Operations at @ServiceNow) joins GTMnow to break down how ServiceNow built the customer engine behind $10B+ in revenue and 20%+ growth for five consecutive years.From CIO at Under Armour overseeing a 300 million-member connected fitness ecosystem, to now leading global sales, customer success, field marketing, and partners at one of the most disciplin
What Wins When Anyone Can Build Anything with Brett Queener, Partner at Bonfire Ventures
Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a ge
AI at the Edge: How Armada is Taking Compute Everywhere the Cloud Can't Go | Dan Wright (CEO of Armada)
Dan Wright (Co-founder & CEO of Armada) joins GTMnow to unpack what it actually takes to bring AI infrastructure to the places the cloud was never built to reach.The cloud covers about 30% of the world. The other 70% (think: oil rigs, the Arctic tundra, military ships, remote mines) is where some of the most critical decisions happen, making latency a life-or-death and billions of dollars diff
GTM: Lessons from Figma, Dropbox, and Building Iconic Brands in the Age of AI with Figma’s CMO, Sheila Vashee
NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all.In this conversation, you’ll learn what brand actually means (hint: it
VC: 116 Quarters on Quota and What Every Sales Leader Should Be Tracking, with Bill Binch, Operating Partner at Battery Ventures
Bill Binch (Operating Partner at Battery Ventures) joins GTMnow to share the operational frameworks he's built across 116 quarters on quota, and what actually changes when you move from driving revenue to advising an entire portfolio.Before Battery, Bill was employee #16 at Marketo, where he led sales from zero revenue through IPO and a Vista Equity acquisition. He then served as CRO at Pendo
GTM: BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee
Dan Lee (Co-Founder & CEO of Nooks) joins GTMnow to give a behind the scenes on how Nooks is launching a new Agent Workspace and AI Sequencing layer designed to operate across the full action set of a rep’s day — calls, emails, research, prospecting, and strategy.The conversation explores why top of funnel is changing the fastest, why traditional sequencing tools optimize the “move” but not th
GTM: The End of GTM Sprawl: How HockeyStack is Rebuilding Go-to-Market Around AI, with Co-Founder Emir Atli
Emir Atli (Co-founder and CRO of HockeyStack) joins GTMnow to share how go-to-market is shifting in the AI era — from fragmented tools and GTM sprawl to unified, AI-native platforms built on a single data foundation.Originally known for attribution and market intelligence, HockeyStack is evolving into a central operating system for go-to-market, spanning marketing, sales, and post-sales through AI
VC: How VCs Evaluate Technical Founders (TAM, Moats & Diligence), with Amanda Robson, Founder and GP of Modern Technical Fund
Amanda “Robby” Robson (Founder of Modern Technical Fund) joins GTMnow to break down how she evaluates companies at the very earliest stages and why discipline matters more than ever in today’s market.Amanda has spent over a decade in venture before launching Modern Technical Fund, investing across verticals ranging from security and compliance to developer tools at firms like Norwest and Cowboy Ve
GTM: How Intercom Built the Highest-Performing AI Agent on the Market Using Outcome-Based Pricing with Archana Agrawal, President at Intercom
Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved.Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based p
GTM: Why Most Founders Build the Wrong Company (And Realize It Too Late), with Lou Shipley, Former CEO and Co-Author of Unlikely Entrepreneurs
Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies.Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall.In this conversatio
GTM: Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop
Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events.As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can u
GTM: Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel
Why do so many go-to-market motions fall apart right when a company starts to scale?In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.This is a deep, operator-level conversation about what actually break
VC 3: Investing Philosophy for 2026: What Founders Should Know
Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping th
GTM 174: The 7% Rule: How AI Is Rewriting Customer Success Budgets (From 10% to 7%) with Abbas Haider Ali
Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100.Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Obje
GTM 173: The PLG→Enterprise Playbook: Turning Product Signals into 9-Figure Revenue with Adam Carr
Adam Carr is the Chief Revenue Officer at Apollo, where he’s scaling revenue by layering sales on top of a $150M+ ARR product-led growth engine. Previously, Adam helped scale Miro from a PLG-led company into a global sales organization, contributing to its growth into a $17.5B business. He’s known for building systems-driven GTM teams that turn product signals into durable revenue.Discussed in thi
VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs
Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where
GTM: Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce
Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Des
GTM 171: How to Build a Partner Ecosystem That Sells for You | Brian Weinberger
Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.Discussed in this episodeT
MOMENT: How to Identify Exceptional People Early | Cristina Cordova (Stripe, Notion, Linear)
This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.Cristina Cordova is a
VC 1: Inside the New Exit Economy: IPOs, Secondaries & AI with Meritech’s Alex Clayton
Alex Clayton is one of the clearest minds in growth-stage investing, the person elite founders turn to when the market is noisy and the stakes are high. A General Partner at Meritech Capital, Alex has built a reputation for breaking down complex businesses with uncommon clarity, from his legendary S-1 teardowns to his frameworks on power laws, secondaries, and AI-native growth. Before Meritech, he
GTM 170: 0 Customers → $4B: Inside Snowflake’s GTM Machine with Chris Degnan
Chris Degnan is the former Chief Revenue Officer of Snowflake, where he helped scale the company from pre-product to over $4B in ARR and more than $100B in market cap. Over his 11-year tenure, Chris built Snowflake’s go-to-market engine from the ground up, from personally running the first outbound campaigns to leading a global sales organization through four CEOs and one of the largest software I
GTM 169: How Airbyte Hit $1B: The Open-Source, Community-First Playbook
Michel Tricot is the co-founder and CEO of Airbyte, the open-source data movement platform he launched in 2020. Before Airbyte, Michel led integrations and served as Director of Engineering at LiveRamp, where he scaled the teams and pipelines that synced massive data volumes. He also helped build rideOS as a founding engineer and Director of Engineering. Michel has spent 15+ years in data infrastr
GTM 168: How ZoomInfo Built a $1B RevOps Engine, The Operating Cadence Behind Breakout Growth | Tessa Whittaker
Tessa Whittaker is the VP of Revenue Operations at ZoomInfo, where she leads a 70-person global team powering one of SaaS’s most efficient $1B+ revenue engines. Over the past decade, she’s helped architect the systems, cadence, and AI workflows that underpin how ZoomInfo operates at scale.Tessa is known as one of the most thoughtful operators in tech, bringing structure, clarity, and rigor to how
GTM 167: Competing with Giants: Inside You.com’s Battle Against OpenAI & Google | Peter Grant
Peter Grant is the Chief Revenue Officer at You.com, the AI search and productivity platform reshaping how people find and create information. A veteran GTM leader, Peter has built and scaled revenue engines at some of tech’s most iconic companies — from Siebel Systems to Salesforce to C3.ai — working directly under legends like Tom Siebel and Marc Benioff. Today, he’s leading You.com’s charge aga
MOMENT: ‘I joined Meta at 900, left at 90,000’ — Rick Kelley on Building and Scaling International Sales Teams
This bonus episode dives into how Rick Kelley helped scale Meta’s global sales organization (from 900 employees to 90,000) and the playbook behind building high-performing international teams.Rick Kelley is the former SVP of Gaming and App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization and played a pivotal role in building out Meta’s
GTM 166: SEO → AEO: The Next Big Shift in How People Discover Your Product
Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.Discussed
GTM 165: Vibe prompting, AI fluency, and the new rules of go-to-market | Kieran Flanagan
Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, he’s at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will def
GTM 164: 28th at Stripe → Billions: Cristina Cordova’s GTM Playbook (Linear, Notion)
Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s apply
GTM 163: From $2M to $50M ARR to Unicorn: How Owner Scaled with AI & Talent Density | CRO Kyle Norton
Kyle Norton is the Chief Revenue Officer at Owner, the fast-scaling restaurant SaaS platform valued at over $1B. Since joining from Shopify, Kyle has helped grow the company from $2M to $50M+ in ARR by instilling a high bar for sales talent, building RevOps early, and driving a disciplined go-to-market strategy. A podcast host himself, Kyle shares deep expertise on sales hiring, leadership, and GT
GTM 162: From PLG to Enterprise: How to Layer Sales Without Breaking What Works | Ghazi Masood
Ghazi Masood is the Chief Revenue Officer at Retool, where he leads the go-to-market engine for the low-code developer platform. Previously he served as SVP & GM, Americas at Auth0 after leadership roles at Microsoft, Oracle, Polycom, and Nintex K2, and he advises several high-growth startups on GTM. A field-first operator, Ghazi specializes in layering sales onto product-led motions and build
GTM 161: How to Build a GTM Roadmap (Lessons from Plaid’s $3M → $300M Scale) | Paul Williamson
Paul Williamson is a seasoned go-to-market leader and advisor best known for helping Plaid scale from $3M to $300M ARR. As Head of Revenue, he built and evolved Plaid’s go-to-market roadmap across product-market fit, upmarket expansion, and new verticals. With deep experience aligning GTM with product, he now advises founders on sequencing bets, building forward-compatible roadmaps, and scaling re
GTM 160: The Startup PR Playbook Every Founder Needs: How to Nail Your Launch, Get in the News, and Avoid the Biggest PR Mistakes | Jenny He
Jenny He is the Founder and General Partner at Position Ventures, an early-stage venture fund that backs startups with strategic communications from day one. Previously, Jenny led comms at Square and has since helped hundreds of founders land coverage in top outlets like TechCrunch and Forbes. With deep expertise in positioning, storytelling, and PR, she’s on a mission to help startups craft diffe
GTM 159: Scaling ZoomInfo to over $1B ARR, the Upmarket Playbook, and Launching CoPilot to over $100M Revenue in 6 months | James Roth
James Roth is the Chief Revenue Officer at ZoomInfo, where he oversees a global revenue engine supporting over 37,000 customers and more than $1 billion in ARR. With a background in scaling hypergrowth teams and building enterprise go-to-market machines, James has helped reposition ZoomInfo from a sales tool to the foundational data layer for modern GTM teams. Under his leadership, ZoomInfo launch
GTM 158: From Startup to $4B+ Unicorn: How Vanta Scaled Past $100M ARR and Beat 40+ Competitors | Stevie Case
Stevie Case is the Chief Revenue Officer at Vanta, the $4B leader in trust management and compliance automation. Since joining in 2021, Stevie has scaled the company from sub-$20M ARR to north of $100M, navigated 40+ copycat competitors, rebuilt both pre- and post-sales engines, and led Vanta’s expansion from SMB into enterprise. A former world’s first female pro gamer turned tech sales leader, St
GTM 157: How ClickUp Scaled 17x and Cut CAC 3× — GTM Systems, Building Incrementally and Going from PLG to SLG | Gaurav Agarwal
Gaurav Agarwal is the COO of ClickUp, where he’s helped scale the company 17x in two years and cut CAC by 3x—all while leading across marketing, product, sales, and services. Formerly in banking and product roles, Gaurav brings a rare systems-oriented mindset to growth. He’s known for connecting the dots across GTM, scaling PLG engines, driving incrementality with rigor, and building cultures of e
GTM 156: Revenue Marketing Unpacked: GTM Lessons, AI, and What’s Really Broken in Attribution | John Fernandez
John Fernandez is SVP at Datasite, with a track record as GTM leader at Glia, ContentWise, and Diligent, having scaled teams through IPOs, acquisitions, and $1.4B in equity events. At Glia, John pioneered revenue marketing’s impact, driving 71% of pipeline and 60% of new business revenue from marketing. Connect with him for real-world GTM lessons, scaling playbooks, and unique frameworks for align
GTM 155: How to Build a GTM Motion from Scratch — Using AI, Community, and Data as a Moat | Erica Anderman
Erica Anderman is the co-founder and COO of Foodini, an AI-powered platform solving food allergy and dietary transparency through data infrastructure. With over 15 years of go-to-market experience across foodtech and vertical SaaS, Erica has led revenue at companies like Slice, Seated, and Odeko, and held roles across sales, customer success, partnerships, and RevOps. She began her career in door-
MOMENT: The Next Digital Revolution: You Optimized for Humans, Now You Have to Optimize for AI | with Mike Walrath (CEO of Yext)
This bonus episode explores one of the most important shifts happening in go-to-market right now: the move from optimizing for humans to optimizing for AI.Mike Walrath, CEO of Yext and former founder of Right Media (acquired by Yahoo for $850M), shares why this change is as big — or bigger — than the first wave of digital transformation. You’ll learn how AI agents are changing how customers discov
GTM 154: How AI is Reshaping Sales Tech | Lessons from Building Sales Cloud, Sales Navigator and now an AI-Native Startup
Doug Camplejohn is a serial entrepreneur and seasoned executive with extensive experience in B2B SaaS and go-to-market strategies. He has previously held leadership positions at major tech companies including LinkedIn, Salesforce, and Apple before founding Coffee, an AI-first CRM platform.Discussed in this Episode:AI-powered CRM and sales automationGo-to-market stack optimization and simplificatio
GTM 153: Building Technical Growth Machines & Signal-Based Selling with Austin Hughes
Austin Hughes is the founder and CEO of Unify, a platform helping high-growth teams turn buying signals into pipeline. Previously, Austin led the growth team at Ramp, where he scaled the org from 1 to 25+ and pioneered a product-led, experiment-driven GTM approach. With a background in investment banking and venture capital, Austin brings a uniquely analytical and first-principles mindset to moder
GTM 152: What’s Actually Working in GTM Right Now: Lessons from Centari, Atrix AI, & Gaiia
What’s actually working in go-to-market right now? In this live panel from the GTM Fund AGM, three early-stage leaders from three exceptional companies—Centari, Atrix AI, and Gaiia—break down how they’re closing enterprise deals in some of the most challenging verticals: legal, pharma, and telecom. From viral LinkedIn content and founder-led dinners to the now-infamous "donut drop" strat
GTM 151: How to Scale Vertical SaaS in 2025 | Dennis Lyandres (Ex-CRO, Procore)
Dennis Lyandres is an Advisor with ICONIQ and a Board Member of Speedchain and CaptivateIQ. Dennis amassed incredible insights through his experience as the Chief Revenue Officer of Procore, where he helped grow the company from $10M to $900M+ in revenue and guided it through a successful IPO. At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. He’s now an invest
GTM 150: 80% of Exec Roles Aren’t Posted, Here's How to Land Them Anyway with Andy Mowat
Andy Mowat is the Co-Founder of Whispered, and is responsible for building incredible RevOps and GTM systems at unicorns like Upwork, Box, and Culture Amp. With over two decades of experience leading marketing ops, sales ops, and go-to-market infrastructure, Andy is a true pioneer of modern RevOps. Today, he’s building tools to help tech executives collaborate on company insights, search strategi
GTM 149: How to Scale International Sales Teams with Rick Kelley
Rick Kelley is the former SVP of Gaming & App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization & played a pivotal role in building out Meta’s go-to-market teams across North America & EMEA. Over his 15-year career at Meta, Rick was instrumental in driving international expansion, especially across Europe, the Middle East, &a
GTM 148: Winning Every Tech Shift from a 3X Founder (From Internet to AI)
Sean Whiteley is a three-time founder and the Co-Founder of Qualified, the AI pipeline automation platform purpose-built for inbound GTM teams. Previously, he founded GetFeedback (acquired by Campaign Monitor) and Kieden (acquired by Salesforce), where he also served as SVP & GM. With over two decades at the forefront of tech’s biggest transformations—from on-prem to cloud to AI—Sean offers a
GTM 147: RevOps Is a Hidden Growth Engine with Navin Persaud, VP of RevOps at 1Password
Navin Persaud is the VP of Revenue Operations at 1Password, where he leads a 30+ person team supporting a GTM org of 450+. With over 20 years of experience across RevOps, SalesOps, and MarketingOps, including time at IBM and high-growth SaaS companies, Navin has built a reputation as one of the sharpest operators in the game. He’s known for building scalable systems, ruthless prioritization, and a
GTM 146: The Future of Search, AI, and Digital Presence with Mike Walrath, CEO of Yext
Mike Walrath is the CEO and Chairman of Yext, a publicly traded digital presence platform that helps businesses manage and synchronize their digital presence across search engines, maps, apps, and voice assistants by ensuring that information like locations, services, FAQs, and brand content appears accurately and consistently wherever customers search.He also co-founded WGI Group, LLC, to provide
GTM 145: What Happens When a CRO Owns the Entire Customer Journey, How to Build a Unified GTM Engine | Marcy Campbell
Marcy Campbell is the Chief Revenue Officer at AppFolio, where she leads sales and client services with a focus on delivering unified, end-to-end customer experiences. With over 30 years of experience scaling revenue teams across FinTech, SaaS, cloud computing, and communications, Marcy has held executive roles at Boomi and PayPal—where she led an 800+ person global team. Her deep expertise in ali
GTM 144: How AI is Rewriting Product and GTM Playbooks | with Oji Udezue (CPO - Typeform, Calendly)
Oji Udezue was most recently Chief Product Officer at Typeform, where he led product strategy across the company’s growing suite of tools. Previously, he was CPO at Calendly, where he helped scale one of the most beloved PLG tools in the market. Before that, he was Head of Product for Creation and Conversation at Twitter, leading core features like Tweets, DMs, and Spaces. At Atlassian, he led all
GTM 143: Why Most AI Messaging Fails and How to Actually Stand Out in a Crowded Market | Harmony Anderson
Harmony Anderson is an entrepreneurial marketing leader with deep expertise in building global GTM strategies at growth startups. She is currently the VP of Growth and Marketing at Superhuman, the most productive email app ever made for teams. She has also led high-performing teams at Armada, Engine, Outreach, and ThousandEyes.She is deeply passionate about creating world-class marketing campaigns
GTM 142: Why Most B2B Marketing Fails (And How to Fix It) with Udi Ledergor
Udi Ledergor served as CMO during Gong’s rise from new SaaS startup to industry dominance. By building a playful, human-centric brand with a lighthearted tone, he captured buyers’ attention and dollars and turned them into raving fans. He helped Gong go from zero to hundreds of millions in revenue, while achieving a multi-billion-dollar valuation. His book Courageous Marketing is officially out an
GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry
Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade.Discussed in this Episode:How to turn coworkers into
GTM 140: How Microsoft Scaled from $600M to $5B: The Enterprise Playbook with Hayden Stafford
Hayden Stafford is the President and Chief Revenue Officer (CRO) at Seismic, where he oversees the global go-to-market (GTM) organization, including pre-sales, sales, customer success, services, partners, and more. Prior to joining Seismic, he served as President of Global Field Operations at Pegasystems. Before that, Hayden was Corporate Vice President at Microsoft, leading Global Business Applic
GTM 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith
Ray Smith is the VP of AI Agents at Microsoft. Previously, he was the Global VP of Product for SAP, CRM and Sales Cloud. Before that, he was the CEO and Co-Founder of DataHug, which was acquired by Calidus Cloud in 2016. Ray breaks down why the rise of AI agents is a tectonic shift, how businesses are already seeing ROI, and what it means for SaaS, team structure, and go-to-market strategies. He a
GTM 138: The AI Advantage, Solving Sales & Marketing Alignment for Better GTM Execution with Jaleh Rezaei
Jaleh Rezaei is the CEO & Co-founder of Mutiny, a company reimagining the B2B buying experience by transforming transactional relationships into meaningful connections through AI-powered personalization. Mutiny helps enterprises restore the human element in modern buying at scale, and is used by some of the fastest growing companies in the world including Amplitude, Snowflake and Qualtrics. Th
