The GTMnow Podcast
by GTMnow
The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down. This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more. Visit gtmnow.com for more details and to sign up for our newsletter and o
Episodes
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Lambda: From Convincing Buyers to Use GPUs to an 11-Figure Deal | Robert Brooks, CCO
Robert Brooks has been selling compute at Lambda since 2018, back when he had to convince buyers to use GPUs at all. Today he’s Lambda’s Chief Commercial Officer and closes 11-figure contracts. He’s also a GTMfund LP. In this live conversation from the GTMfund AGM, Robert shares a close-up view…
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Inside Exa’s Run to $100M ARR: Building Google for AI Agents | Marcus Holm (CRO, Exa)
Exa just passed $100M ARR, growing nearly 10x per year for almost three years. Marcus Holm, Chief Revenue Officer there after serving as President at LaunchDarkly, breaks down how a company building “what Google is for humans, but for AI agents” scaled that fast. Marcus explains why he describes...
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How Datarails Grew 30x in 5 Years (90% Outbound → 90% Inbound) | Aviv Canaani (CRO & CMO)
Today marks Aviv Canaani’s 5-year anniversary at Datarails! When he first joined Datarails five years ago, the company was 90% outbound, with analysts emailing inbound leads to SDRs once a week. Today it’s 90% inbound, 30x bigger, $70M Series C, and The Information named it the #1 startup of the...
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The ex-engineer who says sales beats product | George Kurdin (CEO, Monk)
George was a professional poker player, then CEO of a company that sold to Logitech for around $100M, and now he’s the CEO of Monk, an AI company automating accounts receivable. Monk is an API company solving the other side of the ledger from Ramp: getting B2B invoices paid. George gets candid...
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Legora's CRO: $3.5M to $200M+ ARR, the Fastest Direct Sales Motion | Patrick Forquer
Legora went from $3.5M to over $100M in revenue in about a year, the fastest any company has ever scaled a direct-sales motion from zero to $100M. Then, they doubled revenue in less than 6 months and hit $200M ARR. Patrick spent seven years at Braze, from the early days through IPO, before…
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Lessons from building 113 AI agents and reinventing a GTM function with AI | Meagan (CMO, Samsara)
The CMO of Samsara joins GTMnow to walk through exactly how she ran an AI transformation inside a public company, from a 2.5 week boot camp to 113 agents in production, all while keeping headcount flat and pushing pipeline and revenue up. Meagan has led teams through platform shifts before (PLG,...
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Inside LinkedIn: buyer behavior, how to social sell, why warm intros get 3x the response, why only 45% of sellers are seen as trustworthy and the 4 behaviors that separate top sellers | Catherine Flynn (LinkedIn Sales Navigator)
Information has never been more abundant, and trust has never been harder to earn. That's the tension at the heart of LinkedIn's new research, "The Trust Advantage," and Catherine, who leads marketing for LinkedIn's Sales Solutions business (Sales Navigator), joins Sophie Buonassisi on GTMnow to...
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Why More AI Won't Grow Your Revenue (and What Will) | Loreal Lynch (CMO, Nooks)
The CMO of Nooks (and former CMO of Jasper) joins GTMnow to explain why buying more agents won't grow revenue unless you rebuild the process underneath, and what the human-plus-agent revenue team truly looks like. Loreal has had a front-row seat to two AI waves: first at Jasper, where AI reshaped...
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Building an AI-Era Sales Machine | Chris McDonough (VP Sales, Campfire)
Chris McDonough has joined four companies right before they exploded. At the first, Motive, he was employee 40 and watched revenue go from $800K to $30M in about 100 days. The VP of Sales at Campfire joins Sophie Buonassisi on GTMnow to break down what he learned riding hypergrowth over and over,...
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Inside Electric's AI Relaunch, from a 3X Founder | Ryan Denehy (Founder & CEO, Electric)
The founder and CEO of Electric, Ryan Denehy joins GTMnow to explain why and how he rebuilt Electric as an AI-native software company. Ryan gets specific on why he split the business in half, how the pivot forced a total change in distribution (from direct sales to embedded channel partnerships...
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What the Top 1% of Sellers Do Differently | Ross Rich (CEO, Accord)
Ross Rich is the co-founder and CEO of Accord and spent five years leading go-to-market and partnerships at Stripe. He talks to hundreds of CROs and serves thousands of reps, so he has an unusually clear view of what the top performers actually do differently. His starting point: roughly the top...
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Will Salesforce Win the AI Era Like It Won Cloud? | Kris Billmaier
Is Salesforce the dominant player in the AI platform shift, or the incumbent about to be disrupted? Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products, sat down with Sophie Buonassisi at Salesforce Tower to answer that directly. Kris runs the business behind Sales Cloud's 26-year...
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Inside Deel's $1M → $1.5B Sales Machine | Chris Lee
Chris Lee joined Deel at $1M in revenue. Now, it just hit $1.5B. He joined GTMnow to walk through the pivotal decisions behind that run, including the ones he's never discussed publicly. Chris (Head of Sales, Americas at Deel) breaks down the "five-star sales experience" framework he built by...
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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...
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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…
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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...
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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...
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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...
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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...
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Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delaney, 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…
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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...
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"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...
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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…
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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) Solo Ben 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…
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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 Tunguz This 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...
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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...
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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…
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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…
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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...
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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...
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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…
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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...
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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...
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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…
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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…
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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…
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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...
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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...
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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…
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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…
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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…
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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…
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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...
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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…
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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…
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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…
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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,...
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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...
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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,...
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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...
About this show
The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.
This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more.
Visit gtmnow.com for more details and to sign up for our newsletter and o
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