Podcast
The GTMnow Podcast
Hosted by GTMnow · EN
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 other content resources.
56episodes
Episodes
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Inside Merge: The $75M Bet on Open Source AI (Powering OpenAI, Netflix & Uber) | Shensi Ding, CEO
6d ago00:47:18Tap to summarizeThe 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-serve motion back on top (20,000+ self-serve orgs, 400+ enterprise customers), how forward-deployed engineers turned a 1% edge case into 5 to 10x usage growth, and why she rebuilt marketing to run like an engineering team. She also gets candid on founder-led sales, the mercenaries-versus-missionaries hiring trap, the open-source model shift and the China question, and why every founder who started pre-AI should build one product 0-to-1 themselves.What you'll learn:- Why she reversed the standard GTM playbook (enterprise first, then PLG) and how to run both motions at once- How forward-deployed engineers close the 1% edge case that unlocks 5 to 10x enterprise usage- Why marketing now runs like an engineering function at Merge, and how it took her from 1 to 2 dinners a quarter to 3 to 5 a month- Why product got fast and go-to-market became the new bottleneck- How to know when to hire your first salesperson (hint: you should be "dying" first)- The mercenaries-vs-missionaries test, and the "anti-sell" she uses in hiring- The 2026 shift away from "token-maxing," and how model routing cuts AI spend- The truth about open-source (often Chinese) models: where they're built vs. where your data actually lives- Why founders who started pre-AI should build one product 0-to-1 to understand what's now possibleChapters:00:00 Intro01:14 What Merge does: products, workforce, and three core offerings02:05 Agent Handler, Gateway, and the new Embedded Routing Stack04:52 The 2026 shift away from "token-maxing"07:29 Open-source models, the China question, and where data really lives10:14 How Merge works with open-source model providers12:00 What she's learned as a first-time founder: get over your ego13:22 Reversing the GTM playbook: enterprise-first, then PLG15:50 Running both motions: 20,000+ self-serve, 400+ enterprise17:31 Why buyer behavior moved to Twitter and brand19:06 Founder-led sales, and what a real sales process taught her22:27 When to hire your first salesperson23:49 Forward-deployed engineers and 5 to 10x usage growth27:00 Keeping go-to-market up to speed with product28:33 Rebuilding marketing as an engineering function30:45 The dinner agent: 1 to 2 a quarter to 3 to 5 a month31:24 How AI buying reshaped the marketing org33:54 Maintaining agents: prompts over legacy builders35:02 Mercenaries vs. missionaries, and the "anti-sell"40:25 The market view: from hostility to collaboration42:06 Is a valuation reckoning coming?43:07 Why she stayed hands-on building Agent Handler and Gateway45:18 What's next: training your own models off open-source46:52 Where to find Shensi and MergeConnect with Shensi Ding:LinkedIn: https://www.linkedin.com/in/shensiding/X: https://x.com/shensiMerge: https://merge.devHost: Sophie Buonassisi, SVP at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaAbout the guest: Shensi Ding is the co-founder and CEO of Merge, a unified API platform that now spans product integrations, agent tooling, and LLM routing/governance. Merge powers companies including OpenAI, Perplexity, Netflix, Uber, and Mistral, and enterprise customers like Mastercard, JP Morgan, and Amex. The company has raised $75M from Accel and NEA.Thank you to our sponsor:Primer unlocks B2C ad channels for B2B marketers with precision targeting and next-gen measurement. GTMnow Network exclusive offer: Extended 45 day trial and 15% off with code GTM15 - just apply the code when you go to upgrade from the free trial.See who’s really in your funnel: sayprimer.comAbout GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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The Blueprint for a High-Performing Sales Team | Brian Le, Notion
3w ago00:45:54Tap to summarizeAre 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 revenue operations. If you are a founder, revenue leader, or sales professional, this breakdown covers everything from structuring pay mix to identifying the earliest signs of comp plan degradation. You will even hear what it takes for top AEs to pull in upwards of $1 million in a single quarter.In this episode, we cover:00:00 Intro01:15 Brian Le's journey through Salesforce, Carta, and Notion04:33 Why sales comp is the operating system for go-to-market07:07 Phase 1: Building a scalable comp foundation at Notion13:50 Transitioning from seat-based to usage-based pricing models18:15 The 3 core pillars of a successful sales commission plan22:09 Early warning signs your quota and comp structures are breaking31:41 The real cost of losing sales reps over bad commission payouts39:35 How to structure compensation for your first early-stage sales hires42:39 Will AI agents replace SDRs and sales compensation?Connect with Brian Le, :LinkedIn: https://www.linkedin.com/in/brianhoangle/Host: Sophie Buonassisi, SVP at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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VC: How a 2-Person Fund Runs Like a Startup (Memos, KPIs, R&D) | Vanessa Larco, Premise (ex-NEA)
3w ago00:48:50Tap to summarize"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, and the entire go-to-market playbook.She makes the case for why "it's just a wrapper" got a lot of VCs in trouble, why she only backs technical founding teams, and why the old GTM playbook is breaking fastest exactly where you'd least expect it. She also opens up about leaving a big platform to build a two-person fund from a blank canvas, and why she treats the fund itself like a startup.What you'll learn:- The "OpenAI won't kill it" framework for spotting durable AI companies (and why not everything OpenAI ships actually wins)- Why the "it's just a wrapper" dismissal cost VCs real deals, and the kayak/AWS parallels that explain why- Why Premise only backs technical founding teams, and the shipping speed that becomes the real early moat- How the old go-to-market playbook is breaking, especially in DevTools, and what replaces it- Why someone on the founding team has to "nerd out" on distribution, and why no-playbook moments are where you growth hack- How to run a conviction-based investment committee, and why big funds drift toward consensus whether they like it or not- Why running a fund is just running a startup: fundraising, product, and customer success by another name- The unanswered question Vanessa keeps circling: how to give experienced GTM talent space to rewrite the playbookChapters:00:00 Intro & OpenAI Moats01:12 GTMnow Intro01:51 Technical vs. Non-Technical AI Founders04:37 The Bottleneck of Hiring AI Talent05:15 Do Old Moats Still Exist?06:36 Cloud Era Lessons vs. Today's AI Layer09:18 The Shift to the Distribution Era11:38 Interview: Vanessa Larco (Premise VC)12:40 Companies OpenAI Won't Kill13:37 Consumer Habits vs. Enterprise AI15:05 Moving Beyond the "Wrapper" Stigma17:39 Thesis Building vs. Founder Curiosities20:11 Sourcing & The "Surreal" Community22:26 Learnings From NEA & Lightspeed24:06 Rethinking the Investment Memo26:43 Consensus vs. Conviction Investing31:26 Running a VC Fund Like a Startup35:04 Building Internal Automation Tools37:35 Distribution Moats & DevTools39:38 Sourcing New GTM Playbooks41:12 Parallel to the AWS Boom43:55 Human Psychology vs. AI Tools47:06 SF's Best Cookie Spots48:32 OutroConnect with Vanessa Larco:About the guest: Vanessa Larco is the founder and GP at Premise. Previously a partner at NEA, she backed consumer and fintech companies including Robinhood from seed through IPO. She started her career in product and engineering, was a computer science undergrad, and founded and sold her own startup before moving into venture.Connect with Max: https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschuler/Connect with Vanessa:https://www.linkedin.com/in/vanessalarco/https://x.com/veelarcoAbout GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. This is the VC bonus series, where we host VCs and get into the VC ecosystem.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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Why a $1.2B exit felt like his biggest failure, and the customer-obsession thesis behind Agency
4w ago00:52:51Tap to summarizeA $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 between chasing a title and building something enduring, and the operating thesis behind Agency: a billion-dollar company with fewer than 100 people, where 80 to 90% of the team are engineers and everyone talks to customers. He also gets into distribution as the hardest problem in the AI era, why he only takes money from investors who lead with value (Pat Grady and Brian Halligan back the company), and the two decades he's spent building alongside David Cancel.What you'll learn:- Why a $1.2B exit can still feel like a failure, and what "enduring" actually means- How to rebuild your identity when the title goes away- The Agency thesis: $1B with under 100 people, and how AI agents make it possible- Why Elias runs the whole company on Agency itself, with no CRM- Why sales may be the last role AI eliminates, and what that means for GTM- How to spot investors who lead with value instead of a pitch deck- Why distribution, not product, is the hardest problem in the AI era- What 20+ years building with David Cancel (Performable, HubSpot, Drift) taught him about partnershipChapters:00:00 Intro02:25 Time off, slowing down, and losing the title04:00 The inflection point and what comes after a big exit07:00 What Agency is and the problem it solves11:00 Why he brought people he's known for years11:40 Investors who lead with value (Pat Grady and Brian Halligan)17:30 Building with David Cancel for 20+ years23:00 The bold claim: $1B with under 100 people26:00 The go-to-market motion behind it28:30 "Sales is the last role AI will eliminate"36:00 High-agency people and how Agency runs itself42:00 Building distribution in the AI era51:00 Where to find Elias and AgencyAbout the guest: Elias Torres is the founder and CEO of Agency, an AI company that provides agents to run a company's customer organization. He previously co-founded Drift (acquired in a $1.2B deal) and held senior roles at HubSpot and Performable, building alongside David Cancel for over two decades. Agency is backed by Pat Grady (Sequoia) and Brian Halligan.Connect with Elias Torres:LinkedIn: https://www.linkedin.com/in/eliast/X: https://x.com/eliastHost: Sophie Buonassisi, SVP at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaAbout GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
Transcribe →From DeepMind to 200 Customers in 20 Countries: Building the Execution Layer for Sales | Adam Liska, CEO of Airspeed
Jun 2500:32:22Tap to summarizeThe 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 platform now serving 200 customers across 20 countries (recently rebranded and fresh off a $20M Series A). In this conversation, he gets specific on what is actually changing in the sales role, what should be automated, and why he thinks this is about to be the golden age for sales reps.What you'll learn:- Why "I'll follow up on that" is the most expensive promise in revenue, and how the execution gap compounds from rep to manager to CRO- What parts of the rep workflow to automate now (research, CRM updates, business cases, follow-ups) and what stays human- Why AI is squeezing middle management, not reps, and flattening GTM orgs- How per-rep coaching changes when every call is recorded, shared, and analyzed for patterns- The "corrective action" approach to coaching deals on the job, in real time- How to sell globally when borders disappear but local-language talent still matters- Why in-person events drove 70% of early pipeline, and how that compounds with cold calling- How to keep your team at the AI frontier by never locking into a single model- Adam's #1 piece of advice for first-time founders (hint: it starts with your co-founder)Chapters:00:00 Why AI won't replace sales reps00:22 Leaving DeepMind's Gemini team pre-ChatGPT01:18 What airspeed does and the "execution gap"02:07 "I'll follow up on that": the most expensive promise in sales03:28 The $20M Series A and the rebrand from Glyphic05:30 Why walk away from frontier AI research at DeepMind07:17 Leading when the frontier models keep changing08:39 Buy vs. build, and keeping customers at the AI frontier11:03 Landing the first 200 customers across 20 countries12:41 Advice for first-time founders14:04 Selling globally and what AI changes about language17:07 What the sales rep role looks like in an AI-first world19:24 How reps and leaders should start automating today20:51 The channels driving results right now22:41 How AI makes per-rep coaching actually work25:14 Building an execution-first culture27:10 The DeepMind departure story28:51 Building in London vs. selling in the US30:43 Adam's favorite AI use case as a busy CEO31:26 The biggest misconception about AI in salesHost: Sophie Buonassisi, SVP at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaGuest: Adam Liska, Co-founder and CEO at AirspeedX: https://x.com/adliskaLinkedIn: https://www.linkedin.com/in/adliska/About the guest: Adam is the co-founder and CEO of Airspeed (formerly glyph), a native revenue execution platform that closes the gap between knowing what to do in a deal and executing on it. Before founding the company, he worked at DeepMind on the team that became Gemini. About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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VC: How Benchmark Picks AI Winners - Max 10 Bets a Year, 5 Partners | Chetan Puttagunta (GP)
Jun 2400:59:24Tap to summarizeBenchmark'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 sales is here to stay, and how value is shifting away from code toward the last mile of customer service.Using Legora (legal AI) and Manus as case studies, Chetan explains how Benchmark builds conviction fast, why the marginal cost of code trending to zero changes everything, and what separates the founders who win this window from the ones who miss it.What you'll learn:- Why the first $1M now takes longer than the next $99M in the AI era- How top AI startups compress a 180 day sales cycle into 30 days- The "trusted vendor" playbook for breaking incumbent distribution advantages- Why Legora embedded inside a law firm for a year before launching- How a magical demo plus a tightly scoped pilot collapses six month deals- Why value is moving from the product build to the service and outcome- What Benchmark actually looks for: technical insight that creates demand pull- Why direct sales and forward deployed engineers are exploding in AI- How buying one AI app triggers an enterprise to buy 100 moreChapters: 00:00 Intro01:13 Why Max + Paul were furious taking notes on this one02:10 Benchmark's $2B growth fund and the changing strategy04:57 POC to trial and the power of direct sales in AI11:33 Meeting Max early: $0 to $100M in 18 months15:05 Manus: 0 to $100M in eight months through PLG17:10 Will the AI native window close?19:09 Sizing the window: $40B software vs $1T services in legal21:50 How Benchmark picks the winners25:31 Turning a 180 day sales cycle into 30 days30:45 The Legora deep dive: research, pilots, legal engineers41:46 Why $0 to $100M keeps getting faster42:29 The harder problem: getting to your first $1M44:04 When code goes to zero, what do customers pay for?48:46 Sales led vs PLG in the AI era51:49 How to spot the right founder55:18 What company Chetan wishes someone would build56:48 Investors founders should follow57:40 Working with Jack Altman at BenchmarkConnect with Chetan Puttagunta: General Partner at BenchmarkTwitter/X: https://x.com/chetanpLinkedIn: https://www.linkedin.com/in/chetanputtagunta/Host: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/About the GTMnow Podcast:GTMnow is the media brand of GTMfund, sharing the tactics and strategies behind how the best companies go to market. The VC series brings on top investors to break down what is actually working in go to market today.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delany, CEO Primer
Jun 1700:45:43Tap to summarizeLinkedIn 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 learn:- Why LinkedIn & Google search are hitting a ceiling (and what to do instead)- How to get 80% match rates on Meta and 70% on Reddit for B2B audiences- The only moat competitors can't copy: your targeting- Why you need to feed CRM conversion data back to ad platforms- Holdout groups, attribution, and what actually proves paid ROI- The truth about ads in LLMs (ChatGPT, Perplexity, Grok)- B2B influencer marketing: the most undervalued tactic right now- Founder lessons from 6 years and 3 pivots building PrimerChapters:0:00 – The paid advertising crisis no one's talking about2:40 – AI's real impact on ad costs4:06 – Google Search & AI Overviews: what still works5:04 – LinkedIn CPMs: $20 to $800 in 18 months6:39 – Why B2B brands need to be on Meta, Reddit & Instagram7:01 – What Primer does (80% match rates explained)9:29 – The device fragmentation problem & attribution11:16 – Holdout groups: the statistically proven approach13:30 – Which channel to start with (and minimum spend)22:18 – Paid ad creative: feed the algorithm with variants25:14 – B2B influencer marketing & thought leadership ads30:59 – Why you MUST push CRM data back into ad platforms33:31 – Ads in ChatGPT & LLMs: what's coming35:53 – Founder lessons, mental health & iterationConnect with Keith Putnam-Delaney: Co-founder, CEO of PrimerTwitter/X: https://x.com/kcpdelaneyLinkedIn: https://www.linkedin.com/in/keithputnamdelaney/Host: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/About Keith Putnam-Delaney:Keith is the co-founder and CEO of Primer (https://www.sayprimer.com/), a B2B paid advertising targeting layer that helps brands unlock high match rates on Meta, Google, Reddit, and beyond. Former brand marketer turned data-driven growth leader.GTMnow is the media brand of GTMfund, sharing go-to-market insights from the top 1% of revenue operators.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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He's Seen 300+ Sales Comp Plans. 90% Make the Same Mistake | Siva Rajamani (Everstage CEO)
Jun 1500:57:22Tap to summarizeMost 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 back office cost center but the single biggest lever in your go-to-market strategy. It's the glue between what a company intends and what reps actually do. If your reps aren't doing what you want, the answer isn't in a 1-on-1. It's in your comp plan.We get into the over-complication trap, the hidden math that makes reps refuse your best deals, the base-to-variable ratios that actually work, why your top reps should out-earn almost everyone, and how AI is about to blow open the gap between your best and average sellers.Chapters:00:00 Intro00:30 Siva's RevOps background at Freshworks04:00 Scaling RevOps from 1 to 2504:50 Why he left to build Everstage06:30 Why incentives drive revenue, not tools08:00 Comp as the glue between intent and action10:30 The 1 to 2 mistakes almost every team makes12:00 "If your comp plan needs FAQs, it's a tax code"14:00 The 60-second test for a broken plan15:30 Designing comp to retain top talent16:50 How AI widens the gap between top and average reps18:00 The $1M sales rep is coming19:30 Why optimizing for top earners is better on margins21:30 Quota to OTE ratios that actually work23:00 Base vs variable: the 50/50 rule and exceptions24:00 What Everstage does and who it serves25:30 How Everstage structures its own comp plan28:00 The rise of the revenue architect48:00 CPQ and connecting margin to commissions50:30 When should reps earn commission in the deal cycle52:30 Six month vs twelve month comp cycles54:30 The most a sales rep has ever made55:20 Where to find SivaConnect with Siva Rajamani: Co-founder, CEO of EverstageTwitter/X: https://x.com/siva_rajamaniLinkedIn: https://www.linkedin.com/in/sivasrajamani/Host: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ABOUT GTMnowGTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/Subscribe for more conversations with the operators and founders behind today's best go-to-market teams.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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"We Don't Fund Good Companies" : A $1.5B VC Explains Why | Ben Lerer, Lerer Hippeau
Jun 900:55:46Tap to summarizeBen 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 good, sensible businesses is a mistake.Ben got his start in media, building Thrillist before it merged into Group Nine, then turned those relationships and that operator empathy into a venture career writing early checks into companies like Warby Parker and Casper. He shares what's changed about winning deals in a more competitive, sharp-elbowed market, how Lerer Hippeau runs its investment committee on conviction rather than consensus, and the process failure behind passing on Peloton.We also get into the debate every investor is wrestling with right now: the crazy, fast-moving AI-native founder versus the second or third-time operator with deep domain expertise, and why the answer is rarely a silver bullet.A real venture-nerd conversation on firm building, IC decision-making, founder selection, and what it takes to chase the power law.Topics covered:- The "worst investor at my own fund" philosophy- Conviction vs. consensus in the investment committee- Why Lerer Hippeau funds "crazy" founders, not good companies- The Peloton miss and what it revealed about process- From Thrillist and digital media to venture capital- AI-native founders vs. domain experts- How to win competitive deals as a smaller firmChapters:00:00 Intro00:52 Max and Paul on the episode: IC process and founder selection14:36 Conversation with Ben Lerer begins15:02 Nine funds, $1.5B AUM, and the early-stage strategy23:00 From Thrillist to venture: the media springboard28:00 What's changed in picking founders and winning deals33:00 How the investment committee grew and evolved37:40 The "magic" deal and chasing high-conviction bets50:43 Why Ben wants to be the worst investor at his fund53:00 Funding crazy people, not good companies51:35 Yankees or Mets?Connect with Ben Lerer: https://x.com/BenjLererLinkedIn: https://www.linkedin.com/in/benlerer/Connect with Max: https://x.com/hackitmaxlinkedin.com/in/maxaltschulerListen on Apple and Spotify, and subscribe for more GTMnow VC editions.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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How Esper Is Building the Operating System for Government Policy | Maleka Momand
Jun 400:31:09Tap to summarizeMaleka 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 lessons from 8 years in GovTech: why winning trust matters more than winning business, why professional services are a moat (not a cost center), and how Esper turns slow, paper-based policy processes into live digital workflows. She also covers the DOGE effect across red and blue states, why enterprise SaaS still has defensible moats in the age of AI, and her advice to founders entering regulated markets.Whether you're a founder, GTM leader, or operator selling into complex, slow-moving markets, this conversation is packed with practical playbooks on trust, go-to-market, and building durable enterprise software.Chapters:00:00 Intro00:44 Two types of government policy (regulation vs internal)02:06 The NYPD 3,000-page policy problem03:23 Digitizing a paper-based, 20-person workflow04:12 Why policy is infrastructure05:23 Real impact: Tennessee healthcare & Arkansas hunting licenses07:45 Esper's ideal customer: complexity, catalyst, volume08:18 Going to market in GovTech (and why it's slow)10:16 Advice for founders entering GovTech: win trust first11:27 Why professional services are a moat12:38 In-house vs third-party services13:49 What DOGE actually looks like on the ground15:11 Is DOGE a tailwind for Esper?16:36 The new funding round & enterprise SaaS in the age of AI19:13 From VC to founder: why Maleka made the shift22:10 Advice for founders: read fiction, not productivity books24:14 AI, data quality, and the problem with vibe coding26:43 How Esper uses AI internally (meet "Poly")27:27 Building a high-agency culture while scaling29:00 Closing thoughtsConnect with Maleka Momand: Co-founder, CEO of EsperTwitter/X: @MalekaMomand LinkedIn: linkedin.com/in/malekamomandHost: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ABOUT GTMnowGTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech.#GovTech #GoToMarket #EnterpriseSaaS #StartupAdvice #GTM #SaaS #FounderAdvice #GovernmentTechnology #PolicyTech #AIThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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