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 experimentation, ownership, and speed.Discussed in this episodeWhy growth is more about systems than marketingHow ClickUp scaled 17x while reducing CAC by 3xThe cultural shifts required to align GTM teamsIncrementality testing vs. attribution modelingBuilding a true sales motion on top of PLGInput KPIs as a driver of experimentation speedHow ClickUp is using AI across marketing and salesThe concept of GTM as demand creation vs. harvestingEpisode Highlights00:00 — Everyone is doing all the work—but you're winning by chance, not by design02:01 — Gaurav on seeing growth as a systems function, not just marketing13:33 — Culture alone delivered roughly half of the 3× CAC reduction at ClickUp15:53 — Gaurav defines incrementality testing vs. flawed attribution models29:27 — Setting input KPIs so squads deliver a “win every week” keeps momentum high32:53 — AI is being embedded across PLG + GTM workflows—from content briefs to deal signalsRecommended BooksShareholder Letters by Jeff Bezos ReferencedClickUp:https://clickup.com/• Gong: https://www.gong.io/• Netflix: https://www.netflix.com/• Robinhood: https://robinhood.com/Guest Links (Gaurav Agarwal):LinkedIn:https://www.linkedin.com/in/gauravragarwal/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTMnow Podcast (on all major directories): https://gtmnow.com/tag/podcast/Thanks to our Sponsor: QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.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.
--------
52:37
--------
52:37
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 aligning marketing with revenue.Discussed in this Episode:How to architect a B2B marketing org that is truly accountable for pipeline and revenue, not just “influence”Aligning product, content, and campaign teams to ONE goal: pipeline creation (culture, incentives, and operations)The “Value Chain” framework for mapping marketing’s full-stack impact across the GTM engineJohn’s “4 Whats” Framework for operationalizing measurement: what's working, what's not, what's new, what's nextWhat’s broken about attribution today and why multi-touch measurement is often a red herringThe shift from SEO to GEO: How generative AI is re-writing digital discoverability and B2B content strategyAI in marketing without losing authenticity: human-in-the-loop, voice, and trust factors you need to watchWhy more Martech isn’t the answer (and the tech stack crisis facing GTM teams)Deep problem understanding as a GTM superpower (what chess can teach SaaS leaders about winning)Key moves for founders and GTM leaders facing today’s attention and signal problemGuest Speaker Links (John Fernandez):LinkedIn: https://www.linkedin.com/in/johnfernandez/Datasite: https://www.datasite.com/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://substack.com/@sophiebuonassisiWhere to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/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.
--------
1:04:00
--------
1:04:00
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-to-door restaurant sales and now builds GTM from the ground up, helping 50% of the population with dietary needs find safe, personalized dining experiences.Discussed in this Episode:Transitioning from CRO to founder (and why it’s so humbling)Tactical frameworks for finding product-market fit (especially in early pivots)Building a GTM motion from zero using community and customer obsessionWhat AI actually changes in GTM (hint: it’s not just about productivity)How to treat fundraising like a sales motion (including identifying your ICP)Practical tools Erica is using to build GTM motions faster with fewer resourcesHighlights:00:45 From Sales to CRO: The Unconventional Path02:47 Why Being a Generalist Can Make You a Better Leader05:31 What AI Is Really Doing to GTM Roles06:33 Scaling Yourself Before You Scale Your Team08:00 From CRO to Founder: Sales Skills That Transfer to Fundraising10:10 Fundraising Is Just Another Sales Funnel14:12 Relationships Compound in GTM and Fundraising22:33 Finding PMF by Listening Hard26:04 When Your GTM Motion Becomes Compliance-Driven27:41 Community as a GTM Lever (Not Just a Buzzword)38:28 Pre-PMF vs. Post-PMF42:53 Turning Messy Data into Valuable Content56:12 Tools Over Headcount: Erica’s Favorite AI StackGuest Speaker Links (Erica Anderman):LinkedIn: https://www.linkedin.com/in/ericaandermanFoodini: https://foodini.co/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/insophiebuonassisiNewsletter: https://substack.com/@sophiebuonassisiThanks to Our Sponsor – UserEvidence:UserEvidence is the Customer Evidence Platform that helps you collect feedback, surface proof points, and turn customer wins into bite-sized assets your sales and marketing teams can actually use. Capture social proof at scale. Arm reps with credible stories. Close more deals with trust.Learn more at: https://userevidence.com/gtmnowWhere to Find GTMnow:Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/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.
--------
1:00:04
--------
1:00:04
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 discover businesses, why your structured data now matters more than your homepage, and what you can do to stay ahead.This is a clip from the full episode with Mike — a must-watch roadmap for the AI-driven future of marketing. Hit the links to dive into the full conversation.• GTMnow: https://gtmnow.com/gtm-146-future-of-search-ai-digital-presence-mike-walrath/• Apple: https://podcasts.apple.com/in/podcast/gtm-146-the-future-of-search-ai-and-digital/id1369291464• Spotify: https://open.spotify.com/episode/2xs4xXGmTTKXHSNUMmYqvy• YouTube: https://www.youtube.com/watch?v=4m1051j_hq4&t=1332sThanks to our Sponsor: QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.Visit us: https://gtmnow.com/Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow/Follow us on Twitter/X: https://x.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.
--------
21:06
--------
21:06
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 simplificationBuilding and scaling B2B SaaS companiesRevenue operations (RevOps) and AI integrationSerial entrepreneurship and company buildingTransitioning from big tech to startup founderHighlights: 04:35 From Fliptop to LinkedIn: how Doug navigated acquisition and scaled Sales Navigator.06:33 Why Sales Nav was a $250M business with a “crappy product” — and how Doug turned it around.09:56 Doug’s “awesome test” for hiring top talent (and the 90-day rule he swears by).13:26 The speed dating hack that landed Coffee’s first sales leader.17:36 What Doug learned running Sales Cloud at Salesforce — and why he left.22:22 The biggest missed opportunity inside Sales Navigator (and what he’d do differently).24:37 Why sales tech stacks are bloated — and how AI-native CRMs solve it.28:36 What makes a true AI-native product (and why Coffee is built different).31:36 The Rippling-inspired vision behind Coffee’s GTM strategy.34:47 Three versions of Coffee — and why reps are swiping their own cards.39:44 AI agents vs. simple automations — what the future actually looks like.42:41 Why SDRs won’t disappear — but their job will change.47:45 Data as the new moat: how to build durable product advantage in the AI era.50:08 Why Doug runs a podcast and thinks every startup should act like a media company.55:09 The new math of headcount: scaling to $100M+ with fewer hires.56:45 The “TAM is dead” take — and how Doug thinks about modern segmentation. Guest Speaker Links (Doug Camplejohn):LinkedIn: https://linkedin.com/in/camplejohnCoffee: https://coffee.aiPodcast: https://www.coffee.ai/podcastHost Speaker Links (Sophie Buonassisi):LinkedIn: https://linkedin.com/in/sophiebuonassisiNewsletter: https://substack.com/@sophiebuonassisiThanks to our Sponsor: TriNetEvery early-stage founder is told to focus on product and growth. But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey.“Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth. Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical. TriNet exists to make that easier. TriNet’s full suite of HR solutions is designed to support companies at critical inflection points – from early traction to scale. Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_ YouTube: https://www.youtube.com/@GTM_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/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.
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.
Ireland