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 revenue organizations with intention.Discussed in this EpisodeWhy GTM roadmaps should be “forward-compatible”Iteration cycles in GTM vs. product roadmapsEarly lessons from Plaid’s rudimentary qualification processRecognizing high-value clients vs. anti-patterns in inbound leadsHow daily standups created fast GTM learning loopsShifting from PLG to sales-led motions with SDRs and routingSequencing GTM expansion: fintech → enterprise FSIs → embedded fintechCompensation design mistakes and their impact on sales behaviorEpisode Highlights00:00 — Why GTM roadmaps should be built “forward-compatible”01:53 — How Plaid iterated through 9–10 GTM versions in the first year05:12 — Plaid’s early qualification process: 4 simple questions07:28 — Why most inbound leads weren’t equal—and how Plaid spotted patterns10:01 — Using daily standups twice a day to refine GTM qualification14:32 — How Plaid’s GTM roadmap evolved from monthly to yearly cycles20:46 — Moving beyond partnerships to diversify top-of-funnel channels24:53 — Scaling into enterprise financial institutions with tailored product needs27:09 — Entering phase three: embedded fintech with customers like Tesla30:00 — Compensation design mistakes that slowed deals and created riskThis episode is brought to you by: HarmonicHarmonic helps you discover the best startups way ahead of the competition. We use it at GTMfund, as do thousands of investors at firms like USV and Insight. GTM teams at companies like Notion and Brex also rely on the platform to stay ahead.Harmonic tracks millions of startups and lets you search using simple filters or natural language to match exactly what you’re looking for. When you find a company that looks interesting, Harmonic pulls everything into one place (founder backgrounds, traction, and market data) so you can quickly evaluate and understand if it’s a fit.At GTMfund, we even have a private Slack channel called #companywatchlist powered entirely by Harmonic.Guest LinksLinkedIn:https://www.linkedin.com/in/paulrwilliamsonHost LinksLinkedIn:https://www.linkedin.com/in/sophiebuonassisiX (Twitter):https://x.com/sophiebuonaNewsletter:https://thegtmnewsletter.substack.comThe 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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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 differentiated narratives that drive credibility, legitimacy, and growth.Discussed in This EpisodeWhat PR actually is (and isn’t) for startupsThe difference between positioning, storytelling, and PR — and how they stack togetherWhen PR makes sense and when to hold back on announcementsStep-by-step process for landing coverage in top outlets like TechCrunch or ForbesHow to build authentic relationships with reporters before you pitchWhat makes something truly newsworthy: timeliness, impact, relevanceTactical advice for pitching, interviews, and amplifying coverage post-launchHow PR fits into the broader go-to-market motionEpisode Highlights00:00 — Positioning, storytelling, and PR defined02:23 — Jenny explains what PR really is and why startups misunderstand it06:39 — The first step before any PR push: setting clear goals11:37 — Example of a newsworthy founder story: building an AI radiologist from personal experience15:17 — The three elements of newsworthiness: timeliness, impact, and relevance17:42 — Why building warm relationships with reporters is crucial20:36 — Preparing for the interview itself vs. outreach22:47 — Amplifying coverage through your network post-publication25:07 — What PR agencies cost (and why no one can guarantee coverage)29:18 — Jenny’s #1 book recommendation on positioningThanks to Our Sponsor – Clarify:Clarify is the autonomous CRM built for founders and early-stage teams who want to build more pipeline, close more deals, and spend way less time on busywork.Clarify automatically enriches your contacts, captures leads from anywhere (even one click from LinkedIn), and keeps your pipeline up to date on its own, so you can focus on winning deals, not updating fields.If you’re looking to simplify your stack and help your team move faster, check out Clarify.Recommended BooksPositioning: The Battle for Your Mind by Al Ries & Jack Trout — Jenny’s #1 recommendation for founders learning positioning fundamentals.ReferencedClarify (autonomous CRM): https://clarify.aiTechCrunch: https://techcrunch.comForbes: https://forbes.com New Lantern (portfolio company example): https://newlantern.aiSquare: https://squareup.comGuest LinksLinkedIn: https://www.linkedin.com/in/jennyheX (Twitter): https://x.com/jennydhe Website: https://positionventures.comThe 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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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 launched Copilot, its flagship AI product, and executed a bold shift upmarket — transitioning from transactional selling to a data-first, enterprise-driven GTM strategy.Discussed in This EpisodeHow ZoomInfo transitioned from transactional selling to enterprise go-to-marketThe "Good Co, Bad Co" framework for segment-specific product retentionWhy ZoomInfo changed its ticker symbol to GTMLaunching Copilot and driving $100M revenue in under 6 monthsHow internal AI usage became the go-to-market motionKey shifts in comp design and team segmentation for scaling upmarketUsing telemetry and real-time signal tracking to measure rep effectivenessLessons in long-term execution vs. short-term growth pressureEpisode Highlights00:00 — ZoomInfo's evolution from a sales tool to a data-first platform17:06 — Why data as a service is ZoomInfo’s fastest-growing business20:43 — How to build and apply the “Good Co, Bad Co” segmentation framework26:26 — The hard part about going upmarket? Aligning the full funnel org30:19 — Changing your ticker to GTM: A bold positioning play34:31 — Copilot’s $100M launch: The power of internal usage39:53 — Most AI tools show <5% revenue lift. Here's why43:29 — How ZoomInfo is operationalizing AI across the org48:29 — The signals > activity shift in modern sales measurement52:18 — What James wants future CROs to steal: Think long-term, build patientlyThanks 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/gtmnowGuest Links LinkedIn: https://www.linkedin.com/in/james-roth-3a913b51/Host Links LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.com/Website: https://gtmnow.comWhere to Find GTMnow• Website: https://gtmnow.com• LinkedIn: https://www.linkedin.com/company/gtmnow/• X (Twitter): https://x.com/GTMnow_• YouTube: https://www.youtube.com/@GTM_now• The GTM Podcast: 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.
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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, Stevie previously held senior roles at Twilio, where she helped grow the enterprise business to a $1B run rate. Discussed in This EpisodeHow Stevie’s path from pro gamer to CRO shaped her competitive edgeEarly-stage chaos at Vanta and the signs of undeniable product-market fitBattling over 40 copycat competitors with value selling and a “CIA” competitive squadWhy execution, not first-mover advantage, is the only sustainable moatThe challenges and lessons from scaling SMB sales and moving into enterpriseBuilding go-to-market experiments before committing product investmentTransforming post-sales into a growth engine and driving net retention upStevie’s view on AI in revenue operations and personal productivityEpisode Highlights00:00 — “Every business is subject to the laws of physics and math… Execution is the only moat.”03:07 — Stevie on becoming the world’s first female pro gamer and how competitiveness fueled her career.06:25 — The undeniable product-market fit that convinced Stevie to join Vanta.14:02 — Facing 40+ copycat competitors and learning that flashy marketing can’t beat sustainable growth.16:23 — Transitioning from transactional selling to deep, value-based discovery using MEDDPICC.18:30 — Creating Vanta’s “CIA” Competitive Intelligence Agency to win back customers.26:10 — Launching the experimental enterprise sales team and the patience it took to scale it.47:08 — Rebuilding post-sales into separate customer success and account management functions.50:56 — Vanta’s next big GTM bets: platform sales, public sector, and deeper enterprise expansion.53:27 — How Stevie is using AI in revenue operations and her own work life.Guest LinksLinkedIn: https://www.linkedin.com/in/steviecaseThanks 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.
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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.
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.
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