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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 Episode
Episode Highlights
00:00 — Why GTM roadmaps should be built “forward-compatible”
01:53 — How Plaid iterated through 9–10 GTM versions in the first year
05:12 — Plaid’s early qualification process: 4 simple questions
07:28 — Why most inbound leads weren’t equal—and how Plaid spotted patterns
10:01 — Using daily standups twice a day to refine GTM qualification
14:32 — How Plaid’s GTM roadmap evolved from monthly to yearly cycles
20:46 — Moving beyond partnerships to diversify top-of-funnel channels
24:53 — Scaling into enterprise financial institutions with tailored product needs
27:09 — Entering phase three: embedded fintech with customers like Tesla
30:00 — Compensation design mistakes that slowed deals and created risk
This episode is brought to you by: Harmonic
Harmonic 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 Links
Host Links
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.
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 Episode
Episode Highlights
00:00 — Positioning, storytelling, and PR defined
02:23 — Jenny explains what PR really is and why startups misunderstand it
06:39 — The first step before any PR push: setting clear goals
11:37 — Example of a newsworthy founder story: building an AI radiologist from personal experience
15:17 — The three elements of newsworthiness: timeliness, impact, and relevance
17:42 — Why building warm relationships with reporters is crucial
20:36 — Preparing for the interview itself vs. outreach
22:47 — Amplifying coverage through your network post-publication
25:07 — What PR agencies cost (and why no one can guarantee coverage)
29:18 — Jenny’s #1 book recommendation on positioning
Thanks 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 Books
Referenced
Guest Links
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.
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 Episode
Episode Highlights
00:00 — ZoomInfo's evolution from a sales tool to a data-first platform
17:06 — Why data as a service is ZoomInfo’s fastest-growing business
20:43 — How to build and apply the “Good Co, Bad Co” segmentation framework
26:26 — The hard part about going upmarket? Aligning the full funnel org
30:19 — Changing your ticker to GTM: A bold positioning play
34:31 — Copilot’s $100M launch: The power of internal usage
39:53 — Most AI tools show <5% revenue lift. Here's why
43:29 — How ZoomInfo is operationalizing AI across the org
48:29 — The signals > activity shift in modern sales measurement
52:18 — What James wants future CROs to steal: Think long-term, build patiently
Thanks 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/gtmnow
Guest Links
Host Links
Where 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.
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 Episode
Episode Highlights
00:00 — “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 Links
LinkedIn: https://www.linkedin.com/in/steviecase
Thanks to our Sponsor: Qualified
Piper 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.
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 episode
Episode Highlights
00:00 — Everyone is doing all the work—but you're winning by chance, not by design
02:01 — Gaurav on seeing growth as a systems function, not just marketing
13:33 — Culture alone delivered roughly half of the 3× CAC reduction at ClickUp
15:53 — Gaurav defines incrementality testing vs. flawed attribution models
29:27 — Setting input KPIs so squads deliver a “win every week” keeps momentum high
32:53 — AI is being embedded across PLG + GTM workflows—from content briefs to deal signals
Recommended Books
Referenced
Guest Links (Gaurav Agarwal):
Host Speaker Links (Sophie Buonassisi):
Where to find GTMnow (GTMfund’s media brand):
Thanks to our Sponsor: Qualified
Piper 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.
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:
Guest Speaker Links (John Fernandez):
Host Speaker Links (Sophie Buonassisi):
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_now
The 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.
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:
Highlights:
00:45 From Sales to CRO: The Unconventional Path
02:47 Why Being a Generalist Can Make You a Better Leader
05:31 What AI Is Really Doing to GTM Roles
06:33 Scaling Yourself Before You Scale Your Team
08:00 From CRO to Founder: Sales Skills That Transfer to Fundraising
10:10 Fundraising Is Just Another Sales Funnel
14:12 Relationships Compound in GTM and Fundraising
22:33 Finding PMF by Listening Hard
26:04 When Your GTM Motion Becomes Compliance-Driven
27:41 Community as a GTM Lever (Not Just a Buzzword)
38:28 Pre-PMF vs. Post-PMF
42:53 Turning Messy Data into Valuable Content
56:12 Tools Over Headcount: Erica’s Favorite AI Stack
Guest Speaker Links (Erica Anderman):
LinkedIn: https://www.linkedin.com/in/ericaanderman
Foodini: https://foodini.co/
Host Speaker Links (Sophie Buonassisi):
LinkedIn: https://www.linkedin.com/insophiebuonassisi
Newsletter: https://substack.com/@sophiebuonassisi
Thanks 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/gtmnow
Where to Find GTMnow:
Website: https://gtmnow.com/
LinkedIn: https://www.linkedin.com/company/gtmnow/
Twitter/X: https://x.com/GTMnow_
YouTube: /@gtm_now
The 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.
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=1332s
Thanks to our Sponsor: Qualified
Piper 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.
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:
Highlights:
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):
Host Speaker Links (Sophie Buonassisi):
Thanks to our Sponsor: TriNet
Every 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_now
The 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.
Austin Hughes is the founder and CEO of Unify, a platform helping high-growth teams turn buying signals into pipeline. Previously, Austin led the growth team at Ramp, where he scaled the org from 1 to 25+ and pioneered a product-led, experiment-driven GTM approach. With a background in investment banking and venture capital, Austin brings a uniquely analytical and first-principles mindset to modern B2B growth.
Discussed in this Episode:
Highlights:
04:00 Ramp’s growth org: running 100+ experiments per quarter
08:45 Why LinkedIn became Unify’s silver bullet
11:30 Austin’s content creation workflow (and why he doesn’t use AI to write)
13:00 Technical vs. traditional growth marketers—how to hire for impact
17:00 Using Unify to merge 1st & 3rd-party data into a signal pipeline
20:30 How automation + human-in-loop GTM creates leverage
24:00 Austin’s Carta example: what perfect relevance looks like
27:00 What broke in outbound and why signal-based selling is the fix
32:00 When startups should start ingesting signals
36:30 Culture of experimentation: “failure is just a data point”
39:00 How Unify is using AI internally for GTM and support ops
43:00 What’s coming next: AI-relevant messaging, BDR collaboration tools
47:00 The end of traditional marketing roles—and what comes next
Guest Speaker Links (Austin Hughes):
Host Speaker Links (Sophie Buonassisi):
Where to find GTMnow (GTMfund’s media brand):
Thanks to our Sponsors:
TriNet
Founding a company is hard enough. Navigating payroll, benefits, and compliance shouldn’t slow you down. That’s where TriNet comes in. They work with startups and scaling businesses to help take HR off your plate, so you can stay focused on building product, growing revenue, and hiring great people - the go-to-market engine. B2B companies like Hivebrite and Equilend trust TriNet to help handle the infrastructure of their workforce, so their teams can focus on execution. Sponsor Link: https://trinet.com/gtmnow
Unify
Timely enough, Unify is also launching something big today — Unify for Sales Reps, their new AI-native system-of-action built to help sales teams work smarter and move faster. With powerful features like an AI
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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