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 decades studying what actually separates companies that scale from those that stall.

In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator.

In this episode, we discuss:

- Why understanding customer pain matters more than having a great idea

- Why early selling should optimize for learning, not revenue

- Why founders can’t outsource sales too early

- How distribution becomes a competitive advantage at scale

- What makes “unlikely entrepreneurs” outperform expectations

- Why small, high-quality teams beat large organizations

- Why churn is a symptom, not the root problem

- How product-market fit quietly changes as companies grow

- Why founders must evolve from heroic sellers to system builders

- How culture becomes a real go-to-market asset

Lou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer.

If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most.

Timestamps:

00:00 – What actually makes a company great

00:26 – Why early selling is about learning, not revenue

01:47 – Why founders misunderstand customer pain

02:06 – “If you build it, they will come” is a lie

02:33 – Distribution as the real moat

02:58 – What makes an “unlikely entrepreneur” succeed

06:15 – Why age and experience increase founder success

07:01 – Curiosity, coachability, and risk elimination

09:29 – Why founders can’t outsource sales too early

15:26 – Pattern recognition vs short-term ARR

21:10 – Founder-led sales vs scalable systems

29:12 – Leadership, culture, and delegation

33:18 – Founder evolution from $1M to $100M

38:24 – When product-market fit starts to break

39:15 – Why churn is a lagging indicator

39:54 – Why small teams outperform large ones

44:22 – Lessons from Unlikely Entrepreneurs

45:23 – Final advice for founders

Sponsors:

HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com

Guest links:LinkedIn: https://www.linkedin.com/in/loushipley/X: https://twitter.com/loushipleyHost (Sophie Buonassisi) links:LinkedIn:  https://www.linkedin.com/in/sophiebuonassisi/X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comHost (GTMnow) links: https://gtmnow.com

Follow us on LinkedIn:

https://www.linkedin.com/company/gtmnow/

Follow us on X (Twitter):

https://x.com/GTMnow_

Follow us on YouTube:

https://www.youtube.com/channel/UCGQM23b5lZbcfLtHAe87J_A

Follow us on TikTok:

https://www.tiktok.com/@gtmnow_

Follow us on Instagram:

https://www.instagram.com/gtmnow_/

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, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition.

In this episode, we discuss:

- Why in-person events are becoming a premium GTM channel in an AI-first world

- How founders can de-risk distribution before building the product

- The most common internal missteps that derail startups early

- Why offsites are the new HQ for remote and hybrid teams

- How to design offsites that drive alignment, not just fun

- What makes a dinner actually work — including overlooked details like acoustics

- How teams use events for customer acquisition and partnerships

- Why kindness and positivity can be a real leadership advantage

Healey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.

If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world.

Timestamps:

00:00 – Why founders underestimate distribution

03:30 – Product vs distribution: what actually matters early

06:45 – Why most startups fail from internal misalignment

10:30 – Culture, communication, and focus as scaling constraints

14:40 – Hybrid work broke alignment

17:45 – Why offsites are becoming the new HQ

21:30 – Events as a go-to-market strategy

25:00 – AI, outbound fatigue, and inbox trust collapse

28:40 – “In-person experiences are becoming a premium”

32:30 – How to use events for customer and partner acquisition

36:15 – What makes a high-impact event vs a wasted one

39:50 – Dinners, summits, and unforgettable experiences

43:30 – Leadership, kindness, and “don’t be a jerk”

47:40 – Mental state as a competitive advantage

52:30 – Final reflections and advice for founders

Sponsors:

HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com

Guest links:Instagram: https://www.instagram.com/healeycypher/?hl=enHealey’s podcast: https://www.dontbeajerkpodcast.com/

Mentioned Resources:

Host (Sophie Buonassisi) links:

X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comHost (GTMnow) links: https://gtmnow.com

Follow us on LinkedIn:

https://www.linkedin.com/company/gtmnow/

Follow us on X (Twitter):

https://x.com/GTMnow_

Follow us on YouTube:

https://www.youtube.com/channel/UCGQM23b5lZbcfLtHAe87J_A

Follow us on TikTok:

https://www.tiktok.com/@gtmnow_

Follow us on Instagram:

https://www.instagram.com/gtmnow_/

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 in startups and scaling companies.

This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.

If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.

In this episode, we cover:

• Why most GTM motions fail at scale, even with strong products
• What it really means to treat go-to-market like a product
• How AI changes execution without changing fundamentals
• The rise of the forward deployed engineer
• Why “lost on price” is usually a lie
• What great sales reps still do better than anyone in the AI era
• How to think about joining companies “early” without getting timing wrong

Listen if GTM feels fragile, unpredictable, or overly dependent on heroes.

Timestamps

00:00 – Introduction

01:00 – “Yes is great. No is great. Maybe will kill you.”

02:00 – Why go-to-market should be treated like a product

04:45 – Designing the experience of being sold to

06:30 – Using AI to debug GTM process failures

09:00 – Why “lost on price” usually isn’t about price

12:00 – What go-to-market engineering actually is

16:00 – The rise of the forward deployed engineer

20:45 – AI, agents, and what still needs human judgment

25:45 – What great sales reps do differently in the AI era

29:30 – Why GTM roles are becoming more consultative

33:30 – Will there be an AI reckoning?

38:00 – What “joining early” really means

42:00 – Career lessons from Google, Stripe, and Vercel

44:00 – Closing thoughts

Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping the company navigate hypergrowth. 

Discussed in this episode

• Why Mark studied international relations, and why venture feels like “the liberal arts of jobs”
• Index’s US “invisibility” era and what that taught him about building a new firm
• The Chemistry spinout thesis: “take great multi-stage DNA, reconstitute it with focus”
• Fund design: pre-seed → seed → A, light reserves, and concentrated doubling-down
• Hiring strategy: network access > spreadsheet diligence
• Culture principles: excellence, performance, “no one takes themselves too seriously”
• Conviction-based investing vs consensus IC, and why omissions are the real killer
• The hardest lesson in venture: managing co-founder dynamics (and when to just listen)

Episode highlights

00:00 — “A+ people want to work with A+ people.”

01:46 — GTMfund’s 2026 prediction: big players come roaring back (Google, Meta, Microsoft, Uber/Waymo).

14:51 — GTMfund platform metrics: thousands of support items, intros, hires, and fundraising connects.

26:29 — Why Mark left Index to build Chemistry: big-fund lessons, rebuilt with focus.

33:39 — Chemistry’s strategy: early-stage focus, light reserves, and building for “product-market discovery.”

44:05 — “Venture doesn’t scale well.” Why Chemistry stays small to avoid bureaucracy.

49:59 — Events that actually work: chess tournaments, surfing, and hobby-driven gathering > happy hours.

54:56 — Investment process: conviction, not consensus—optimize for outliers, not averages.

1:10:32 — Hardest lesson in venture: co-founder dynamics, and learning when to listen (not “advise”).

Brought to you by: AngelList

From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.

As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture. 

They’ve scaled with us across funds and into the future.

If your fund is growing in size or complexity, check them out at www.angellist.com/gtmfund.

Follow Mark Goldberg

• LinkedIn: https://www.linkedin.com/in/mark-goldberg-25458110
• X (Twitter): https://x.com/Mark_Goldberg_X (formerly Twitter)
• Chemistry (website): https://www.chemistry.vc/Chemistry

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.

Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100.

Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Objects, and IBM. He is also a General Partner at GTM Operators Network, investing from seed through growth, and is deeply committed to mentorship and advancing underrepresented leaders in tech.

Discussed in this episode:

• Why “AI-led growth” can hide churn and value erosion
• Lagging vs leading indicators for retention endurance
• Why the CS investment benchmark is shifting from 10% → ~7%
• A simple “waterfall” for allocating post-sales budget: support → onboarding → outcomes
• How to “lever up” the envelope with premium support + professional services
• Why expansion (not renewals) is the early signal of product-market fit
• The rise of AI-powered specialized generalists in post-sales
• When forward deployed engineers make sense (and when they’re just a fad)

Episode highlights

00:00 — Why customer expansion is the real signal of product-market fit

00:50 — Lagging revenue vs. leading indicators of endurance

04:11 — Why the CS benchmark dropped from 10% to 7%

08:41 — How AI moved from internal efficiency to customer-facing leverage

11:41 — Why retention cost matters more than CAC in the AI era

14:17 — The simplest framework for allocating the 7% CS budget

18:53 — Founder-led CS, design partners, and early-stage PMF myths

23:16 — The rise of AI-powered specialized generalists

30:00 — When forward-deployed engineers actually make sense

49:31 — The one rule for building a durable SaaS company

This episode is brought to you by our sponsor: HockeyStack

If you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next.

HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale what works. That’s why teams like RingCentral, Outreach, ActiveCampaign, and Fortune 100 companies rely on HockeyStack to eliminate wasted spend, take better decisions, and make space to think.

Learn more at hockeystack.com

Follow Abbas Haider Ali

• LinkedIn: https://www.linkedin.com/in/abbashaiderali
• X (Twitter): https://x.com/abbashaiderali
• GitHub: https://github.com/AbbasHaiderAli

Follow Sophie Buonassisi (Host)

• LinkedIn: https://www.linkedin.com/in/sophiebuonassisi
• X (Twitter): https://x.com/sophiebuona
• Newsletter: https://thegtmnewsletter.substack.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.

Adam Carr is the Chief Revenue Officer at Apollo, where he’s scaling revenue by layering sales on top of a $150M+ ARR product-led growth engine. Previously, Adam helped scale Miro from a PLG-led company into a global sales organization, contributing to its growth into a $17.5B business. He’s known for building systems-driven GTM teams that turn product signals into durable revenue.

Discussed in this episode

• Why PLG is gravity (signals + acquisition) and sales is the monetization layer
• The “one-team” model to prevent PLG vs. sales cannibalization
• Building talent density (and why slowing hiring can be the fastest path)
• Hiring for curiosity, coachability, ownership, and team-first execution
• The “architect / systems thinker” profile for modern sellers
• A new post-sales model: CSMs → technical GTM Engineers + intervention-led journey
• Using customer journey milestones to drive expansion and prevent churn proactively
• AI in GTM: streamlining manual work so humans focus on better conversations

Episode highlights

00:00 — PLG is about signaling + acquisition (not monetization)

01:30 — “PLG isn’t the monetization way… it’s layering sales.”

02:41 — Talent density: hire for the next 12–18 months, not just “today”

04:50 — The soft skills that scaled Miro: curiosity, coachability, ownership

08:38 — Why Adam hires “architects” (system thinkers) instead of just sellers

10:41 — The mindset shift: celebrate value realized, not contracts signed

15:41 — Replacing CSMs with “go-to-market engineers” + an intervention model

19:14 — Turning PLG signals into PQA/PQL routing (and reducing the “noise”)

29:26 — “100M ARR is late” — when to start layering sales into PLG

Guest links

• LinkedIn (Adam Carr):https://www.linkedin.com/in/adamhcarr

Follow Sophie Buonassisi (Host)

• LinkedIn: https://www.linkedin.com/in/sophiebuonassisi
• X (Twitter): https://x.com/sophiebuona
• Newsletter: https://thegtmnewsletter.substack.com

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
• Podcast Directory: 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.

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.

Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board.

Discussed in this episode:

• How Cassie “accidentally” became a VC after 15 years in GTM leadership.
• The career advice Bill Gurley gave her that changed her trajectory.
• Why Primary refuses to say “platform” and instead built a 30-person Impact team.
• How she actually sources pre-seed/seed founders before they leave their jobs.
• Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).
• The difference between real traction vs. “happy ears” and fake design partners.
• Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.
• How operators can actually break into VC (hint: it’s all about doing the work).

Episode highlights

00:35 — Clay, usage-based pricing, and the $100M ARR rocketship

09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t)

14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb

22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path

27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders

36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”)

46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor

57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features

1:01:29 — So you want to be a VC: Cassie’s playbook for operators to break into venture (without delusion)

Brought to you by: AngelList

How did we build the GTMfund back office? Easy!

We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.

For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.

If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.

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.

Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.

Discussed in this episode

• Why classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.
• How the Bowtie model exposes the real levers of growth that funnels hide.
• Why PLG-style thinking is now essential even for sales-led and enterprise motions.
• The 3 first principles of freemium: empathy, generosity, and metrics.
• Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.
• How to design hybrid human + AI workflows using a clear data model, not vibes.
• What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).
• Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.

Episode highlights

00:00 — GTM is still running 20-year-old playbooks

01:29 — “Sales, marketing, CS… the last unengineered engine”

03:20 — The myth of “just add more heads”

05:50 — The Fundly story: reinvention, too late

08:30 — Why Freemium had to be written

11:01 — Three first principles of freemium

15:25 — Mapping AI across the entire customer journey

19:29 — “Automate the predictable, humanize the exceptional”

25:18 — What the Bowtie exposes that funnels hide

27:25 — Building a “minimum viable Bowtie

This episode is brought to you by our sponsor: ZoomInfo

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Dave Boyce (Guest)

• LinkedIn: https://www.linkedin.com/in/boycedave
• Substack: https://daveboyce.substack.com

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
• Podcast Directory: 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.

Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.

Discussed in this episode

• The evolution of partner selling — from VARs to SIs to ecosystems
• How to know if partner selling fits your GTM model
• The delivery-first mindset that drives retention
• Direct vs. partner motion: Microsoft vs. Salesforce
• Why enablement is the #1 green flag for partner success
• Partner marketing: how to make resellers self-sustaining
• Using AI to power future-ready GTM models
• The case for hybrid work in high-performance sales cultures

Episode Highlights

00:00 — The “year four” moment when partners are selling for you

01:07 — 30 years of selling through partners in New York

03:22 — Start partner strategy with delivery, not distribution

06:32 — Why partner selling creates “superhuman” sellers

09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid

12:13 — The startup hack: sell delivery on your paper, subcontract partners

17:16 — A 90-day playbook for integration partnerships

21:39 — Hiring the right people to build a partner business

27:18 — How Sisense runs delivery partners and an Australian reseller

29:55 — White-labeling Snowflake: using resell to get the giant’s attention

This episode is brought to you by our sponsor: BoomPop

We’re deep in event planning right now, as no doubt many of you are.

Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.

Follow Brian Weinberger

• LinkedIn:https://www.linkedin.com/in/brianweinberger

Recommended Books

• What Great Salespeople Do by Michael Bosworth & Ben Zoldan — The power of storytelling in sales
• The Power of Nice by Linda Kaplan Thaler & Robin Koval — Why kindness compounds in business
• Sacred Hoops by Phil Jackson — Coaching and leadership lessons from the Bulls dynasty

Referenced

• Sisense: https://www.sisense.com
• Snowflake: https://www.snowflake.com
• AWS: https://aws.amazon.com
• Salesforce: https://www.salesforce.com
• Microsoft: https://www.microsoft.com
• Accenture (SI example): https://www.accenture.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.

This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.

Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.

This is a clip from the full episode with Cristina (an inside look at the judgment frameworks behind Stripe, Notion, and now Linear) and the practical filters every GTM leader can use to pick winners early.

Discussed in This Clip

• How to recognize “exceptional” even outside your own domain
• Finding early proof a product is truly beloved (signals > vanity metrics)
• Starting with a sharp market wedge, then earning the right to expand
• Why founders who excel at something—anything—tend to excel at company-building
• What to expect from early operators: founder mode and bias to execute
• Sales hiring for technical buyers (and why quotas can help earlier than you think)
• Aligning tightly with founders as an exec: relationships drive outcomes
• How to assess GTM on day one: ride-alongs, raw customer feedback, ground truth

Highlights

00:00 — The difference between good and great—and how to spot it across functions

00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early

01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane

03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)

04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)

07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)

12:52 — What great early leaders do: see problems, create strategy, then execute

16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner

21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observation

This episode is brought to you by our sponsor: BoomPop

We’re deep in event planning right now, as no doubt many of you are.

Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.

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.