The GTMnow Podcast

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.