The GTMnow Podcast

Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved.

Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based pricing model backed by up to a $1M performance guarantee if resolution targets aren’t met.

In this episode, we cover:- Why customer support is fundamentally a 24/7 business

- How Fin now handles 80%+ of customer queries through automation
- Why human empathy often breaks down in real-world support workflows
- How AI makes instant, individualized service possible for the first time
- Why Intercom put a million-dollar guarantee behind its resolution rate
- What it takes to confidently price software on outcomes
- Why the future of support is humans + AI

Guest links:

- Archana Agrawal - LinkedIn: https://www.linkedin.com/in/archana-agrawal/

- Intercom - LinkedIn: https://www.linkedin.com/company/intercom/

- Intercom’s Fin Agent: https://fin.ai/

Host links:
- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona
- Newsletter: https://thegtmnewsletter.substack.com

Sponsors:

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

Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to granola.ai/gtmfund  and get three months free with the code GTMFUND.

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com/

Highlights:
00:00 – Why Intercom went all-in on AI
03:23 – What Fin is and how it changes customer support
05:27 – How Fin scaled to a 67% resolution-rate
06:38 – The thinking behind 99¢ outcome-based pricing
08:54 – Why customers don’t want to pay for activity
09:10 – How outcome-based pricing aligns incentives
09:57 – What changed for sales, success, and revenue operations
15:10 – How Intercom thinks about forward-deployed engineers
16:22 – Why the future is humans + AI
18:56 – The real moat: product feedback loops at scale
19:32 – Why Intercom put a million-dollar guarantee behind results
23:29 – Why enablement is now the GTM bottleneck
32:24 – From $1M to nearly $100M: what Fin’s growth reveals
38:26 – Hiring in a world with no playbooks
42:20 – How Archana learns from podcasts, books, and customers

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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.