The GTMnow Podcast

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG).
But the path there was anything but smooth.

In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.

We cover:
- Why Figma refused to discount, even when Microsoft pushed back
- How to hire the right first sales rep as a founder
- The PLG to enterprise transition most companies get wrong
- What the Adobe deal collapse actually felt like from the inside
- How Figma went from 3 products to 8 overnight and launched into an IPO
- What great sales look like in the AI era

Timestamp:
0:00 – Intro
1:02 – Guest intro: Kyle Parrish
1:35 – Joining Figma at $2M ARR in 2018
5:01 – First meeting with Dylan (Figma CEO)
6:13 – How to find your first sales hire
9:05 – Stage alignment in early hiring
11:43 – Early-stage operators need "scar tissue"
13:19 – Northstar metric at Figma
14:13 – Obsessing over customer conversations
16:44 – Building Figma's brand through community
17:31 – Scaling the "unscalable"
20:08 – In-person GTM vs. digital
22:47 – Was there a moment Figma might not make it?
24:48 – Pivoting after the Adobe deal collapsed
28:10 – Figma's no-discount rule
31:05 – Enterprise ELAs replacing discounting
34:47 – What makes a great salesperson in the AI era
36:56 – Missionaries vs. mercenaries in AI-era GTM
39:47 – Spotting the next Dropbox or Figma
43:46 – Kyle's post-Figma investing focus
45:58 – Family, travel & what's next

Guest: Kyle Parrish, former VP Sales at Figma
LinkedIn: https://www.linkedin.com/in/kparrish8/
X: https://x.com/KyleHParrish

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

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

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AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.
Sam, Founder and CEO of Test Box, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.
If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.
What we cover:
Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)
The shift from discovery calls to validation calls, and how to prepare
CEO (AI-version of SEO): how LLMs are shaping what buyers believe about your product
The "day one shortlist" shrinking from 3-4 vendors to 1-2 vendors
Agent-to-agent procurement: Sam's timeline for when AI agents fully take over buying
Why the mid-funnel is actually getting longer, not shorter
The "Fake Nothing, Prove Everything" campaign that went viral post-Series A
How Test Box runs 15 AI experiments per week across the entire company
Using Google Vertex video analysis to read prospect body language on sales calls
How to build an AI-first culture without burning out your team
Books: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to Great

Timestamps:0:00 - Cold open
1:09 - What Test Box does
2:43 - How buying has changed
5:48 - What founders/CROs should do now
7:05 - GEO: AI version of SEO
9:02 - Why mid-funnel is expanding
21:17 - Agent-to-agent procurement
26:02 - All procurement by agents in 3-5 years
29:09 - How vendors differentiate beyond product
33:30 - The croissant campaign breakdown
45:50 - 15 AI experiments per week
47:10 - Analyzing prospects via video AI
48:29 - Building AI culture in your team
52:39 - Book recommendations

Guest: Sam Senior, Founder and CEO TestBox
Linkedin: ⁠https://www.linkedin.com/in/samuelsenior/⁠
Test Box:⁠ https://www.testbox.com⁠

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

Newsletter:⁠ https://thegtmnewsletter.substack.com⁠
Visit us on:⁠ https://gtmnow.com⁠
Follow us on LinkedIn: / gtmnow
Follow us on X (Twitter):⁠ https://x.com/GTMnow_⁠ 
Follow us on YouTube: / @gtm_now 
Follow us on TikTok: / gtmnow_ 
Follow us on Instagram: / gtmnow_

AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.
Sam, Founder and CEO of Test Box, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.
If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.
What we cover:
Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)
The shift from discovery calls to validation calls, and how to prepare
CEO (AI-version of SEO): how LLMs are shaping what buyers believe about your product
The "day one shortlist" shrinking from 3-4 vendors to 1-2 vendors
Agent-to-agent procurement: Sam's timeline for when AI agents fully take over buying
Why the mid-funnel is actually getting longer, not shorter
The "Fake Nothing, Prove Everything" campaign that went viral post-Series A
How Test Box runs 15 AI experiments per week across the entire company
Using Google Vertex video analysis to read prospect body language on sales calls
How to build an AI-first culture without burning out your team
Books: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to Great

Timestamps:
0:00 - Cold open
1:09 - What Test Box does
2:43 - How buying has changed
5:48 - What founders/CROs should do now
7:05 - GEO: AI version of SEO
9:02 - Why mid-funnel is expanding
21:17 - Agent-to-agent procurement
26:02 - All procurement by agents in 3-5 years
29:09 - How vendors differentiate beyond product
33:30 - The croissant campaign breakdown
45:50 - 15 AI experiments per week
47:10 - Analyzing prospects via video AI
48:29 - Building AI culture in your team
52:39 - Book recommendations

Guest: Sam Senior, Founder and CEO TestBox
Linkedin: https://www.linkedin.com/in/samuelsenior/
Test Box: https://www.testbox.com
Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
Newsletter: https://thegtmnewsletter.substack.com
Visit us on: https://gtmnow.com
Follow us on LinkedIn: / gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_ 
Follow us on YouTube: / @gtm_now 
Follow us on TikTok: / gtmnow_ 
Follow us on Instagram: / gtmnow_

Auren Hoffman (Flex Capital) joins the GTMnow podcast to share some of the most contrarian takes in tech today, from why AI moats are gone, to why your next VC meeting will be with a bot, to why AI is secretly going to trigger a baby boom.

In this episode:
- Why Auren runs 500+ AI agents to source deals, and what that means for founders raising capital
- The "agent-to-agent" meeting prediction: by end of 2026, first VC conversations will be fully automated
- Why every software moat has been "blown up" and what Salesforce, LinkedIn & DocuSign need to do to survive
- The OpenAI x The Hustle acquisition breakdown: why it's the smartest (and cheapest) distribution play in AI
- Why missing a great deal is 10x more painful than making a bad one, Auren's honest VC mistake framework
- The baby boom thesis: why AI, IVF, self-driving cars & cheaper energy could reverse the fertility decline
- Why companies won't sign yearly SaaS contracts anymore, and what that means for every B2B founder

Auren Hoffman is the founder of Flex Capital, SafeGraph, and LiveRamp. He's an early backer of Replit, Perplexity, Rippling, Vercel, Coinbase, Chime, and AppLovin.

Connect with Max: 
https://x.com/hackitmax
https://www.linkedin.com/in/maxaltschuler

Connect with Auren:
https://x.com/auren
https://www.linkedin.com/in/auren/
https://www.youtube.com/@summationpod

GTMnow shares how the best in tech build, scale and invest.
Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.

GTMnow is run by GTMfund - we are an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.

Chapters:
00:00 - Intro
01:05 - GTMfund Q1 recap 
02:38 - OpenAI x The Hustle breakdown 
06:18 - Redpoint's optimal VC deployment period 
11:24 - Auren Hoffman intro 
13:04 - Why am I seeing this deal? 
26:26 - Sizing up founders at Replit, Perplexity & Rippling 
28:49 - What separates great founders 
32:10 - 500+ AI agents for deal sourcing 
33:40 - Agent-to-agent VC meetings by 2026 
45:13 - Every software moat is blown up 
49:09 - Who kills Salesforce next? 
51:30 - Why no one signs yearly SaaS contracts anymore 
51:50 - AI will trigger a baby boom 
56:22 - Thinking generationally

#AI #VentureCapital #GTM #StartupFunding #AurenHoffman #FlexCapital #SaaS #ArtificialIntelligence #Founders #Sales

Visit us on: 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/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.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.

Wade Foster is the CEO of Zapier, a company that sits between 7,000+ apps and runs millions of automations every single day. That gives him a front-row seat to how companies are actually adopting AI, not just talking about it.
In this episode, Wade breaks down the exact decisions he made at Zapier to go from 10% AI usage to 97% company-wide, why agents and workflows are not the same thing, and what most leaders are getting completely wrong about AI fluency.

What you'll learn:
The difference between agents and workflows (and when to use which)

What triggered Zapier's internal "Code Red" after GPT-4 launched

The one-week hackathon that took AI adoption from 10% to 50% overnight

The AI fluency rubric Zapier built: Unacceptable, Acceptable, Adaptive, Transformative

Why leaders who aren't using AI are the biggest bottleneck in their companies

How to measure AI ROI: floor raisers vs ceiling raisers

How AI now handles 50% of Zapier's customer support tickets

Wade's personal "advisory council" of AI sub-agents he uses for every major decision

Why building a company today is 10x cheaper but distribution is 10x harder

The truth about fundraising: you're selling your company, not raising money

How Zapier stayed profitable by only hiring when it hurt

Guest: Wade Foster, CEO of Zapier
LinkedIn: https://www.linkedin.com/in/wadefoster/
Company - Zapier: https://zapier.com

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
Newsletter: https://thegtmnewsletter.substack.com

Episode highlights
0:00 - Intro
1:13 - The Seinfeld Quote & Kanye Text story
3:16 - Workflows vs. Agents: What's the difference?
6:09 - Zapier's Code Red moment
8:55 - The hackathon that moved AI adoption from 10% to 50%
12:06 - Making AI fluency a hiring requirement
13:47 - Building the AI fluency rubric
16:40 - Why leaders are the biggest AI bottleneck
18:12 - Revenue impact of going AI-first
22:09 - Would Wade build Zapier differently today?
23:20 - Is Zapier's moat at risk from agents?
24:59 - Staying profitable with minimal capital
28:37 - The riskiest contrarian bet that paid off
31:52 - Wade's 3 personal AI workflows
36:53 - Favorite books for founders

GTMnow is the media brand of GTMfund, sharing go-to-market insights from working with hundreds of portfolio companies backed by 350+ of the best GTM executives.
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