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

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_/

Sponsors:
Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund
.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice.

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

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

For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com

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