Episode Description:

Kyle Parrish was the third sales hire at Dropbox and the founding sales leader at Figma, where he scaled the business from $2M to $950M in ARR over six and a half years through their IPO.

Before Figma, Kyle opened Dropbox's Austin office and hired 150 people in under two years. He's now advising and investing in top AI-native startups.

Kyle is one of the most thoughtful go-to-market leaders in the game - his frameworks on PLG-to-enterprise, founder-led sales, and building high-performing teams are pure gold.

Also, shout out to our awesome sponsor for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're terminally on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day.

Discussed in this episode:

How Kyle spotted Figma before anyone else: the three trends that signaled a breakout
Why PLG companies should consider hiring top-down enterprise sellers, and sometimes not "PLG sellers"
The real reason early customers buy: they're betting on the founder and the dream, not the product
When founders should hire a head of sales vs. starting with individual reps
Opening Dropbox Austin: hiring 150 people in under two years and building the GTM hub from scratch
The founder-led sales trap: why pitching too early kills deals
"Stay low at the highs, high at the lows": how to survive the emotional roller coaster of startups
What most founders get wrong about discovery (and why three boilerplate questions won't cut it)
Building your network like a bonsai tree: intentional cultivation over years, not transactional asks
Why the best early-stage sellers are "evangelical" - and what that actually looks like
The FOMO trap: why comparing yourself to companies on a sugar high will wreck you
What Kyle would tell his younger self after 15 years in startups: stress out less, the score takes care of itself

Episode Timestamps:

(00:00) Kyle's Journey: From Dropbox's Third Sales Hire to Figma's Sales Leader

(06:00) When Should Founders Hire Their First Head of Sales?

(12:00) The Hardest Part of Founder-Led Sales Transition

(18:00) PLG to Enterprise: Why You Might Want the Top-Down Seller

(24:00) Building Dropbox Austin: 150 Hires in Under 2 Years

(30:00) How Kyle Spotted Figma Before Anyone Else (The 3 Trends)

(36:00) Scaling Figma from $2M to $950M ARR

(42:00) "Stay Low at the Highs, High at the Lows" - Surviving the Roller Coaster

(48:00) Why Founders Pitch Too Early (The Discovery Trap)

(53:00) What Kyle Would Tell His Younger Self

About The Vibescaling Podcast:

The Vibescaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host ⁠⁠Chris Balestras⁠⁠, partner @ ⁠⁠Vibescaling⁠⁠ (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About Vibescaling:

⁠⁠Vibescaling⁠⁠ is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.

Where to Find VibeScaling:

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