Howdy - happy 2026 y’all!
For housekeeping, a quick note on GTMBA and Vibescaling:
VibeScaling and GTMBA are going in separate directions in 2026
I (Chris) will be writing the VibeScaling blog weekly on this newsletter (https://www.vibescaling.blog/), covering the same topics you've seen the last few months (intersection of AI + GTM + startups), plus shipping the VibeScaling podcast weekly
Julian is taking the GTMBA name and blog, and he'll share more on that tomorrow
If you subscribed before August 15th, you'll automatically be on both lists. Subscribers after August 15th won't be auto-subbed to GTMBA and will just be subbed on this one you’re reading, but you can subscribe to Julian's content here
Julian is still a dear homie and his content will be elite, I’ve learned so much from him this past year & excited to continue collaborating in the GTM space
Now, onto our regularly scheduled programming 🫡
As some of you know, in Q4 2025, we launched The Vibescaling Podcast.
It’s been energizing to do these, and my goal is to ship each week without missing any in 2026. It’s a core part of our Vibescaling media strategy, which you can see here.
You can expect the smartest GTM minds from the hottest companies to talk all things sales, AI, and startups.
Think of it as a baby born from two of my favorite podcasts - the content of 20VC (specifically their 20Sales series) meets the casual vibe of My First Million.
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
Some of our previous guests:
Todd Busler, CEO @ Champify - see writeup here
Raphael Parker, CRO @ Mandolin (former founding GTM hire @ Segment) - see writeup here
Some of our future guests for Season One:
Liam Mulcahy, GTM Partner @ Kleiner Perkins (recorded, shipping next week!)
Pat Forquer, SVP of Revenue @ Legora (recorded, in edits now)
Mike Donohue, CRO @ Maven AGI (recorded, in edits now)
Jack Gashi, VP of Sales @ Avoca (recorded, in edits now)
Tomer Chernia, VP of GTM @ Cursor (recorded, in edits now)
Eleanor Dorfman, Head of Sales @ Anthropic
Sam Warburg, Head of Sales @ Baseten
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM on LI or reply to this email. We’ll keep openings rolling and be super open to suggestions of similar guests.
We film in-person in SF & NYC at legit podcast studios and have hired a post-production agency, so the quality will be high.
And now, onto the episode 🎙️
Links To Sections
VibeScaling Episode 3: Kyle Parrish
Shoutout to Kondo for sponsoring this episode of The VibeScaling Podcast.
Think of Kondo like “Superhuman for LinkedIn.”
It’s saved me countless hours with LI messaging, and you’d have to rip it from my cold, dead hands if you told me I couldn’t use it anymore.
Give them a try, and use this link to get a month free. No risk at all.
If you send a lot of LinkedIn messages, as I do, you won’t regret it.
Kyle Parrish has two of those runs that a lot of us dream of having - being one of the first sales hires at two unicorns (Dropbox & Figma) - he’s someone I’ve been wanting to interview and meet in person for a while.
The intro becomes a little easier when my partner, Cailen (who was the founding AE at Dropbox), was the one who hired him back in 2010.
Kyle has one of the more laid-back demeanors I’ve met in someone of his success (while still having a quiet confidence), and I’m excited to do this piece on him & hope y’all like it as well.
Kyle’s Background
Kyle 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 was an early GTM hire at Dropbox and opened their Austin office, hiring 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.
Interesting Takeaways
Early customers are buying the founder, not the product. In the first deals, buyers are making an evangelical bet. They're buying the dream of where you're going and the people on the team. The core product is almost irrelevant.
Don't hire a head of sales first. Hire reps. Founders want to hand off sales too early by bringing in a leader. You need individual contributors closing deals before you need someone managing them.
Hyper-growth lets you do things far beyond your years. At Dropbox, Kyle opened the Austin office and hired 150 people in under two years with limited experience. Sink or swim, but if you swim, you compress a decade of learning into two years.
"Stay low at the highs, high at the lows." The startup industry is a roller coaster. Don't get caught up in FOMO when other companies are on a sugar high. Focus on your craft, your customers, and your people.
Founders pitch too early and skip real discovery. The trap: three boilerplate questions, jump to demo, push to next steps. It's okay to have multiple calls. Slow down and understand their business.
Build your network like a bonsai tree. Intentional cultivation over years, not transactional asks when you need something. Kyle followed Figma for two years before joining.
Spot breakout companies by following trends, not hype. Kyle tracked three things before Figma: collaboration disrupting every industry, design having a moment in Silicon Valley, and early engineers leaving great companies to join.
Stress out less. The score takes care of itself. Kyle's advice to his younger self: stop worrying about what's happening behind closed doors. Focus on being coachable, learning, and driving the business forward.
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
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
Thanks for reading!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, partner @ Vibescaling - a GTM advisory, recruiting, media, and investing firm, working with seed through series C AI-natives to help them grow.
Where to find Vibescaling:
We work with many of the hottest AI-native startups in different capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.
🫡 cheers,
Chris