New episode on the Vibescaling Podcast - Evan Cassidy, VP of Sales @ Decagon, one of the hottest AI-natives out there right now in the customer support tooling space.
Really enjoyed this convo with Evan - always love chatting it up with a fellow Long Islander.
Evan was one of the more down-to-earth folks I’ve had the chance to interview thus far + it was refreshing how vulnerable he was throughout (mainly about his losses).
Thank you all for the kind words on the pod - we'll keep shipping these weekly.
See below for past and future guests:
Some of our previous guests:
Todd Busler, Enterprise Sales Leader @ Clay - see here
Raphael Parker, former CRO @ Mandolin (former founding GTM hire @ Segment) - see here
Kyle Parrish, former VP of Sales @ Figma, see here
Liam Mulcahy, Head of Sales @ Parallel (former GTM Operating Partner @ Kleiner Perkins), see here
Pat Forquer, CRO @ Legora, see here
Mike Donohue, CRO @ Maven, see here
Tomer Chernia, VP of GTM @ Cursor, see here
Jack Gashi, VP of Sales @ Avoca, see here
Eleanor Dorfman, Head of Commercial Sales @ Anthropic, see here
Ghazi Masood, CRO @ Replit, see here
Kyle Norton, CRO @ Owner.com, see here
Jason Gelman, GTM Operating Partner @ Primary Ventures, see here
Some of our future guests for Season One:
Jason Miller, VP of Sales @ Unify (recorded, in edits now)
Jaquelyn Goldberg, VP of Sales @ Unframe (recorded, in edits now)
Rob Saliterman, VP of Sales @ Harvey (recorded, in edits now)
Mark Ebert, SVP of Revenue @ Profound (recorded, in edits now)
James White, VP of Sales @ Rogo (recorded, in edits now)
Graham Moreno, VP of GTM @ Parallel
Mark Goldberger, VP of Sales @ Metaview
Roy Matthew, VP of Sales @ Gumloop
Navid Zolfaghari, CRO @ Zapier
Dini Mehta, former CRO @ Lattice
& others from our portfolio companies @ vibescaling
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 for similar guests.
We film in-person in SF & NYC at legit podcast studios and have hired a new post-production agency, so the quality will be high - see below for a snippet in-studio behind the scenes.
Interviewing the awesome James White for this episode, VP of Sales @ Rogo, in our NYC studio in April
Links To Sections
Evan’s Background
Evan Cassidy is the VP of Sales at Decagon, the leading AI-native customer support platform. He joined as the company's first sales hire when it was doing low MMs in ARR.
Now? Decagon is valued at $4.5B, and Evan has been instrumental to scaling the GTM org along the way from a team of ten through Series A thru D.
Before Decagon, Evan held sales leadership roles at Drift and Dropbox (after getting rejected the first time and doing a 10-month stint at Yelp to build his foundation) before reapplying and landing the role.
Before getting into tech, Evan was a competitive rower: captain of Columbia's heavyweight team, two-time US Under-23 National Team member, and spent time at the Olympic Training Center in Oklahoma City.
Evan had an unconventional start to his career after not starting full-time work until 25 that included driving across the country to San Francisco with no job, no plan, and not much money.
His career has been a study in reinvention and in knowing when to throw yourself in the deep end.
Interesting Takeaways
Most successful salespeople hide their rejection stories. Evan got rejected by Dropbox, Retool, Notion, and Sierra before landing at Decagon. But nobody talks about this stuff. The myth of the linear career - VP to VP, always up and to the right - isn't real. Careers are messy, and pretending otherwise makes everyone else feel broken when they don't get the job.
Your job as a sales leader is to pick the right company. You can over-complicate your career with role scope, title, and comp. But every great seller Evan knows ultimately picked a wave to ride. The company you choose is the single highest-leverage decision you make. Get that wrong, and you're grinding uphill for years.
Most people skip the hardest part of company selection: the self-work. Evan's playbook from Never Search Alone: before you start interviewing, talk to 20 people you've worked with and ask what you're great at and where you need to grow. The answers will surprise you. Your superpower is usually something you've underestimated, and hearing it from others gives you the clarity to stop chasing the wrong roles.
If you're not in AI right now, do everything you can to get in. Evan's take: the next 10-15 years, you'll be competing against salespeople from OpenAI and Anthropic for every good role. They'll have the brand. They'll get the interviews. If you're not actively working to get into an AI-native company now, you're setting yourself up to fight from behind for a long time.
Reinvention is the most important muscle in sales. Evan didn't start working full-time until 25. He's been rejected by some of the best companies in tech. But every inflection point in his career came from throwing himself in the deep end - moving to SF with no plan, going to Yelp after the Dropbox rejection, taking a head of sales role at a sub-$2M ARR company. Every time he took the "safe" option, he regretted it.
The internal stuff is what kills companies - not the competition. Evan's seen it over and over: teams that pull themselves apart from the inside because of politics and ego. The market is hard. Competitors are real. But most GTM teams lose because they get in their own way. His focus is cutting out the noise and keeping the team locked in on customers and winning.
Discussed In This Episode
How Columbia's rowing program went from a century of losing to top 6 in the country in two years - and what that taught Evan about building sales teams
Don't let other people define what you can or can't do: the mindset that runs from his rowing days straight through to Decagon's competitive positioning
Why the "work on yourself first" step before a job search changes everything
The rejection stories high performers don't post about publicly - and why they should
What actually makes salespeople put Dropbox, Retool, and Notion on their shortlist - and whether chasing prestige is the right strategy right now
Why turnaround roles look attractive - and why they're almost always a mistake for GTM leaders
Why the AI wave is different than previous waves, and why the window to get on a generational company is narrower than people think
Building a team that's team-oriented AND intensely competitive - and why that combination is harder to find than it sounds
What 21% automation of customer support actually means: the opportunity is still enormous
Timestamps
(00:00) Intro & Evan's story: from rowing to Oklahoma City to San Francisco
(06:16) Columbia's 100-year rebuild in 2 years and how that shapes Evan’s approach to team building today
(11:22) What traits replace "former athlete" for candidates who didn't play college sports
(15:17) Breaking into tech in 2013 and why Dropbox was the target
(20:06) Getting rejected, going to Yelp, and coming back to get the job 10 months later
(25:12) Why most people ruin their job search by skipping the inner work
(28:45) The Never Search Alone approach and the feedback that redirected his career
(33:00) What "feeling stuck" actually feels like and how one moment with an exec coach shifted things completely
(40:50) Joining Decagon with a 2- and 3-year-old and under $2M in revenue
(46:11) The AI bifurcation and why salespeople need to move now
(51:37) What Decagon's GTM culture looks like and who is actually a good cultural fit
(57:15) Building a magnetic organization: what it means, why it matters
(01:01:30) Where customer support automation goes from here
Thanks for tuning in!
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 various capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.
🫡 cheers,
Chris