How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon

Evan Cassidy’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 less than $2M 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, B, C, and 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.

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

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) 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, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

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