Kate Crane went from an art history degree and a 2008 layoff to scaling DoorDash's B2B business from $9M to $500M+, then on to Flock Safety and OpenTable. Now a career coach, she joins Robin to break down the "bot to bot" hiring problem, what it takes to get noticed when AI screens your resume, and why storytelling makes or breaks global teams.
Kate Crane studied art history, got laid off six months into her first job during the 2008 financial crisis, and talked her way into a job as a line cook before rebuilding her career through an MBA, management consulting, and a run at DoorDash that took its B2B Drive business from $9 million to over $500 million in revenue.
She went on to lead strategy and operations at Flock Safety, run go-to-market strategy at OpenTable, and is now the founder of Direction Over Perfection, coaching the next generation through nonlinear career paths.
In this episode, Kate and Robin discuss the "bot to bot" hiring problem, where AI writes resumes on one side and AI screening tools filter them on the other, and what it actually takes for a candidate to get noticed when a human may never read their resume. They also cover the operating discipline behind DoorDash's growth, why storytelling makes or breaks global products, and Kate's advice for new graduates entering one of the toughest job markets in decades.
Watch the full video conversation here: https://youtu.be/tZTz5cF7au4
Connect with Kate Crane:
Website: directionoverperfection.com
Instagram & TikTok: @directionoverperfection
Podcast: Direction Over Perfection
SHOW NOTES / CHAPTER MARKERS
00:00 Introduction & Kate's Cold Email Story
02:38 From Fort Worth to Art History at UT Austin
04:29 Laid Off in 2008: Art Gallery to Line Cook
12:12 Mentors Who Believed In Her
15:43 Joining DoorDash: Driver Side to Merchant Side
19:05 Scaling DoorDash B2B From $9M to $500M
27:45 Who Is DoorDash's Real Customer?
28:41 The "Bot to Bot" Hiring Problem
32:42 Where Kate Stands on AI Resumes & Screening Tools
36:22 Spray and Pray vs. Targeted Job Search
38:25 Storytelling That Makes or Breaks Global Products
49:01 What a Coaching Session With Kate Looks Like
55:10 "Choose Optimism, Have a Plan"
56:00 Advice for New Grads Entering the Job Market
01:01:54 One Sentence Back to Her Art History Graduate Self
01:02:51 What's Next for Direction Over Perfection
01:05:03 Robin on AI, the Defensible Zone, and Staying in Control