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She Scaled DoorDash From $9M to $500M, Walked From OpenTable to Fix Hiring | Kate Crane | Ep. 234 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 conversation, Kate and Robin cover: How DoorDash scaled its B2B Drive business from $9M to $500M+, including the operating discipline behind it What DoorDash, Flock Safety, and OpenTable each got right (and wrong) about go-to-market and experimentation Why Kate calls today's hiring process "bot to bot," with AI writing resumes on one side and AI screening tools filtering them on the other What actually gets a candidate noticed when a human never reads the resume Why storytelling, not features, is what makes or breaks global products and teams What Kate would tell her art-history-graduate self after the layoff that reshaped her career Why "choose optimism, have a plan" became a guiding principle through every career pivot Kate Crane is the founder of Direction Over Perfection, a career coaching practice for professionals navigating nonlinear paths. Website: directionoverperfection.com Instagram & TikTok: @directionoverperfection Podcast: Direction Over Perfection CHAPTERS 00:00 Introduction & Kate's Cold Email Story 02:38 Kate's Background: From Fort Worth to Art History at UT Austin 04:29 Laid Off in 2008: From an Art Gallery in Chelsea to Line Cook 10:49 The Lowest Point: When the Rug Got Pulled Out 12:12 Mentors Who Believed In Her: Arden Moore & Elaine Agather 15:43 Joining DoorDash: Driver Side to Merchant Side 19:05 Scaling DoorDash B2B From $9M to $500M 22:12 DoorDash's Operating Discipline: Measure Fast, Kill Fast 23:28 COVID, the IPO, and "Open for Business" 27:45 Who Is DoorDash's Real Customer? The Three-Sided Marketplace 28:41 The "Bot to Bot" Hiring Problem 29:18 What Makes Kate Say Yes to a Candidate Who Looks Weak on Paper 32:42 Where Kate Stands on AI Resumes & Screening Tools 36:22 Spray and Pray vs. Targeted: How to Actually Get an Interview 38:25 Storytelling That Makes or Breaks Global Products (OpenTable Example) 44:28 Why You Have to Believe Your Own Story 49:01 What a Career Coaching Session With Kate Looks Like 51:10 Booking Kate & How Direction Over Perfection Works 51:55 Trading "Permanence" for a Plan B 55:10 "Choose Optimism, Have a Plan" 56:00 Advice for New Grads Entering a Brutal Job Market 59:53 Why Internships and Work Experience Matter More Than Ever 01:01:54 One Sentence Back to Her Art History Graduate Self: "Take More Accounting Classes" 01:02:51 What's Next for Direction Over Perfection 01:04:38 Kate's Closing Message: Believe in Yourself 01:05:03 Robin on AI, the Defensible Zone, and Staying in Control 01:07:54 Closing & Thanks More Related Tags: Kate Crane, DoorDash, OpenTable, hiring strategy, recruitment, talent acquisition, business growth, startup scaling, leadership, executive leadership, HR innovation, scaling startups, business podcast, entrepreneurship, career growth, organizational growth, AI hiring, hiring process, localization fireside chat, LFC podcast #doordash #opentable #hiring #leadership #businessgrowth #startupsuccess #scalingbusiness #entrepreneurship #executiveleadership #talentacquisition #recruitment #businessstrategy #techleadership #careergrowth #innovation #businesspodcast #ceoinsights #futureofwork

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