Show Notes
Rob’s Background
Rob Saliterman is the VP of Sales at Harvey, the AI platform for legal professionals that's grown from two customers to a $11B valuation in under two years. Before Harvey, Rob spent five years at Stripe leading teams focused on B2B vertical software platforms. Prior to that, he held sales and leadership roles at Snapchat and Google, where he got his start running political advertising sales after a career in government, including time in the White House. Rob got into sales through an unlikely door: Google needed someone who understood politics and could learn digital marketing. He'd never carried a bag before. He has an MBA from Harvard Business School and is one of the few people in AI sales leadership who came up through government and political communications rather than traditional SaaS.
Discussed In This Episode Why he cold messaged Harvey's co-founder on LinkedIn after reading an OpenAI portfolio list (and how he got a reply)Hiring a VP of Sales before hiring AEs: why Harvey did it backwards on purposeThe interview question that gives the most signal: "Walk me through a big deal: how you created it, converted the champion, and closed it" Selling to lawyers who've never bought software before and why testing for non-technical communication matters more than legal expertiseNo champion, no deal (except when it's worth it to slog through without one)Why pipe gen is a muscle memory sport and the first thing reps deprioritize when they shouldn'tPersonalizing demos using a lawyer's own public filings and why lawyers lean in when you give them something to argue withHiring management consultants alongside AEs to solve the change management objection The managing partner test: why consistency and credibility matter more than polishHow Harvey went from five PDFs you could ask questions about to a collaboration platform with 1,000+ customers
Timestamps
(00:00) Intro (07:45) Rob's Background: White House → Google → Snapchat → Stripe → Harvey (08:40) Why He Cold Messaged Harvey's Co-Founder on LinkedIn (10:24) The Moment He Knew Harvey Was Real: A Lawyer's Outside Counsel Test (12:37) Career Path: How a Government Background Translates to Sales (15:16) The Common Thread Across Google, Stripe, and Harvey: Selling Something New (17:14) Hiring a VP of Sales Before AEs: Why Harvey Did It Backwards (21:05) What Makes a Great Harvey AE: Selling to Non-Technical Buyers (27:18) How the Hiring Profile Changed From 10 Reps to 100 (29:59) Pipe Gen at Harvey: Why the Fundamentals Still Work (34:42) Why Pipe Gen Is the First Thing Reps Deprioritize (36:44) Personalizing Demos With a Lawyer's Own Public Filings (40:05) Rev Ops as an Early Hire: Why Harvey Built Infrastructure From Day One (44:34) No Champion, No Deal (Except When It's Worth Breaking That Rule) (49:49) Change Management as a Sales Differentiator (52:00) The Managing Partner Test: Consistency Over Polish (55:19) Where Harvey's Best AEs Actually Come From (58:32) The "Why Now" Interview Question That Separates Good From Great (01:00:00) Wrap + Where Harvey Is Headed
About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (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 Crew Crew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.
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