Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139

Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating. ----------------------------------------------- Timestamps: (0:00) Intro (01:15) Entry into Tech Sales (03:10) Lessons Learned from Early Career (07:13) Sequencing Sales Hires (09:27) Sales Hiring Process & Profile (13:03) Sourcing Sales Candidates (19:13) Onboarding Sales Reps (29:28) Measuring Success & Performance (33:13) Hiring Mistakes (35:10) Diagnosing Bottlenecks in Growth (42:13) Importance of AE’s Sourcing Revenue (46:19) Outbound Strategies (52:04) Scaling Sales Function with ACVs (54:04) The Role of AI in Outbound (56:30) The Importance of Human Creativity (01:08:46) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Sam Blond We Discuss: 1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR: What are the secrets that very few people know, that led to the success of Brex and Zenefits? What was the single worst sales investment Brex made? What was the best? What are Sam’s biggest tips to people picking the rocketship they will join? 2. Who, What and When to Hire: When is the right time to hire your first sales rep? Should the founder be the one to create the sales playbook? What is the right profile for the first sales hire? Does it matter if the new hire has domain experience? Why does Sam always advocate to hire through network and not recruiters? 3. How to Hire the Best Sales Reps: What are the questions Sam always asks in interviews with sales hires? Does Sam do case studies with candidates? What is he looking for? What are the biggest green and red flags a candidate can show in an interview process? What are the biggest mistakes founders make when hiring sales teams? 4. How to Have the Best Performing Sales Team: What are the three ways to measure the success of a rep in the first 30-60 days? Why does Sam believe most startups are doing outbound wrong? What should they change? Why does Sam believe demand gen is the bottleneck for all companies? What can be done to solve the demand gen challenge? How does outbound change in a world of AI? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Sam Blond on Twitter: https://twitter.com/samdblond Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #samblond #brex #foundersfund #zenefits #cro #founder #venturecapital #salestips #investing #sales #hiring #hiringtips #outbound