20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

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.

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?