Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124

ℹ️ EPISODE INFO

Released

March 8, 2024

Duration

48m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

Brendon Cassidy is one of the OG of enterprise sales of the last decade, having advised the likes of Gong.io, Pipedrive, Showpad. Previously Brendon was first Head of Sales at LinkedIn and VP of Sales at Talkdesk. ----------------------------------------------- Timestamps: (00:00) Intro (00:45) Brendon’s Background (03:27) Changing Landscape of Sales (05:36) The Decline of Outbound SDR Model (07:17) Impact of AI on Outbound Sales (09:05) Defining a Sales Playbook (10:36) Importance of Customer Understanding (12:20) How Discovery Should be Like (14:36) Hiring VP of Sales First vs. Sales Reps (15:26) Hiring Multiple Sales Reps at Once (19:32) Structuring the Hiring Process for Sales Reps (23:44) Financial Incentives for Sales Reps (25:24) Common Mistakes in Hiring Sales Reps (27:19) Onboarding Sales Reps (29:05) Firing Sales Reps (29:57) Brendon’s Biggest Mistakes in Hiring (34:27) Deal Reviews (36:47) Dealing with Lost Deals (43:32) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Brendon Cassidy We Discuss:

1. The Early Days and Navigating Through the Dot-com Bubble: How did recruiting prepare Brendon for a career in sales? What impact did the dot-com bubble burst have on his early career? What does Brendon know now that he wishes he had known when he started his career in sales?

1. The Playbook and Hiring The Team: How does Brendon define the “sales playbook”? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire?

1. Discovery and Outbound Are Broken Why does Brendon feel discovery is useless in today’s sales process? Why does Brendon believe outbound will move under the marketing function? How does AI change the world of outbound sales? Why will no great sales leaders join a company that doesn’t have an inbound machine?

1. Onboarding What is the right way to onboard new sales reps? How quickly do you know if a sales rep is not good? What are the signs? What is the right way to measure the effectiveness of sales teams today? What are the biggest mistakes founders make in onboarding sales teams? ----------------------------------------------- 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 Hifive on Twitter: https://twitter.com/hifiveapp 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 #venturecapital #founder #BrendonCassidy #hifive

🎤 SPEAKERS

• Brendon Cassidy

  guest

• Harry Stebbings

  host

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Brendon Cassidy and Harry Stebbings, Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 explores brendon Cassidy Redefines Early-Stage Sales Hiring And Go-To-Market Models Brendon Cassidy argues that most of the traditional SaaS outbound/SDR-heavy go-to-market model is broken, especially in today’s crowded, capital-disciplined market. He believes AI will push SDR and outbound demand generation back under marketing, while great VPs of sales will refuse roles dependent on outbound-led growth. For early-stage startups, he insists that founders must sell first, design the initial playbook, and only make their first 3–5 sales hires through trusted networks, not open-market recruiting. Throughout, he emphasizes deeply understanding buyer psychology, minimizing bloated discovery, running tight monthly sales processes, and hiring for proven grit and coachability over brand-name resumes.

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