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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom

Harry Stebbings 52m 46 months ago
The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Show Notes

Sam Taylor is the VP of Sales and Customer Success @ Loom, an essential tool for hybrid and remote teams allowing you to record quick videos of your screen and cam. At Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist, Sales Development, Global Customer Support, Revenue Ops + Strategy and Sales Enablement. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.
In Today's Episode We Discuss:
1.) Entry into the World of Sales:
How did Sam land his first big role in sales at Salesforce?
How did the sales orgs differ when comparing Salesforce to Dropbox?
What are 1-2 of Sam's biggest lessons from his time at Salesforce and Dropbox that shapes how he thinks today?
2.) Sales People Should Be Customer Therapists:
What is the right way to approach customer discovery?
How can sales reps get potential customers on a call in the first place?
What are the right questions to ask? What engenders the most honesty?
What are the wrong questions to ask? What are common mistakes?
How do the best sales reps then feed that back to customer success and product?
3.) The When and The Who:
When should founders consider hiring their first sales hire?
Should this hire be a sales leader or a sales rep? What are the nuances?
What are the characteristics of the best first sales hires?
What are the first sales hires really on the hook for?
Why does Sam disagree with the word "playbook" and instead suggest "frameworks"?
4.) How To Hire The Best: The Process
What are Sam's lessons on what it takes to hire the very best sales reps?
What are the right questions to ask in the interview process?
What tangible case studies or tests are done to measure quality?
Who is brought into the hiring process and at what stage?

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