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


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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?