Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908

ℹ️ EPISODE INFO

Released

July 21, 2022

Duration

56m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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. ----------------------------------------------------- 0:00 Sam's background 1:44 Takeaways from Dropbox 3:18 Can you do product-led growth and enterprise sales at the same time? 5:03 The problem of agency between buyer and consumer 8:33 The Sales Playbook 10:50 Who should create the first Sales Playbook? 12:55 Should you record calls? 14:58 What type of person do you hire as your first Head of Sales? 20:55 Running Inbound and Outbound Sales at the Same Time 24:55 Structuring the Hiring Process for Sales 31:18 Should you use case studies when hiring? 35:37 The biggest mistake founders make when hiring 35:41 Advice on Sales Compensation 37:25 How to onboard Sales Reps at a startup 40:55 When do I need to bring moola in the coola'? 42:37 Early signs you've hired a dud 43:40 Cross-functional engagement in the world of Remote Work 45:42 How to set up a Deal Review 50:07 #1 Reason People won't Buy Loom this Quarter 51:36 What sales tactics haven't changed in the past 5 years? 52:28 The biggest mistake founders make when hiring Sales Teams 52:53 Biggest Advice for New Sales Leaders 54:04 What's the one thing you wish you could change about Sales today? 54:46 What's one company's sales strategy that impresses you? ----------------------------------------------------- In Today’s Episode with Sam Taylor 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? ----------------------------------------------------- #SamTaylor #20VC #HarryStebbings #20SALES #SalesTips #business #loom #dropboxmafia #hiringtips #salesplaybook

🎤 SPEAKERS

• Harry Stebbings

  host

• Sam Taylor

  guest

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Harry Stebbings and Sam Taylor, Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 explores from PLG Roots to Enterprise Sales: Loom VP Sam Taylor’s Playbook Sam Taylor, VP of Sales at Loom and early Dropbox sales hire, explains how product-led growth (PLG) and enterprise sales can coexist, and when to layer in a sales team on top of a viral product. He contrasts rigid “playbooks” with adaptable frameworks, emphasizing storytelling, genuine discovery, and using sellers as ‘workflow therapists’ to deeply understand user behavior and organizational culture.

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