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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

Jul 20, 2022

Sam Taylor, VP of Sales and Customer Success at Loom, shares his journey through sales roles at Salesforce and Dropbox. He discusses the importance of understanding customer motivations and effective questioning for successful customer discovery. Taylor explains how salespeople should act as 'customer therapists' to build honest connections and highlights the critical traits for hiring the first sales rep. Additionally, he addresses the challenges faced by outbound sales teams and emphasizes the need for strong collaboration within organizations.

52:01

Creator website

Episode guests

Sam Taylor

Highlights

AI Chapters

Episode notes

How to document your prodic experience

01:25

Building an Outbound Team: How to Balance Inbound and Outbound Engagements

01:34

How to Set Agende for Deal Review

01:45

Intro

3min

Navigating Sales Strategies in Tech

18min

Mastering Sales Strategy and Hiring

15min

Seamless Onboarding for Sales Success

9min

Navigating Customer Priorities in Sales Conversations

2min

Navigating Sales Challenges in a Tough Economy

4min

Community-Driven Sales Strategies and the Future of Product-Led Sales

3min

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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