logo
episode-header-image
Jul 2022
52m 1s

20 Sales: The Biggest Challenges Buildin...

Harry Stebbings
About this episode

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?

Up next
Today
20VC: Daniel Gross and Nat Friedman: Acquired by Meta | OpenAI’s SBC Bombshell: More Stock Comp Than Revenue | Privat Equity is Back: Olo Bought for $2BN | Microsoft Lays Off 9,000 People: Is This Just the Start | Will Sequoia Part with Shaun Maguire
Agenda: [00:00] The AI Talent Crisis No One’s Ready For [03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta [12:00] Meta’s AI Talent Magnet: Will It Actually Work? [15:00] Cursor Is Breaking the Market: Can Anyone Compete? [18:30] OpenAI ... Show More
1h 7m
Jul 7
20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical
Scott Galloway is a Professor of Marketing at NYU Stern, where he’s taught for over two decades. He’s the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He’s a New York Times bestselling author of four books ... Show More
1h 10m
Jul 3
20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents
AGENDA: 00:00 – $400B in AI CapEx: Rational Investment or Madness? 05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal. 08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva? 16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 21:30 – ... Show More
1h 11m
Recommended Episodes
Mar 2023
The Business Development Assembly Line Sales Strategy | Andy Buyting - 1654
Don’t ever let anyone tell you there’s nothing new under the sun. Thought leaders don’t approach the world or their industry that way, so why should you? In this episode, Donald Kelly connects with Andy Buyting – coach, professional speaker, and best-selling author of How to Win ... Show More
30m 10s
Sep 2022
Mental Selling: The Purpose-Driven Salesperson, with Lisa McLeod
In this cross-over episode, we’re sharing an episode from Mental Selling. This show is produced by Sweet Fish Media. Sales is one of the only professions where we allow it to be defined by the people who do it badly. Top salespeople are ones who earnestly want to improve life for ... Show More
1h 10m
Jun 2016
#396: Attributes of High Performing Sales People
What are the attributes of a high performing sales person?   In this episode, veteran sales trainers Bill Caskey and Bryan Neale talk about developing a personal ethos that involves continuous self improvement. To what degree do you carry a commitment to bettering yourself? When ... Show More
22m 7s
Feb 2024
The Psychology of Selling: Steps to Selling that Work | Grant Mitterlehner
Welcome to this episode of the Wealthy Way podcast with Grant Mitterlehner, a successful sales trainer and entrepreneur with $50M+ in solar sales, as he and Ryan dissect authentic communication in sales, reveal insights on successful sales strategies, and explore Grant's pla ... Show More
1h 15m
Aug 2022
How To Sell Consulting Services (Without "Selling Out") With Andy Paul: Podcast #252
What kind of sales approach are you implementing? Are you sure you're building relationships with your buyers the right way? Join your host Michael Zipursky as he talks with Andy Paul about mastering the art of selling consulting services without selling out. Andy is the author o ... Show More
46m 55s
Apr 2018
SaaStr 173: Lemkin's Lesson on What To Look For In Your First Sales Reps, How to Approach Variable Compensation, The Right Way To Acquire Customers When Starting Paid Marketing and more with Jason Lem
Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS event with over 20,000 of the world’s best SaaS founders and investors attending every year. Jason also invests from SaaStr’s debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, R ... Show More
16m 12s
Jun 2015
#294: Sales Knowledge
How do you effectively manage your sales knowledge? It may seem unimportant compared to other aspects of your process. Have you ever been in a sales meeting where someone hammers you with features and benefits? How about the person who gives you a complete oral history of their c ... Show More
11m 58s
Dec 2023
You’re a New Sales Manager, Now What? Featuring Mike Weinberg
On this episode of the Sales Gravy Podcast, I dive into part two of my conversation with sales leadership expert Mike Weinberg on what new sales managers need to do to get off to a successful start. The information in this episode is so good that you'll want to listen twice and t ... Show More
39m 17s
Jun 2021
Three Critical Characteristics Every Seller Must Have | Donald Kelly - 1460
Does the thought of hiring a new salesperson fill you with fear? Do you dread the interview process and reading through resumes? In today’s episode of The Sales Evangelist, Donald helps expedite the process of finding the perfect addition to your team by outlining three character ... Show More
10m 5s
Dec 2015
#342: Remote Leadership & Sales Culture - Kevin Eikenberry
Does your sales team all work in the same office from 8am-5pm, Monday-Friday? It’s likely you don’t. Veteran sales trainers Bill Caskey and Bryan Neale talk with the expert on managing remote teams in today’s episode. Kevin Eikenberry, founder of the Remote Leadership Institute, ... Show More
29m 10s