20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta


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Stevie Case is the CRO @ Vanta where she oversees Vanta’s go-to-market team to support the company’s rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, Stevie helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio’s enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue. If that was not enough, Stevie is also a Founding Operator @ Coalition Network and a prominent angel investor.

In Today's Episode with Stevie Case We Discuss:

1. ) From World's First Pro Female Gamer to CRO:

  • How did Stevie make her way from pro gamer to CRO? How did her career in gaming make her a better CRO and sales leader?
  • In her early sales career, how did being a single mother with a child impact her approach to sales?
  • What can founders do to make workplaces more inclusive for parents today?

2.) Enterprise or PLG: Which One To Choose:

  • Why does Stevie believe it is not right to do both PLG and enterprise at the same time for startups?
  • How can startups and sales teams move into enterprise selling gradually through testing and without committing a significant budget to an enterprise sales team?
  • How do founders know when is the right time to move from PLG to enterprise? What are the signs?

3.) The Mythical Sales Playbook:

  • How does Stevie define the term "sales playbook" today? What is it not?
  • Should the founder be the person to create the sales playbook? If not them, then who?
  • When is the right time to make your first sales hire? When is the wrong time?

4.) Mastering the Hiring Process in Sales Recruits:

  • How should we structure the interview process for new sales reps?
  • What is the right profile for these first sales hires?
  • How do the best sales talent answer questions and perform in interview processes?
  • How can we really test for grit and curiosity in the interview process?
  • What are the single biggest mistakes founders make when hiring for sales?

5.) Discovery, Discounting, Deal Velocity:

  • With sales cycles being so long, how do you know if enterprise sales reps are good?
  • What is the difference between good discovery vs bad discovery?
  • Should founders engage in discounting to get deals over the line? When does it work?

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