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Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970

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. ---------------------------------------------- Timestamps: 0:00 World’s First Female Pro Gamer 7:00 Motherhood 13:58 Lessons from George Hu @ Salesforce 18:03 PLG vs. Enterprise Sales 25:52 Does the founder need to create the Sales Playbook? 27:32 Hiring Tips for Sales 38:53 What does good “sales discovery” look like? 41:13 How to Structure Sales Comp 47:54 How to Measure Sales Effectiveness with Long Sales Cycles 50:40 Should you offer discounts to get deals done? 55:47 Which sales tactics have changed? 57:26 Why Stevie Sued Her High School 58:10 Advice for New Sales Leaders 58:25 What would you change about the world of Sales? 58:49 Which company has the most impressive sales strategy? ---------------------------------------------- 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? --------------------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/stevie-case/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Stevie Case on Twitter: https://twitter.com/Kill Creek Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok --------------------------------------------- #StevieCase #Vanta #HarryStebbings #20vc #20sales

Stevie CaseguestHarry Stebbingshost
Jan 24, 20231h 0mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Pro Gamer to CRO: Stevie Case Redefines Modern Sales Leadership

  1. Stevie Case, now CRO at Vanta, shares her unconventional journey from Kansas kid and the world’s first female pro gamer to senior sales leadership at Twilio and Vanta.
  2. She explains how gaming, product management, and single motherhood forged her grit, empathy, and mathematical, strategy-driven approach to revenue.
  3. The conversation dives into PLG versus enterprise sales, when and how to layer sales on top of self-serve, and how to build and compensate early sales teams.
  4. Case also addresses inclusive cultures for parents, value-based selling in a tougher macro environment, and why curiosity, grit, and authenticity now matter more than ever in sales.

IDEAS WORTH REMEMBERING

5 ideas

Founders must be the first sellers and storytellers before codifying a sales playbook.

Early sales is about vision and trust; the founder has to articulate the ‘why’ and prove value before handing it to a sales leader to turn into a repeatable process.

Don’t layer PLG and enterprise sales too early or without clear ownership.

Running both motions from day one often creates customer confusion and internal credit/comps fights; test sales on top of PLG iteratively and with dedicated resources and clear comp.

Start upmarket with focused experiments, not a full pivot.

Vanta inched from SMB into mid-market/enterprise by carving out a separate team, comp plan, and targets—proving the model before fully committing more resources.

Hire hunters with grit and curiosity over big-brand resumes.

In today’s environment you need people who open doors, endure adversity, and run deep discovery; candidates who over-index on guaranteed comp or order-taking usually fail in startups.

The first sales hire must be glued to the founder, not left alone.

They should join every call, hear investor and partner narratives, and learn to sound like a co‑founder; handing them a written ‘playbook’ and walking away is a common failure pattern.

WORDS WORTH SAVING

5 quotes

You can be competent and also just a flawed human being who is uncomfortable and unsure at times. If you can really embrace both of those things, that's the magic.

— Stevie Case

The best way to open people up is to give them comfort with your own vulnerability.

— Matt Golden (as quoted by Stevie Case)

At the end of the day, what you want out of a great comp plan is something so clear that if a salesperson reads it, they understand exactly what they should spend their time doing when you're not in front of them.

— Stevie Case

The first sales hire has to be able to speak as if they were a founder of the company.

— Stevie Case

We are no longer in a growth-at-all-costs world… everyone now has to be a hunter.

— Stevie Case

Stevie Case’s non-traditional career path: pro gamer to CROUsing vulnerability, introversion, and authenticity as sales strengthsSingle motherhood, bias against parents, and building inclusive workplacesPLG vs. enterprise sales: timing, structure, and operating modelsDesigning early sales orgs: first hires, playbooks, and founder involvementHiring and assessing 10x sales talent: grit, curiosity, and discoveryCompensation, spiffs, and managing sales performance in tough markets

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