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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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Jan 25, 2023

Stevie Case, the CRO at Vanta and former VP of Mid-Market Sales at Twilio, shares her journey from pro female gamer to sales leader. She discusses why startups shouldn't juggle Product-Led Growth and enterprise sales simultaneously, offering insights on transitioning gradually. Stevie also emphasizes the importance of inclusivity for parents in the workplace and advocates for transparency in sales comp plans as a way to motivate teams. Her unique perspective blends professional resilience with a personal touch, making her story truly inspiring.

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ADVICE

Testing Enterprise Sales

Test the transition to enterprise sales by adding sales resources to existing PLG customers.
This helps determine if a sales presence increases revenue and customer satisfaction.

ADVICE

The Sales Playbook

Founders should develop the initial sales story and vision, while sales reps focus on repeatable steps.
This allows for iteration and avoids premature commitment to potentially flawed strategies.

ADVICE

First Sales Hires

Hire one or two strong enterprise salespeople or a player-coach who understands scaling velocity.
Founders must stay engaged and work closely with the first sales hires to ensure success.

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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?