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20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

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Mar 9, 2022

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Jeanne DeWitt Grosser

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ANECDOTE

Entry into Tech

Jeanne DeWitt Grosser's father worked at IBM for 17 years, inspiring her interest in tech.
A conversation with Clare Hughes Johnson, her first boss at Google, led her to Stripe.

ADVICE

The Founder's Role in Sales

Founders should focus on initial product-market fit and customer interaction.
Hire sales reps with proven skills once customer calls become overwhelming.

ADVICE

Hiring Multiple Reps

Avoid hiring just one sales rep initially to prevent bias and gain diverse perspectives.
Hire 2-3 reps to identify patterns and confirm product-market fit.

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Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

In Today’s Episode with Jeanne DeWitt Grosser You Will Learn:

1.) Entry into Sales:

How did Jeanne make her way into her first sales job in tech?
What did Jeanne learn from her many years at Google about how sales should interact with engineering?
In hindsight, what would Jeanne have done differently/improved from her time with Dialpad?
How did the role with Stripe come about?

2.) The Playbook:

Does the founder need to be the one to create the sales playbook?
When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion?
What are the single biggest mistakes founders make when hiring their first in sales?

3.) The Hiring Process:

How should founders structure the hiring process for their first sales hires?
What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe?
What should be achieved or learned in each consecutive interview?
How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product?
What are early signs of a 10x sales hire? What are red flags to look out for in the process?

4.) Sales Onboarding:

What does the ideal onboarding process look like for new sales hires?
What tasks and duties should all sales hires perform in the first 60 days?
What are early signs that a new hire is not performing to the right standard?
How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
What should sales leaders do to ensure that new hires engage with product and customer success efficiently?