Balancing the Art and Science of Sales, with Jeanne DeWitt Grosser

Seller's Journey Episode 16
Transparent sales process - working together
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Welcome back to the From Vendorship → Partnership podcast, Season 2: Seller’s Journey! 

This season, we’re talking to B2B sales leaders about their experience building winning processes, coaching & scaling teams, and partnering with customers.

Our guest this week is Jeanne DeWitt Grosser, Head of Americas Revenue & Growth at Stripe!

Jeanne has helped build and lead the sales team at Stripe for 6+ years; previously, she led SMB and mid-market sales for GSuite at Google. In this episode, she chats with Ross about her take on common sales leader pitfalls to watch out for, who you should hire as your early sales reps, and other tactics for early stage sales teams.

Listen to the episode here, and get the key takeaways from our conversation below.

📈 What’s the biggest challenge of scaling a sales team from zero to one?

One of the hardest questions to answer here, Jeanne says, is how much to invest and how quickly. If you under-invest in your sales team early, you’ll limit your growth – but if you over-invest, you’ll accelerate your burn.

Two key things to do during the zero to one phase: start building repeatability, and build out your operating model (funnel math). Pattern recognition is key – look for common elements in your customers, your pitch, your sales process, etc. Once you have your operating model and sales process built out, you can continue to plug team members into it as you scale.

“I’m a big fan of the art and science of sales,” Jeanne said. “There’s no excuse for not being quantitative on this.” 

😨 What are common pitfalls that first time sales leaders run into?

Jeanne named three common mistakes that new sales leaders make:

1. Staying in IC mode. If you’re an A+ rep, it can be hard not to continue jumping into deals all the time when you move into a management role. Sometimes, early stage founders even encourage that behavior. Set good boundaries for yourself in your new role (and make sure leadership is aligned) and focus more on managing and coaching instead of executing on deals.

2. Not aligning with your product org or founders. Especially when it comes to your funnel math, you need to make sure different departments are on the same page – so when something is off or needs to be fixed, you’re able to have a productive discussion.

3. Chasing whatever is in front of you. It might be a near runway to make money, but chasing any opportunities you find without discretion isn’t going to help you scale or enable your product team to build for what’s going to win.

👯 What personas should you look for when hiring your first reps?

“I’m a big fan of diversity of background,” said Jeanne. “Each type of person is going to up everyone else’s game.”

For example, you could look for someone who’s never sold before, but is sharp and loves spreadsheets. Someone who has sold for five years and is scrappy to get sales, but still has more to learn. A senior seller who can bring a lot of sales acumen to the table.

Another thing to watch out for: hiring too far ahead of where you are in your company’s lifecycle. For example, a salesperson who has only worked in large, established orgs is probably going to have a much harder time operating in an early stage startup environment.

“Don’t over-invest in any one persona. Sales is a skill to develop, just like writing code,” Jeanne said.

About Jeanne

Jeanne DeWitt Grosser has nearly 20 years of sales & GTM experience, and is currently the Head of Americas Revenue & Growth at Stripe, where she has spent 6+ years helping to build and lead sales. Previously, she was the CRO at Dialpad, and led SMB and mid-market sales in North America, Latin America, and the Japan & Asia Pacific regions for GSuite at Google.