Lessons from Google and Stripe: Talking Sales and Product-Led Growth with Jeanne DeWitt Grosser

When Jeanne DeWitt Grosser joined Stripe six years ago, the financial services company had about ten account executives. Today, Stripe has hundreds of account executives and around one thousand go-to-market team members spread out across the globe, making it a prominent player in the global fintech space.

Currently, Jeanne heads Stripe’s Americas revenue organization, where she plays a key role in overseeing the company’s sales acceleration strategy. In this interview, Jeanne lets us in on her career journey in sales, her thoughts on the hype around product-led growth, and her predictions for the future of enterprise sales.

Justin: So, how do you go from studying marketing and the varsity diving team to leading sales at Stripe? Tell us about your journey and how you ended up in sales.

Jeanne: I thought I was going to be a sports marketer until about my senior year of college but had a few internships that I didn’t love. This led me to consider sales, which my father did for a living. He sold for IBM, among other tech companies, and was always traveling and working on interesting things. So I eventually cold-called my way into an internship at a tech startup that made accounting software. My main task was prospecting into accountants up and down the Eastern seaboard. 

After graduating, I changed directions and wound up working in Google’s support organization. I did four years there and then went to business school. When I came back, I was determined to get into sales and joined what is now Google’s cloud organization. This was before “the cloud” was even an industry term. 

I’ve been in sales for about the last 15 years and haven’t looked back.

How did your time in the support role influence your sales career?

First of all, I was fortunate to work on Gmail, which was blowing up at the time. It taught me how to think at scale, which is a key aspect of self-service-oriented businesses.

In addition, I was the main liaison between the support and engineering organizations, which taught me a lot about how to effectively influence and work in very product-led companies. If Gmail had a bug in a certain place or was missing a functionality, those were the two things that drove the bulk of support tickets and queries. 

Both Google and Stripe are very engineering-centric. From a sales perspective, I think it’s very different to operate in engineering-led companies compared to enterprise software companies that are more go-to-market-led.

Sales is fundamentally about solving problems. People ultimately buy from you when they feel you’re going to help them solve a legitimate problem that they have.

That makes sense. I think it’s fair to say engineers aren’t always the biggest fans of sales. What are your thoughts on some of the misconceptions about being in sales? What are some of the upsides of being in sales that people may be unaware of?

There is definitely still a “used car salesman” mentality associated with sales. 

The truth is that excellent salespeople typically know the product better than half the engineers at the company. And they know the market well, too. I always say that the best salespeople and sales organizations are 50% revenue-generating and 50% R&D because they’re out there talking to customers every day. 

I also think that sales is fundamentally about solving problems. People ultimately buy from you when they feel you’re going to help them solve a legitimate problem that they have. So often, I get to dive into someone’s go-to-market strategy, talk to them about it, and identify how Stripe can help grow their revenue along the way. 

What I’m doing is almost like strategy consulting.

There's no reason that you need to have a salesperson engaging with a 10-person company or a simple use case. You don't sell when the internet can sell for you.

Speaking of strategy, product-led growth (PLG) is one of the hottest topics in the enterprise space. How do you define PLG, and what do you think about all the hype around this topic in general?

I would describe product-led growth in two buckets: 

The first is having a well-oiled self-service engine for the low end of the market. There's no reason that you need to have a salesperson engaging with a 10-person company or a simple use case. You don't sell when the internet can sell for you. We were doing this back at Google in 2010 when I worked on Google Workplace, which in my opinion, is the original product-led growth or self-service engine.

The other side of it is the bottoms-up sales concept. Historically, almost all products were bought top-down by a C-level executive. Now, we have IT consumerization where a user puts a credit card down and you can have the groundswell. But if you want to get to a seven-figure deal, you often have to sell to leadership at a certain stage.

Both have implications. In the first camp, there’s a point at which a 10,000-person company is not self-serving to your business. People must realize that and understand the appropriate time to layer in humans.

For the second bucket, you’re also not typically going from a 100-person team to a 10,000-person deployment. So understanding when to layer in a sophisticated sales motion is also important.

How would you recommend companies think about when to layer in sales?

Determining when to let a company self-serve and knowing when and how to layer in humans is critical. There are essentially three buckets of customers:

• Bucket 1: There’s a set of accounts that are “dead on arrival,” usually because they’re outside of our ideal customer profile. It would be a waste of time to dedicate resources to them.
• Bucket 2: Some accounts are self-service and are very healthy. If you put a human on it, all you'd be doing is adding costs.
• Bucket 3: This is where it gets tricky. There's a middle ground for existing self-service customers where we are confident that human intervention will positively impact the outcome. Either we’ll improve their chances to convert, keep them around as a customer, or better yet, grow their usage over time.

Changing gears a bit. Compared to the age of the company, the enterprise sales motion is relatively new at Stripe. How did you start to segment out the team as you saw more traction on the higher end of the market?

The simple answer is we started getting interest from enterprises. While your average enterprise will not fill out your “contact sales” form, every so often, a more forward-thinking enterprise will. So, we started getting at-bats with large enterprises like Pitney Bowes, which led us to build a dedicated enterprise team.

We just couldn’t have someone talk to a two-person startup in their garage at 9 a.m. and Pitney Bowes at 10 a.m. They would have the wrong conversation. In other words, you can’t have the same conversation with those two companies. When talking to a developer, you’ll go deep into API language and geek out on technology. When you’re talking to a company like Pitney, you need to be talking about risk and security and how accounting can close the books and make sure revenue comes in. So, we had to segment the team because the content was fundamentally different.

Looking ahead now, what do you think the role of sales will be in about five years? Will it be drastically different?

There are parts of it that I think are going to stay the same, particularly in the enterprise. Even now in the post-pandemic environment, people still want to meet in person. They want to get in front of a whiteboard and map things out. We’re all comfortable with Zoom, but I don’t see it replacing the upper end of the market with $10 million and $20 million deals. The skills associated with that dynamic like being able to map an organization or figuring out how to get to power aren’t changing either.

I do think what’s changing is the degree to which salespeople need to have legitimate content. It’s not just a relationship-driven sale. At the higher end of the market, you're increasingly seeing sales (and the other functions that support sales) look much more like management consulting. We do these executive visioning workshops that are not all that different from what McKinsey might do.

At the low end of the market, I believe that as you get more immersive demo experiences and ways where people can touch and feel and have a human-like experience without talking to a human you'll continue to see more and more people be able to make purchasing decisions without needing sales engagement. Then sales will either have to move up the market slightly or figure out the incremental value you're adding when you do decide to have a salesperson engage in the lower end.

Last question: What’s your favorite part about sales?

I find go-to-market strategy is very complicated, and in many cases, there are no obvious answers. If you want to do it well, there’s a lot of experimentation. You have to try different things, figure out what’s working, and then double down and scale.

Thank you so much to Jeanne for sharing her insights with us. Be sure to follow Jeanne on LinkedIn and check out open roles on her team at Stripe.

To learn more about how Pace can help your product-led sales strategy, check out our blog or send us a message. We’d love to hear from you.