Stripe’s Jeanne DeWitt Grosser on Buffalo, Whales, and Scaling Sales

May 12, 2021

When Jeanne DeWitt Grosser joined Stripe in 2016 as Head of North American Revenue and Growth, the company was only six months into the process of hiring people with the formal “account executive” title. Up until that point, there had been no formal sales organization—no inbound demand or repeatable motion with large companies that could fuel high growth rates.

What Stripe had in its favor, though, was a lot of success with startup founders (a segment that remains very important to Stripe), and two founders—the Collison brothers—who were personally invested and dedicated to engaging prospects.

“John and Patrick were always on the front lines, talking to customers, helping them get live, and helping them make decisions. So, on some level, Stripe had been doing sales since the get-go—just not in a formal way,” Jeanne explained.

Related read: How Stripe Built a Sales Organization to Successfully Sell to Developers

Even after the company made its initial sales hires, there wasn’t a strong underlying process or motion in place to support predictable growth. “In the beginning, it was just smart people talking with customers and trying to be helpful,” Jeanne said. “But we weren’t at the stage of figuring out if you were going to have a hundred smart people doing that, how do you ensure they’re all doing the same thing?”

In just five years, she’s helped grow Stripe’s sales team to about 200 folks in the U.S. and 500 globally—that’s bigger than the entire company was when she first came on board. Jeanne stopped by the BUILDing To Boss podcast to share some specifics about how she scaled Stripe’s sales organization by focusing on segmentation and role specialization. Listen to the episode below, or scroll down to read the rest of this story.

Getting started with an operating model and the “buffalo strategy”

A lot of Jeanne’s initial work in year one was about helping the company understand an operating model. She needed to get everyone’s head around defining and refining variables like the number of leads, conversion rate, and average deal size. She also spent a good deal of time digging into the work that had already been done in order to uncover important patterns that could be used to create playbooks and other sales assets.

At the same time, she was exploring where it might make sense to develop specialized sales roles so that team members could focus on getting really, really good at their respective jobs. She knew from experience that the jack-of-all-trades approach wasn’t an effective way to scale.

To get the ball rolling, Jeanne and her team implemented what they called the “Buffalo Strategy,” a kind of stepping stone to get to the massive enterprise customers known as “whales.” In 2016, Stripe didn’t yet have a product to sell into huge enterprise organizations, but they did have one that was perfect for Series C and Series D companies, which they referred to as “buffalos”—not as big as whales, but still pretty big.

The Stripe product has matured from those modest beginnings, allowing the sales team to pursue larger and larger “animals.” They graduated from buffalo to what they called a “fin”—not an entire whale organization, but a piece of one. The goal was to figure out how to go from being really excited when a company like TaskRabbit signs on to being able to reliably land 30 TaskRabbit-sized customers every single quarter, over and over again.

Building on initial success with segmentation and specialization


“The first thing we had to do was get smarter about segmentation,” explained Jeanne. “You know you have a segmentation problem when the same account executive is talking to a million-dollar company in the morning and a billion-dollar company in the afternoon. Those sales processes have nothing to do with one another.”

As the company evolved, so did the customer. Jeanne needed to organize the sales team around the new reality. This meant adding more specific segmentation each year, starting with company size, and then adding on additional elements such as the vertical or business model. It’s all about pattern recognition.

Role delineation/specialization

At the same time she was segmenting customer audiences, Jeanne was also looking at ways to build a more effective and scalable sales team by defining roles more clearly. “There’s a big difference between selling to a larger, more complicated user who’s ripping out existing infrastructure, and a Series A company,” Jeanne said. “One requires a specialized team with technical skills, the other you can point to your documentation and away they go.”

While the way SaaS companies structure their sales organizations is constantly evolving depending on market demands and other factors, defining roles based on the customer lifecycle is always a pretty effective approach. Today, the Stripe sales team consists of many specialized teams:

  • An outbound prospecting team
  • A team to qualify inbound demand
  • An account executive team (including a subset team that focuses exclusively on green-field acquisition opportunities)
  • Teams who work with larger, more complicated customers (this group includes implementation teams)
  • Account executives who work with live customers
  • A customer success team to support Stripe’s largest users

And all these specialized sales roles tie back into the segment piece as well. There are, for instance, sales roles specific to startups, mid-market, enterprise, or global prospects. It’s all about giving sales team members the opportunity to hyper focus on doing one thing so that they can do it really, really well, and in such a way that Jeanne can uncover critical patterns on which to build those replicable, predictable pipelines and processes.

More wisdom from Jeanne

Jeanne has done a great job of not only finding companies with massive growth potential, but also getting in there and helping them reach that potential with smart, effective strategies for scaling sales.

To hear more, including insights about how to succeed in an engineering-centered company and advice on revolutionizing the idea of personalization and sales outreach, check out the full episode on Apple Podcasts, Spotify, or our website.

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.