Stripe’s Matt Yalowitz on What Sales and Politics Have In Common

Editor’s note: This story was adapted from an interview with Matt Yalowitz conducted by Casey Renner.

Years ago, when I was just starting my career in politics and policy, I would have laughed if you’d told me I’d eventually wind up selling software.

But after working on a few campaigns—including Obama’s Senate run—that’s exactly what happened. I spent eight years at Google, first in Elections and Issue Advocacy, and later as a Public Policy Manager. From there, I followed Google executive Claire Hughes Johnson to Stripe, where I’m now Head of North America Enterprise and LatAm Sales.

Throughout this journey, I’ve seen again and again how the things that matter most when you’re trying to change minds on policy are the same things that matter most to a strong, authentic sales effort:

  1. You need to tell a story that really resonates with your audience, whether that audience is made up of customers or constituents.
  2. You need to listen to your audience and really hear them. You need to understand the pain points that make life difficult on a day-to-day basis.
  3. You need to create a vision for how the work you do or the product you deliver can make someone’s life or job easier and better.

When I joined Stripe, there were only five people on the U.S. sales team. Today, we have hundreds of salespeople globally. I’ve learned a lot over the course of this massive growth. I’ve also been able to apply many of the lessons I learned in the political sphere.

Establishing the importance of sales

Stripe is a product-first company, so you might assume that sales isn’t a major part of the organization. But the truth is that product-first companies still need sales. Like writing code, sales is a specific and unique skill that requires experience and training. The most successful salespeople at Stripe have mastered three complementary competencies:

  1. Core selling aptitude: This includes abilities like good listening and asking the right questions, understanding the nuances of the sales process, and having an instinctive feel for the give-and-take that’s so crucial to a successful customer conversation.
  2. Strategic intelligence: This is the ability to adjust the sales approach to accommodate different kinds of customers, products, and situations. It’s being comfortable going off script, so to speak—thinking on your feet to keep the conversation going in the right direction.
  3. Product knowledge: It seems like it should go without saying, but it’s critical for a salesperson to have a deep understanding of the product. This means not only being able to retain a lot of product information at a high level of detail, but also being able to expand and adapt that knowledge as the product evolves. For instance, today’s sales motion at Stripe is very different from the one we used five years ago because our products have evolved quite a bit.

In the beginning, you might be able to get away with hiring a sales team made up of individuals that don’t have a background in selling but are willing to jump in and figure things out. We took this approach at Stripe in the early days, focusing more on people who could take on a generalist role. These early team members helped us figure out the initial sales motion and how to structure our sales team, measure results, and iterate.

“Like a seasoned politician who knows how to get things done, a sales pro can help you successfully navigate more complex sales conversations and relationships.”

But as your organization matures, and you start segmenting users and going after specific use cases and solutions, you’ll want to hire professional salespeople whose skill level aligns with where your business is and can help bring it to the next level. When an organization invests in sales—bringing on smart, strategic professionals—those individuals can leverage their conversations with frontline customers to help craft the future direction of the business.

Like a seasoned politician who knows how to get things done, a sales pro can help you successfully navigate more complex sales conversations and relationships.

Creating the right kind of sales culture

Once you get to the point of hiring professional salespeople, you’ve got to hire the right ones. In my experience, the best salespeople possess three specific attributes:

1. They’re naturally and consistently collaborative
Sales reps are never successful in isolation. They work best when they are part of a fully integrated team. Establishing and maintaining cross-functional collaboration is particularly critical for modern technology companies because you’re never just selling a product; you’re selling a solution to someone’s specific problems.

To do this well, you must have a deep understanding of the product and how it’s evolving, and you need to understand specific features and use cases and how they apply to different types of customers. The only way to gain and maintain this level of knowledge is to interact on a regular basis with other teams—product, marketing, legal, and so forth. It’s not unlike the collaboration that needs to take place on a well-oiled political campaign in which all the team members—from candidate to campaign manager to fundraiser to volunteer coordinator—need to be in constant communication to keep the polls moving in the right direction.

2. They’re innately curious and have a growth mindset
People who are curious ask questions, and asking questions is a core part of the sales process. Great salespeople understand the importance of asking “why” in order to get a deeper understanding of each client’s unique business, pain points, and needs. Great salespeople also ask questions of the internal teams they work with in order to understand why a product is designed the way it is. Again, just like how a politician who actively listens to their constituents will be that much more successful.

And curious salespeople don’t stop there. They aren’t afraid to ask why things are the way they are and why they can’t be different. These salespeople have the critical thinking skills to connect the dots between what they’ve learned about a customer and opportunities to improve on the product. This penchant for learning, or growth mindset, means Stripe salespeople are always seeking out feedback as well.

3. They’re humble but ambitious 
I stole this one from Claire Hughes Johnson, Stripe’s COO. The combination of humility with ambition is something you rarely see in most sales organizations, but a requirement for selling at Stripe. These people are the nice ones who finish first (and bring the rest of the team along for the ride). They’re humble about their skills, but have no lack of drive or motivation. They’re always willing to go the extra mile to ensure users get the amazing product experience they deserve, and they are always pushing back to make sure we’re reaching our full ambition as an organization.

In the political sphere, these are the candidates who are fiercely passionate without having a big ego. They have big ideas, but they don’t think they have all the answers.

Emphasizing the need for collaboration

I want to revisit the idea of collaboration because it’s so important to sales success. The idea of sharing knowledge and helping to train each other is simple in theory, but can drive profound outcomes in practice. For example, if the sales team identifies a particular product weakness in the course of the sales cycle and then collaborates with the product team to address that shortcoming, they can improve the win rate (and the company’s bottom line).

We are very deliberate and intentional about initiating and sustaining collaboration at Stripe.

We also think strategically about things like how we set up information sharing structures. Every detail matters. For example, instead of defaulting to pinging someone on Slack or email, we encourage sales team members to discuss things in-person with their counterparts on other teams. As any good politician knows, face time is extremely important whether you’re trying to make a statement or solve a problem.

“It’s extra important now to be intentional about not only the fact that we collaborate, but how we collaborate.”

Of course, some of this kind of in-person collaboration isn’t possible in a remote world; but we still work hard to keep our collaborative culture alive. We may not be able to walk over to each other’s desks, but we can pick up the phone. It’s extra important now to be intentional about not only the fact that we collaborate, but how we collaborate.

Defining what it takes to be a sales leader

There are a lot or parallels between sales leaders and their political counterparts. In both arenas, it helps to:

Be curious
Just like the rest of the sales team, sales leaders should be curious. They shouldn’t hesitate to ask upper management the tough “why” questions. They should be curious about challenges that businesses are facing today, and what challenges they might face tomorrow. And they should want to dig into the speed bumps that customers hit as they go through the sales cycle.

Support each member of your team 
A big part of leadership is inspiring and supporting your team members. One of the main reasons a volunteer or staffer joins a political campaign is because they feel like the candidate has the public’s best interests at heart, and—in the long term—supporting that candidate’s policy vision will help them achieve their own goals. In a sales environment, leaders play a crucial role in helping salespeople to not only learn and succeed in their current roles, but also challenge themselves so they can grow their careers.

Create and sell a vision 
Finally, whether you’re a politician solving the problems of government or a sales leader inspiring your team to help customers, you need to have a clear and motivating vision. You also need to be able to articulate that vision in a way that gets your whole team excited and on board. The best sales strategies aren’t made of pie charts and PowerPoint slides. Like the best political stump speeches, the best sales strategies tell a story about how your product can actually make a difference.

“Whether you’re a politician solving the problems of government or a sales leader inspiring your team to help customers, you need to have a clear and motivating vision.”

Looking ahead

2020 was a whirlwind of a year for everyone for so many reasons. If it taught us anything, it’s that the old saying about change being the only constant might hold more wisdom than we originally thought. Truth is, if you’re not changing, something’s wrong.

As we kick off 2021, we should not only expect change, we should demand it. Instead of being forced to change by external circumstances, we should take charge of our own digital transformations so we can adapt more quickly and innovate along the way. Just like the best politicians craft a compelling vision for the future and take the public along for that journey, sales leaders can do the same for their teams and customers.

More resources for sales leaders

Matt Yalowitz
Matt Yalowitz
Head of North America Enterprise and LatAm Sales at Stripe

Matt Yalowitz is Head of North America Enterprise and LatAm Sales at Stripe.
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