Stripe’s James Dyett on a customer-first approach to sales

Regardless of the industry or the product you’re selling, the old sales playbook is falling short of customers’ expectations. Companies are ramping up their efforts to increase retention and create sustainable relationships with their customer base – and, those who are providing an exceptional customer experience are seeing the biggest impact on their bottom line.

For James Dyett, a customer-centric mindset shouldn’t just be the purview of post-sales departments. After working for GETF, a nonprofit focused on building public-private partnerships to expand access to clean drinking water in Africa and South Asia, James became interested in the business side of things. He went on to get an MBA, started a job as a product manager at Castlight Health, and quickly realized his favorite part of the job was delving into and helping customers solve their problems. Sales, he thought, would do just the trick. And so, in 2016, he joined Stripe, where he’s now the Head of Strategic Accounts for the Americas.

From the very start, James realized sales shouldn’t be about selling a product but rather about aligning your success with the success of your customers – showing a deep understanding of their needs and goals and how you can help them reach them. That customer-first mindset starts at the hiring process and goes all the way to management: How does that plan help the customer? How does that particular sales target relate to meeting their needs? How are you feeding back customer insights to the product team?

In today’s episode, Intercom Chief Revenue Officer Leandra Fishman sat down to chat with James about the how of sales, building long-term partnerships through a customer-centric approach, and, speaking of partnerships, the launch of Intercom’s integration in the new Stripe App Marketplace, furthering our shared commitment to offer personalized, in-context support.

If you’re short on time, here are a few quick takeaways:

• Focus on building services and products that meet your customer’s needs – not just today’s, but also tomorrow’s.
• Communicating bad news early, clearly, and with empathy is the best way to build a long-term partnership with customers.
• Share the customer’s must-haves with the product team. It helps to keep performance at the top and drives attention to the problems they are telling you they need help with.
• Hire customer-centric salespeople. As James puts it, the easiest way to create that culture is to have it walk through the door.
• While sales managers tend to emphasize hard numbers, performance evaluations should also consider other factors: how that number was hit and what problems it solved for customers.

If you enjoy our discussion, check out more episodes of our podcast. You can follow on iTunes, Spotify, YouTube or grab the RSS feed in your player of choice. What follows is a lightly edited transcript of the episode.

Always a salesperson

Leandra Fishman: Hi James, welcome to the show. We are so delighted to have you with us today. I wanted to start by getting a sense of your career journey. Tell me a little about how you started and how you became the head of strategic accounts at Stripe.

James Dyett: Well, thanks so much, Leandra. My story starts in a bit of an unconventional way. For the first five years of my career, I was president of a nonprofit called GETF, which was focused on building public-private partnerships to expand access to clean drinking water in Africa and South Asia. What we did really well was bring corporations that used a lot of water together with foundations and government agencies to fund projects. And over the course of that time, we launched programs that expanded access to clean drinking water for over two million people. The most eye-opening part of that experience was seeing how small businesses were having the most impact on the clean drinking water crisis because they didn’t rely on long-term donor support and could self-fund maintenance and repairs for, say, a broken water well.

I got really excited about business, got my MBA, moved home to San Francisco after 16 years on the east coast and overseas, started a job as a product manager at Castlight Health, and then joined the Stripe sales team where I still am today.

“In a sense, there was this ‘aha moment’ that I was getting back into sales more than I was starting sales for the first time”

Leandra: That’s amazing. First of all, what an important mission, clean water for everyone. I love that you had that experience and that you’ve had a broad perspective on everything from the business aspect to product to now, it seems, the sales side of things. I’d love to hear a little bit about how your role with Stripe came to evolve.

James: When I was at Castlight as a product manager, my favorite part of the job was spending time with customers and understanding their problems. I noticed that the sales folks got to do this all the time and so I realized, at that moment, that I wanted to spend more time in sales.

I also had a realization that the first part of my career in the nonprofit world was fundamentally a sales role. I was speaking to foundations and corporations not about how we can use technology to solve their problems, but how we can address their goals around corporate social responsibility. So, in a sense, there was this “aha moment” that I was getting back into sales more than I was starting sales for the first time. Then, I started looking around at companies. My main focus at the time was not industry – I didn’t know anything about payments. I wasn’t focused on the size of the company or title, but I wanted to go to a place where I would learn a ton from people I respect, and Stripe stood out far and away on that dimension.

Anticipating your customer future needs

Leandra: I love that. The history of sales is that everyone is a salesperson, regardless of role and title. Communicating value and connecting with customers and helping understand how we can solve a problem is something that, when you have that in your essence, really enhances the overall customer experience. And what’s interesting, too, is that you were at Stripe at an early stage. Are there any business lessons you learned from your early days that you’ve kept top of mind and carried with you through the years as you’ve continued to grow as a company?

James: Yeah, there is. And I’ll share one that I think is a bit unexpected or was unexpected to me at the time. In the very early days, we had about a dozen or so sales reps, and at the time, we were more focused on startups and mid-market growth technology companies. We hadn’t sold to large enterprise technology companies, but that was the next segment we wanted to go after. And so, we decided to start a tiger team focused on seeing what would need to be true to move upmarket and trying to get some early wins with customers we thought would be a great fit for the products we had at the time.

“The business lesson for me was that you need to start selling to where your customers are going to be, not just where they are today”

Effectively, our goal was to go and earn revenue from larger customers, and we were successful there, but I don’t think that’s where we had the biggest impact. We quickly learned that these larger customers had very different needs from our existing install base, but our install base was growing at such a rapid cliff that they were quickly going to have those same needs, and we needed to get ahead of them from a product perspective. And so, that tiger team spent a lot of time with our product team focused on what new features we would need to build to meet the needs of our existing customers.

The business lesson for me was that you need to start selling to where your customers are going to be, not just where they are today. Looking back, that wasn’t what I expected that team would ultimately do, but it’s where we had the biggest impact and, ultimately, influenced our strategy to retain our existing base customers even though the stated goal was to bring in new revenue from much larger users.

Leandra: Such good insight. I think that’s a really important note for everyone, noting the future of that evolution for the customers you have while noting that many times, when you go upmarket, those large customer needs are different than your smaller customer needs, and in general, serving both of those visions for the ultimate customer value and experience will take any company into the right direction.

James: I think that’s right. And that’s where it comes back to sales as a part of product research. We’re the voice of the customer. If you don’t understand a customer very well, one way to understand them better is to go to a sales team and talk to them.

Building trust

Leandra: Absolutely. Being a strategic accounts leader, would you tell me a little bit more about what that role involves and how you think understanding the customer impacts your day-to-day strategy with your team?

James: As head of strategic accounts, I lead a team of sales professionals supporting the companies in the Americas – the United States, Canada, and Latin America. Those strategic accounts are using the Stripe platform in a particularly significant way, and they hold a very, very high bar for payments performance. A big part of my job is working closely with our cross-functional teams to make sure we’re meeting the unique needs of these strategic accounts, who are often bellwethers for what the rest of our customers are going to need because they’re often at the cutting edge of what’s happening in payments or around the commerce ecosystem.

“It’s always going to be challenging to serve the needs of every single customer and do so at the same bar that you hold yourself to and have held yourself to over many years”

Leandra: And being that relationship builder, especially at that critical point where you find your customers, are there any challenges you see in your role?

James: Oh, absolutely. We work with millions of businesses at Stripe and their success is our success. And by virtue of that scale, it’s always going to be challenging to serve the needs of every single customer and do so at the same bar that you hold yourself to and have held yourself to over many years. I see my role in this high-growth environment as ramping, coaching, and mentoring all of the new sales professionals joining our team and making sure we continue to hold a high bar for the success of these new customers. And that’s hard when you’re scaling really fast. These are great problems to have, but it’s a crucible moment for any company – how do you handle that hyper-scale moment? Because if you don’t get it right, you risk losing the trust of the customers you’ve spent so long trying to earn.

Leandra: Yeah. I think what you have really nailed is the word trust. That’s so much at the heart of building great customer relationships. Are there any golden rules or tips you found successful in communicating with clients and customers?

“I’m really passionate about what Stripe builds, and I want to talk about Stripe, but that’s not the way to speak to customers and show that you’re user-first”

James: Yeah. And actually, the word trust is one of them. I have two rules for communicating with clients. The first is about building trust. You may have seen in your career, Leandra, that a lot of sales professionals get worried about giving their customers bad news, such as having to delay a feature or not being able to meet them on commercial terms. And so, they’ll often avoid the conversation or try to water it down, but if you communicate early, clearly, and with empathy to customers, those are the moments when you build trust. Those are the most important moments in building those relationships with customers and growing a partnership over the long term.

Number two is always starting with the customer’s challenges or aspirations. A big mistake we can all fall into as sales professionals is we want to talk about our product or solution. We’re so passionate about it. I’m really passionate about what Stripe builds, and I want to talk about Stripe, but that is not the way to speak to customers and show that you’re user-first. Everything that comes of your mouth should be about how you can solve their problems. You should be able to demonstrate that you understand their problems. They’ll remember it and see that you’re aligning your success with their success, and that’s going to create a virtuous cycle for you as a salesperson.

Customer-first culture

Leandra: I think your articulation of connecting to the customer challenge, the customer pain, and how we’re going to solve their problems as any vendor or partner would want is critical. Especially, as you mentioned, about building the right product. When you think about product innovation and the intersection of that with customer needs that create deeper relationships, what factors go into you giving that information back to your product teams so you can make sure you’re really driving to build the right things to meet those needs?

James: This is, I think, one of the most important jobs of a sales professional. And it’s one we don’t talk much about. How do we guide our product teams to build things that our users are going to love? I have a few rules I keep in mind when I’m speaking to product teams. The first is that we always have to remember the must-haves. We have to keep an incredibly high bar for performance and reliability, even if that means postponing a launch or rewriting a webpage. It’s always important to think about the worst thing that could happen to a customer if we don’t meet their needs around performance and reliability. That’s something that salespeople can communicate to the product team, and it has to be a P zero in the innovation process.

“The easiest way to create that culture is to have it walk in the door every time you add a new person to your team”

The second is we always need to be listening. Instead of dazzling a a user with a product they’ve never thought of, we zoom into those mundane, everyday challenges and help them perform functions that they maybe haven’t been able to perform without your solution in the past. It’s those two things that I think you can keep in mind when you’re speaking to the product team. First, the product has to be reliable. It has got to work all the time. And second, focus on the specific problems that users are telling you they need help with rather than some product innovation that’s a function of a lot of internal excitement but hasn’t been vetted by the market.

Leandra: I think highlighting that customer success and customer service mindset is what sets good companies from great companies apart, and empowering those teams isn’t easy. Do you have any advice for companies that want to foster that amongst their sales and product teams?

“Managers tend to focus on the numbers and that’s an inevitable part of sales, but we should also be framing feedback about the how of sales”

James: You have to hire for those values and make that part of your interview process. Every time somebody on your team is talking to a prospect, you should be testing if they are user-first. Are they humble? Are they curious about customers they’ve worked with in the past? And when you’re discussing whether to hire somebody, that should be a big part of it. Is this somebody that I can picture with a customer-first mindset when they join our team? Because the easiest way to create that culture is to have it walk in the door every time you add a new person to your team.

The second is to make sure that the customer-first mindset is part of regular performance management. Managers tend to focus on the numbers and that’s an inevitable part of sales, but we should also be framing feedback about the how of sales. And that means, yes, “Did you hit this number?” But also, “How did you hit this number? What problems did you solve for your customers, and what problems are you going to solve for your customers this next quarter?” That needs to be a big part of how performance management happens.

And then, finally, when you’re a manager and you’re reviewing an account plan, always ask: how does this help the customer? I’m surprised that simple question ends up really refining and improving how we show up as a sales team for our customers. Even if it’s something we think about every day, asking the question leads to some great conversations and it allows us to change our approach and think, “Well, actually, we could help the customer more if X, Y, Z.”

A one-stop-shop for transactional support

Leandra: I’m really excited to talk to you about the recent news that Intercom has launched one of the first apps on Stripe’s new app marketplace. And I would love to hear you tell me a little bit more about the Stripe app marketplace and what you know about the Intercom integration.

James: Absolutely. Stripe has been working with partners for a long time, but Stripe apps is a step-change in how we do that. And effectively, what it means is we can bring an array of tools together and create a one-stop-shop for managing operations related to Stripe with an ecosystem of partners.

The Intercom app integrated into Stripe allows customers to investigate issues, answer payment queries, approve refunds, and much more. So what does that look like? For example, a customer support agent using Stripe could see a customer requesting a refund through Intercom. They could issue the refund through Stripe and even use Intercom’s app to reply to the customer directly to let them know that the request has been completed. So you can imagine that, as a customer, it’s such a great experience to say, “I’d like a refund,” and then to have that executed in real-time and get a note from a customer service agent through Intercom. We’re thrilled about the 1+1=3 potential of the Intercom and Stripe partnership.

Leandra: The power of that seamless experience is going to get people really, really excited. And I know one of the reasons that Stripe chose Intercom as a launch partner was because of our shared commitment to personalized, in-context, customer support.

“We’re the core infrastructure for businesses to be successful, and we’re successful when our customers are successful”

James: Yeah, absolutely. To compete in the internet economy, businesses are going to have to use a wide variety of software tools. They’re going to need Intercom, they’re going to need Stripe, and they’re going to need a whole host of solutions so that they can focus on the core differentiator for their businesses. From my perspective, integrating with Intercom is just one step to providing that one-stop-shop for managing operations, facilitating automated sharing of contextual information across apps, keeping systems of record in sync, and giving users a fuller view of their business.

I think we see the world very similarly – we want to make it a lot easier and provide this underlying infrastructure. And I think that’s what makes Intercom and Stripe so similar as businesses. We’re the core infrastructure for businesses to be successful, and we’re successful when our customers are successful. We’re behind the scenes, and I love that about our businesses.

“A lot of time on my side is spent on understanding what our customers are most focused on right now”

Leandra: Making it easy for customers to serve their customers is going to go a long way as we continue to see the changes in technology in our environment, so it’s exciting work to be doing together. What’s next for you? Do you have any plans or projects this year?

James: Well, 2022 has been quite a year. We’re really laser-focused on how we can help our customers through a tricky economic period. A lot of time on my side is spent on understanding what our customers are most focused on right now – navigating this year with inflation, the changes in the fundraising market, consumer sentiment. We want to be a partner for them there, and so we’re spending a lot of time trying to think about how we can be helpful.

Leandra: Each year, it seems, brings a new set of adventures and hopefully opportunities for, like you said, helping our customers solve whatever problems are on top of their minds. Everything we can do to make it easy for them to navigate through these times is going to be essential. As we wrap up here, I’d love to know where our listeners can go to keep up with you and the work that you’re doing at Stripe.

James: You can learn about the latest updates on stripe.com/newsroom/news or our Twitter account. You can say hi on Twitter; we’d love to hear from you. And thanks so much, Leandra. I really enjoyed the conversation.

Leandra: James, thank you. I really enjoyed chatting with you today.