For thinkorswim, innovation starts with listening

May 20, 2024 Chelsey Sleator
How Chesley Spencer improves trading experiences for clients by listening to their needs

Chesley Spencer describes his role as head of product management for Schwab’s suite of trading platforms, including thinkorswim,® as being the hub of a wheel with many spokes. Every day he’s at the center, keeping several different stakeholders (aka spokes) aligned to create a world-class trading experience. He’s helping strategists and business leaders understand the capabilities of technology, and helping engineers and tech leads understand the needs of clients and of the business. All the while shepherding everyone toward the ultimate goal of innovating on behalf of traders and improving the trading experience.

“What my role definitely isn’t, is being the guy that says, ‘This is everything that thinkorswim is going to do,’” says Chesley matter-of-factly.

That’s because good innovation starts by listening.

Yes, you need a vision of what the product should be, but Chesley says it’s also important to stay out of your own way and not push too hard toward a particular outcome without taking direction from your users.

And there’s many ways Chesley listens. There’s feedback from client support reps and investment consultants, there’s client surveys and studies, and there’s also direct platform feedback. But he says you must be careful about how you listen too—you can’t just go around chasing a bunch of soundbites.

“You need to figure out what problem clients are trying to solve for when they tell you a piece of feedback,” he says. “You have to try and figure out the issue at play, try to figure out their mental and behavioral models, which then gets at the UX and design experience to solve the problem.”

Staying close to those that matter

One way to understand the client mindset is to get as close to them as you can. So Chesley’s built a team of product managers with deep expertise and knowledge, many of whom come from a background in client trading support and have talked to thousands of clients over the years.


That’s one of the most important things I hire for—people who understand our clients.

- Chesley Spencer, Head of Product Management for Schwab trading platforms

In fact, that’s how Chesley started his own career. After college he bounced around trying different things, but nothing felt right. When he learned that Ameritrade was hiring phone reps he thought, “Well that sounds like it will include a paycheck,” and gave it a chance. And it turned out he was good at it, earning high marks on the Series 7, or General Securities Representative exam.

Then Ameritrade bought thinkorswim. It was a transformative merger and integrating such an innovative company really lit something up in Chesley, and he thought, “maybe there’s something cool here beyond the phones.”

So when thinkorswim was looking for client support for active traders, Chesley raised his hand. And then, because he was one of the few people who knew both the Ameritrade side and the thinkorswim side, he was asked to work on a project outside of the call center, going through a list of 1,500 potential product issues related to the integration to figure out which ones were actually real. It wasn’t exactly exciting work, but it gave him a deep understanding into how the product worked and it was an organic steppingstone to product management.

He gradually took on more responsibility and bigger roles, working his way up to become the primary product owner for thinkorswim, a role he held for 10 years, where he worked hand-in-hand with the tech team, launching new capabilities like Strategy Roller, Chart Describer, and Trade Flash. And now he’s the head of the product team over Schwab’s entire trading platform ecosystem.

“The hardest part of going from running one platform to many, is that I’ve had to step back and let the people I’ve hired do their thing,” explains Chesley. “This company has tens of thousands of people with great ideas. It’s giving them the space to try and execute that can be the challenge.”

More clients = more listening

With the final group of Ameritrade clients having migrated over to Schwab this May, Chesley’s excited about the opportunities ahead.

“Now that we have a combined client base all at one company, we have this huge group of passionately engaged clients to serve, and we get to ask, ‘What’s really needed?’ That’s a tremendously interesting place to be as product manager and as a company—we can all focus our efforts there,” he says.

It’s a larger and more complex group for Chesley to listen to and draw inspiration from. And we can’t wait to see what they come up with next.