Eleven Times Running: Boomi Named a Leader in the 2025 Gartner® Magic Quadrant™ for iPaaS      

Five Minutes With Stephen Fishman

by John Bennett
Published May 20, 2025

Stephen Fishman is Boomi’s North America Field CTO. In this role, he helps drive digital transformation initiatives; develops innovative integration, API and digital product strategies; and works with customers to ensure they’re successful with the Boomi Enterprise Platform.

Fishman’s prior experience in the integration and API market includes over seven years at MuleSoft, where his roles included Regional Vice President and Global Practice Lead – Customer Success Strategy and Architecture. With Boomi CTO Matt McLarty, Stephen is co-author of the book “Unbundling the Enterprise: APIs, Optionality, and the Science of Happy Accidents” (IT Revolution).

How do you explain what you do to your friends and family?

I tell people that I’m an advisory consultant who helps large organizations and sometimes small organizations and startups figure out technology and business strategies so they can create new revenue opportunities, save costs, and lower risk.

What led you to this type of work?

A lot of tech people are nerds. I’m a strange nerd, because when I find something interesting — and I don’t know why I’ll find it interesting, it just will pique my interest — and I’m collaborating with somebody who’s a real expert in their field, that kind of situation is like a magnet for me. I will try to absorb everything I can about how this expert comes to their decisions. Why do they do things that way? What’s their method? Who inspires them? What books are they reading? I try to figure all that out.

In my career, I’ve had the privilege to work with some of the best, industry-known people on charting the course for UX, for service design, and for content strategy. I have an MBA. I’m a finance wonk. I did my graduate work on organizational behavior. I say I’m a strange nerd because I don’t just focus on ones and zeros and bits and bytes. I’ve always been much more interested how technology impacts people, so that drove me into a lot of the UX and design and content because that’s what people interact with.

So, to come back to your question, I came to this place of doing this stuff across four or five disciplines, because I wanted to have an impact on how a company brings everything together to achieve its goals. I’ve noticed over the years people say there’s never enough time and money to do things the optimal way, but somehow there’s always time and money to do something twice. I wanted to change that, but in order to change that, you have to know a lot about people about process, technology, finance, design — all these different things — because I wanted to do good work.

Good work has always been my North Star for exceeding expectations, for making people see something and go, “Wow!” I live for the Wow factor.

Given this mindset, what led you to Boomi?

To me, Boomi looked like the organization with the most conviction to create a universal platform that would allow people to plug and play everything together and be really creative in their jobs. I saw that Boomi could democratize information and access to systems in a safe and secure way to unify speed and security and governance all together. And Boomi felt a lot closer to achieving this with all their recent tailwinds and their rising position in the Gartner Magic Quadrant and their recent acquisitions. Boomi seems like a place where not only I could be of impact but the company was also poised to create a major impact. And I didn’t even mention AI! I feel like the company is on the right path to amazing relevance and impact over the next five to ten years. That’s something I wanted to be a part of.

What’s a typical day like for you?

They vary. On some days, I’m working projects focused on most impactful things that we can do for our customers and how we can take our operations to the next level. Some of those projects will be things I do myself, some will be things I do with others, and some will be things I pass off to other parts of the organization.

On other days, I’m speaking at events or meeting with customers directly and helping them see all the benefits of composability and optionality — the idea that companies should make lots of little bets, so they leave their options open when new opportunities like generative AI come along. In short, all the things Matt and I talk about in our book. The message is going over well. In the next three to five years, I think you’ll see organizations agreeing they need to invest in composability from infrastructure all the way out to experience, and that’s where platforms like Boomi, with all its capabilities, fits in.

What might surprise people to know about you?

I’m am AI optimist. I don’t believe that the robot is going to take all our jobs. It’s never worked that way in the past. Every time automation hits an industry, it creates more jobs than it eliminates. I think the same thing is going to happen with AI.

What’s something about you that someone won’t find on your LinkedIn page?

My wife, Kathleen Kelly, is infinitely more interesting than I am. She’s won an Emmy for a public service campaign against child sex trafficking. In 2001, she won the “audience award” as the SXSW Festival Attendees’ Choice for Best Film for “The Journey,” and in 2003, she won Most Memorable Film for the First 10 Years of SXSW for the same film. As for something interesting about me, I’m an excellent dancer. When I was 19, I had the opportunity to tour the West Coast with a group of teenagers. One of those kids was a very good dancer, and he taught me. When we got back to New York City, he and I used to hit the clubs every weekend. So now I’m really good, especially at Hip Hop and West Coast Swing.

OK, final question. What’s your favorite pizza integration?

Pineapple! Easily the best pizza topping!

Read an interview with Stephen and “Unbundling the Enterprise” co-author Matt McLarty to find out more about their views on preparing for turbulent times.

Up Close With Stephen Fishman

Role: North America Field CTO at Boomi

Home: Atlanta, Georgia (originally from New York City)

Education: Bachelor of Engineering – Electrical Engineering, Economics, Georgia Institute of Technology, and Master of Science in Management, Management Information Systems and Organizational Behavior

Career: His extensive technology background includes over six years years at Cox Automotive — Autotrader, where he was director of consumer platforms & services and later senior director of platform services, and seven years at MuleSoft, where he served as director, customer success architecture, then regional vice president, and finally global practice lead — customer success strategy and architecture.

Cool Things About Stephen: After grad school, Stephen worked for six months as a “liftie” (a lift operator for a ski resort) in Winter Park, Colorado. Later, he once spent a day as a production assistant on the set of Oprah’s Favorite Things. He’s a bookworm and reads widely for work and for pleasure, including everything from academic papers to Hannah Arendt to Yuval Noah Harari to James Clavell.

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