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Welcoming Matt Cunningham, Subtotal's New Head of Operations

We're thrilled to welcome Matt to the team.
Cole Wilkes
Cole Wilkes
Cofounder and CEO
Cover Image for Welcoming Matt Cunningham, Subtotal's New Head of Operations

Matt has a strong background in finance and law and will bring a wealth of knowledge to the Subtotal team. Before joining Subtotal, Matt worked at a top law firm, where he litigated high-stakes cases on behalf of Fortune 100 companies. He has a track record of digesting complex ideas and solving difficult problems, and we’re incredibly excited to have him bring those skills to Subtotal.

As Head of Operations, Matt’s role is foundational to Subtotal’s growth. While he’ll oversee core functions like finance and legal, his impact will extend far beyond that—helping shape company strategy, drive cross-functional execution, and ensure we’re operating at our highest potential as we scale. Matt’s ability to bring structure to ambiguity, navigate complexity, and lead with clarity makes him a critical partner across every part of the business.

More about Matt

Why did you decide to join Subtotal?

The company’s extraordinary product and expansive vision. After speaking with Cole and Jordan—who are two of the brightest people I know—and learning about the product they’re building and what it can do, I couldn’t wait to come on board. Subtotal is going to shape the future of commerce and transform the way brands connect with consumers, and I’m ecstatic that I get to be a part of that.

Where do you find inspiration?

Nature. Growing up in the Rockies, I quickly came to love spending time outside, and that connection has stayed with me. Whether it’s going for a hike, mountain biking, or sitting on the beach, being in nature helps me relax, reset, and get new ideas.

Favorite place to visit?

It’s hard to pick just one, but I’ll go with Nepal. My wife and I spent two weeks trekking in the Himalayas a couple of years back and it was incredible. Between the amazing people and the jaw-dropping scenery, it’s without a doubt the most memorable trip I’ve ever been on.

What’s your favorite way to start the day?

With a quick workout. I find that I’m always more focused and productive after I get some exercise in.

If you weren’t in your current field, what would you be doing?

Some part of me has always wanted to be a physicist, and if I were to choose a different career, it would probably be that. I have basically no physics knowledge (other than what I’ve learned from podcasts like Mindscape and Why This Universe), but I’m fascinated by what little I do know, so I have to think I’d enjoy it.

Any advice that’s stuck with you over the years?

Never stop learning. Don’t assume you have things figured out—stay curious, ask questions, and always look for ways to improve.

How do you like to unwind after a busy week?

Hang out with my amazing wife, golf (though not especially well), watch a show (like everyone else, I’ve been watching Severance and am devastated season 2 is already over), or listen to an audiobook (I’ve been on a biography kick lately and just finished Caesar: Life of a Colossus).

Best meal you’ve had recently?

The Steak Au Poivre at Le Diplomate in Washington, D.C. Their Burger Américain is also unbelievable.

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