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The official CEO.com podcast featuring unfiltered conversations with the leaders shaping our world.
Clint Betts: Andrew, thank you so much for coming on the show. You are the co-founder and CEO of Extend, a fintech company. Tell us about Extend and how you became the CEO and co-founder.
Andrew Jamison: Well, how I got here is a different story, but Extend is an expense management platform.
What that means is we give companies the ability to control who can spend, where they can spend, and how much they can spend before the transaction ever happens. Then we help manage the compliance side of expense management afterward—things like receipts, approvals, visibility for CFOs, and making sure all of that information flows into financial systems at month-end.
Clint Betts: Tell us how you got to Extend. I noticed you spent 12 years at American Express, so you've been in financial services for a long time. At what point did you realize there was a need for this company?
Andrew Jamison: Interestingly, Extend is really a combination of the only two jobs I’ve ever had.
And it’s not because I’m 27—unfortunately, I’m not.
I spent almost 10 years working alongside SAP as a consultant, which gave me a deep appreciation for technology. Then I spent 12 years at American Express, where I learned how financial rails and payments infrastructure actually work.
Extend is really the marriage of those two experiences.
I saw how SAP grew by creating integrated systems and leveraging technologies like EDI. Fast-forward to today, APIs have completely changed the landscape. They make systems more dynamic, more accessible, and much faster.
At the same time, I could see the limitations of physical cards in an increasingly digital world. Businesses needed better controls, stronger fraud prevention, and more transparency around spending.
That’s really where Extend came from.
Clint Betts: At what point did you decide to actually start the company? How did you find your co-founders, and how did you fund the business?
Andrew Jamison: It was really one of those life moments that forces you to reflect.
My father was an entrepreneur. He built businesses in the supermarket shelving industry and was a three-time founder. Growing up, I watched him work weekends and drag the family into warehouses to count inventory.
At the time, I thought I wanted the opposite life.
But people always tell you that you become more like your parents as you get older, and they’re right.
The turning point came when I took a sabbatical from American Express because my mother was very ill. She had battled cancer for decades.
When you step away from work during a moment like that, you start realizing life isn’t a dress rehearsal.
For the first time in years, I had space to think about what I actually enjoyed doing. I realized what I loved most was talking to customers, understanding problems, and building solutions.
That became my true north.
At the same time, I saw several major shifts happening:
More freelancers and contractors were entering the workforce.
APIs were opening up financial infrastructure.
Open banking regulations were changing how data could be used.
And there was a huge underserved middle market that existing solutions weren’t serving well.
The card industry had largely been built for consumers or very large enterprises. But what about companies in the middle?
That opportunity became Extend.
Today, we serve around 8,000 small and mid-sized businesses.
Clint Betts: One thing that has always struck me about fintech is that the best companies often collaborate with the existing financial system rather than trying to completely replace it.
Does that resonate with you?
Andrew Jamison: Completely.
In fact, that’s exactly our strategy.
Companies like Brex, Ramp, and Divi set out to become card issuers and challenge the existing ecosystem.
We took a different approach.
We don’t issue cards.
We don’t underwrite credit.
Instead, we partner with banks and card issuers and make the cards people already have significantly more powerful.
Our philosophy has always been simple:
The 15 or 16 digits on your card should unlock sophisticated software capabilities automatically.
You shouldn’t need to switch banks.
You shouldn’t need a new card.
You shouldn’t need to talk to a banker or an IT team.
We essentially extend the capabilities of your existing financial relationships—which is actually where the company got its name.
Most businesses rely on their bank for lending, treasury services, foreign exchange, wires, ACH, and many other functions.
Why force them to replace those relationships?
Instead, we make those relationships better.
Clint Betts: How are you thinking about AI and how it impacts fintech?
Andrew Jamison: AI is a perfect fit for fintech because AI loves rules.
And accountants love rules too.
So it’s actually a very natural pairing.
Think about expense management. Historically, someone makes a purchase and then manually categorizes it afterward.
AI can do that automatically.
It knows whether something is a meal, a hotel stay, a software subscription, or transportation expense. It knows which general ledger account it belongs in. It knows which department incurred the expense.
The machine can often do it more accurately than a human.
The same thing applies to receipt management.
Our platform allows users to text or email receipts. AI reads those receipts and automatically matches them to the correct transactions.
That removes a tremendous amount of manual work.
Clint Betts: How are you using AI internally?
Has it changed headcount planning or productivity?
Andrew Jamison: Honestly, there are very few tasks today where we’re not leveraging AI.
Whether it’s research, marketing, analysis, planning, or content creation, AI has become a constant companion.
In software development, a huge percentage of code is now generated with AI assistance.
The productivity gains are enormous.
One area I’m especially excited about is analytics.
We’re launching new capabilities where customers can simply ask questions in natural language:
“How did my spending break down in Q3?”
“Show me anomalies.”
“Who exceeded company policy limits on hotels?”
Instead of building reports, users can simply ask questions.
That’s incredibly powerful because it removes the need for technical expertise and puts insights directly into the flow of work.
Clint Betts: How have you funded the company?
Andrew Jamison: We’ve raised venture capital from the beginning.
Our first seed round came in late 2017 from Point72.
Since then, we’ve raised multiple rounds from investors including FinTech Collective, March Capital, B Capital, and Commerce Ventures.
We’ve raised just under $70 million total.
What’s valuable about those investors is that they bring deep fintech expertise and relationships throughout the financial ecosystem.
Those connections matter enormously when you're partnering with large banks and financial institutions.
Clint Betts: How do you think about company culture and the whole remote-versus-office debate?
Andrew Jamison: I think the answer depends on the role.
There isn’t one universal solution, even though everyone wants one.
If you’re in business development and spend all day on calls, I honestly don’t care where you work—as long as you’re successful.
At the same time, I do want those people coming into the office periodically because they hear things from customers that the rest of the organization needs to know.
For product and engineering teams, I think in-person collaboration matters more.
Some of the hardest problems get solved on whiteboards, not Zoom calls.
You walk over, sketch something out, debate ideas, and solve problems together.
That’s difficult to replicate virtually.
At Extend, we generally ask non-sales employees to be in the office three days per week.
Personally, I come in four days per week.
I live farther away than almost anyone else, but I believe leaders need to lead by example.
If you ask something of your team, you should be willing to do it yourself.
Nothing erodes trust faster than saying one thing and doing another.
Clint Betts: What do you read?
Andrew Jamison: I’m actually pretty boring.
I read the Financial Times every day.
And I read the physical newspaper.
Part of that comes from my British background, but I also like that physical newspapers aren’t personalized. Online content is constantly curated specifically for you.
With a newspaper, you discover things you wouldn’t have otherwise looked for.
As for books, one I’m currently reading is Turn the Ship Around! by David Marquet.
The central idea is moving from a leader-follower model to a leader-leader model.
It’s about creating trust, empowering people, establishing clear goals, and allowing teams to take ownership.
That concept resonates with me deeply.
I believe trust is the foundation of everything.
People don’t run through walls for companies.
They run through walls for people.
And that starts with trust.
Clint Betts: How are you thinking about the broader economy and what’s ahead in 2026?
Andrew Jamison: I think businesses have become much more focused on fundamentals.
The era of zero-interest-rate money created some bad habits.
Now companies are paying close attention to profitability, efficiency, and financial discipline.
That’s actually healthy.
We’ve seen some caution from businesses over the past year, but fortunately we benefit from two major tailwinds.
First, our banking partners help drive customer acquisition.
Second, demand for better expense management and financial controls remains extremely strong.
The size of the opportunity has largely outweighed the macroeconomic headwinds.
Clint Betts: Finally, we end every interview the same way.
At CEO.com, we believe the chances one gives are just as important as the chances one takes.
When you hear that, who gave you a chance that helped get you where you are today?
Andrew Jamison: The first person who comes to mind is Nick Keating.
Early in my consulting career, I was struggling.
I was on a very complicated project, I wasn’t performing well, and I received a pretty negative review.
Most people would have looked at that situation and moved on.
Nick didn’t.
He looked at the feedback and said, “I don’t believe this.”
He pulled me onto his team and gave me another opportunity.
The project we worked on ended up winning recognition as the best project in the company the following year.
Nick became a mentor, an investor in Extend, and remains one of my closest friends.
That single decision changed the trajectory of my career.
The other people I’d mention are our friends and family who backed us financially in the early days.
When we first started Extend, investors told us to go raise money from people who knew us personally.
So we raised $250,000 from friends and family.
That money allowed us to hire engineers and start building.
There’s a tremendous responsibility that comes with that.
When people who know you personally put their trust—and their money—behind you, you feel an obligation to make it work.
Those early supporters gave us a chance, and I’ll never forget it.
Clint Betts: Andrew, thank you so much. What an incredible company you've built. Thanks for spending some time with us. We should check in again in a year and see how things are going.
Andrew Jamison: Clint, thanks for having me on the show. I really appreciate it.