Max Freeman ’13 Talks About his Start-up Success and the Power of the Alumni Network

When Freeman spoke to students, he noted that he would not be where he is today if it were not for Gunn. Alumni connections opened the door for him to become Ramp’s first sales hire, and his ability to further leverage the Gunn network — combined with his own hard work, commitment, and grit — helped him to land his first clients.

“It all ties together to The Frederick Gunn School. I would have actually never ended up at Ramp had I not gone here,” Freeman said.

The Power of the Network
Freeman spent three years at Gunn and played for the Boys Varsity Hockey team, which earned Elite Eight New England Tournament appearances in his junior and senior years. He went on to earn a degree in economics and play D1 ice hockey at the University of Delaware. He started his career in finance, working as an analyst for UBS in New York, and then as a sales development representative and account executive at Namely. Six years ago, at the height of the global pandemic, he learned about Ramp through a classmate, Dan Barker ’12, whose best friend from home had moved to New York City around the same time. His roommate knew Ramp founders Eric Glyman and Karim Atiyeh.

“You can think of Ramp as a corporate credit card and an expense management platform, but really what it’s doing is helping companies spend less money, which is very counterintuitive for any payments business,” Freeman explained. “That’s OK, because over a very long time horizon, we feel that we’re going to gather more and more market share, and we believe we are the only corporate credit card that is fully layered with AI. We’ve had AI in our product since the very beginning of 2020. AI really had this moment — this tailwind I would say — from late 2022 to now, and so we feel that we were ahead of the curve.”

Glyman and Atiyeh were roommates at Harvard, and after they graduated, they started a company called Paribus. “They effectively do what Ramp does today but for consumers. So imagine on your credit card, you go buy a TV at BestBuy for $500 on a Tuesday, and that same TV at BestBuy is only $400 on a Thursday. Paribus would automatically get you a $100 refund,” Freeman said, explaining that the company grew quickly and was acquired by Capital One.

Two years later, Glyman and Atiyeh launched Ramp to do for corporations and enterprises what Paribus had done for consumers. They quickly found outside investors. “The market that they were going after was massive. They then got to hire their early team. I was fortunate enough to join Ramp as the first sales hire back in March of 2020. I got really lucky,” Freeman recalled.

A Seat at the Table
Asked how he made himself stand out in the hiring process, Freeman said he agreed to take a step back, signing on as a sales development representative (SDR), an entry-level role that he had already been promoted from at Namely. “It’s not easy. You’re effectively eating glass most of your day by making a ton of cold calls. You’re sending a lot of cold emails,” he said, explaining that the challenge was compounded by the fact that, during Covid, the people he was messaging didn’t know if their jobs would exist the next day.  

“The big point that I tried to make with them [at Ramp] was, ‘I don’t care what my role is. I just want a seat at the table and I want to do this.’ Before Ramp, I was a midmarket account executive. I said, ‘Guys, I don’t care what you pay me. I’ll come in and work for free, I just want equity.’ And so I became an SDR all over again, which is a crazy thing to do.”

One of the first calls Freeman made was to another Gunn alumnus, Ben Krall ’06, the founder of Urban Umbrella, a company that designs and builds premium sidewalk scaffolding solutions. Under Krall’s leadership, Urban Umbrella expanded from New York City to 18 cities in the U.S. and Canada. Freeman also knew Krall played hockey at Gunn and at Syracuse University. 

“I just reached out and said, ‘Hey, I’m a former Gunn hockey player. I started working at this company and this is what we are doing,’” Freeman said. “I think he wanted to pay it forward. Low and behold, we got our first customer. They were pretty big. What it did was, it pushed our product and engineering team to then integrate with their accounting system. That helped us get more and more companies. It’s a longwinded way of saying I got lucky in the sale, and I wouldn’t have gotten there if I didn’t attend the school.”

The alumni network again played a role in helping Freeman bring his second customer to Ramp, Quassy Amusement Park in Middlebury, Connecticut. Eric Anderson P’13, the father of Freeman’s classmate, Sam Anderson ’13, is the company’s owner and president.

Another alumnus, Jaren Taenaka ’12, runs the CSM team at Ramp. “These folks are tasked with implementing the product, integrating it into the variety of systems that are needed. It’s a highly technical role. You wouldn’t want me doing that, but you’d certainly want Jaren Taenaka doing that,” Freeman said, noting that Taenaka was the top scholar of their class.

“I actually wasn’t the best student. I was good enough. I went to a decent college. But in hindsight, I think I leveraged the network, and the moment, and truly capitalized on meeting very interesting people who were genuine and kind,” Freeman said, encouraging the students to reach out to him and other alumni as they start their careers. “A lot of other people that are alumni in this network want to do the same. They want to pay it back.” 

Entrepreneurial Lessons
Looking back, Freeman said Covid acted as an accelerant, fueling Ramp’s growth as more and more companies looked to cut their spending. Yet he said the company’s initial target market was unattainable.

“We got this wrong. When I joined Ramp, I think just due to blind optimism, our CEO, who was my boss in the beginning, said, ‘Alright, we’ve got this product, let’s go get Ford, Coca-Cola, Netflix, and Meta to use this.’ I actually broke into some of those accounts and got meetings, only to get [metaphysically] punched in the face and realize we cannot meet the needs and requirements of these massive companies. We don’t have the global capabilities, we can’t integrate with their accounting systems, and so that allowed us to then get really focused on smaller businesses, start-ups, specifically, seed stage Series A, and then gradually, over time, mature the product to then go up-market,” Freeman said, adding: “I think nailing your ICP, which is your Ideal Customer Profile, out of the gates is critical. Let’s say we won Ford Motors by luck. That would have destroyed our engineering team. They would have had to go and build all of this custom stuff. It would have been a disaster. So, dialing in the focus on who you should target is a good point.”

Ramp’s start-up success was also driven by “engineering horsepower that looks like Open AI’s talent roster,” he said. For example, Calvin Lee, who enrolled at MIT in 11th grade and later earned a silver medal in the International Olympiad in Informatics, is Ramp’s Technical Chief of Staff. Its Director of Software Engineering is Veeral Patel, who attended Stanford and developed the Shortcuts app for Apple; and Ramp’s Engineering Director is Pablo Meier, who was a founding engineer for Lyft, Uber’s rideshare competitor.

“The density of talent and the network graft that is available to these people gave us a very unfair advantage out of the gates with selling it to other start-ups, and putting points on the board, and getting quick revenue. We went from zero to $100 million in seven and a half months. I feel incredibly privileged to make this potentially arrogant claim: there wasn’t a struggle because of that.”

A Boost from the Super Bowl
If the name Ramp sounds familiar, perhaps you remember seeing this year’s Super Bowl ad, “Multiply What’s Possible,” featuring actor Brian Baumgartner from The Office as “the world’s most famous accountant.”

Freeman is “a huge Office fan,” and recently met Steve Carell. However, he said it was Ramp’s first Super Bowl ad, which aired in February 2025 and featured Philadelphia Eagles running back Saquon Barkley, that really helped to boost brand awareness. “March and April were our best months ever as a business,” said Freeman, whose networking behind the scenes facilitated Barkley’s appearance.

“I got to have dinner with him two nights before they played the Rams in the [2025] playoff game, if you remember the snow game where he hit his helmet. He’s a huge fan of technology. I’m a diehard Birds fan. I grew up in Philly, so we started talking. I was telling him about Ramp. I asked him, ‘Hey do you want to invest?’ He said, ‘Yes, I’ll give you guys some money.”

Eight days before the Super Bowl, Ramp bought an ad spot from Aflack at a discount, and Barkley filmed the commercial at no cost. “He was an investor in the business,” Freeman said. “He had given us money, and he wanted that to grow.”

This article was originally published in Gunn: The Bulletin of The Frederick Gunn School. 

Photos by Ali Heck Southworth