Adam FastmanVP of Customer Experience
From barns and robots to building world-class support.
Pennsylvania · VP of Customer Experience · Joined 2023
Adam studied philosophy. He restored colonial-era barns. He fixed experimental robots in Cambridge. Now he runs Customer Experience at Files.com — and the function he found here is the one he kept trying to build everywhere else.
When Adam talks about his career path, it doesn't sound like a straight line — it sounds like three or four different lives that all eventually converged at Files.com.
He studied philosophy. Spent years doing barn carpentry in New England, restoring colonial-era structures. Became the “is it plugged in?” help desk guy at a health plan in Philadelphia. Helped support experimental robots at a robotics company in Cambridge. Did sysadmin and consulting work for everyone from small tax firms to state 911 systems. Then moved into SaaS support for a remote role so he could live out in the high desert of western Colorado.
The throughline in all of it: he kept ending up in the role where people called when something broke — and he discovered that he actually liked that part best.
“I realized I like doing SaaS support more than being a sysadmin or network engineer. I like talking to customers, figuring out the hard problem, getting it fixed, and knowing it's really fixed.”
But at his last company before Files.com, there was a ceiling. Support was underpaid, under-resourced, and treated like “just support.” The product had serious flaws, engineering was slow to respond, and a big part of the job was inventing workarounds for known bugs that never got properly fixed.
“I'd basically reached the dead end of my career there. I'd gone as far as you could go in support at that company. And it was clear that was it.”
He wanted something very specific next: a place where support mattered.
Finding Files.com.
In 2022, Adam moved back home to Pennsylvania and started looking for a remote role that would let him keep building a career in support — not just tread water in it. When he came across the Files.com posting, one thing grabbed him immediately: the compensation.
“The salary number was a big deal, obviously,” he says. “But more than that, it signaled something: if they're willing to pay two or three times more than my last company for support, they must actually value it. They must think it's important.”
That was exactly what he'd been missing.
He went through a long, demanding interview season, juggling recruiters, callbacks, and ghosted processes from other companies. By the time Files.com made an offer, he was exhausted — but he also had a strong gut feeling.
“It was a job offer that would drastically change my situation. I didn't know everything about the company yet, but I knew they treated support like a serious function. That mattered.”
He joined as a Support Engineer in early 2023.
Walking into a function with room to grow.
On day one, Adam discovered two things at once: the Files.com product was solid — far more robust than what he'd worked with elsewhere — and the support function itself was still early in its evolution.
“We had a lot of tickets in the queue and not a lot of maturity in the support process,” he says. “But even then, the documentation was miles better than at my previous employer, and it was obvious the company cared about getting support right.”
He was also struck by the visibility and involvement of the CEO. At his previous SaaS company, the CEO was a distant figure he'd see once a month. Here, Kevin was present in Slack, in team meetings, in the details — clearly across the product, the infrastructure, and the support problems.
At the all-company meeting in Orlando not long after he started, Adam saw an even bigger difference: the way the business itself got discussed.
“It was the first time I'd ever had a CEO give that much real detail on strategy, finances, direction — without the usual vague, buzzword-y 'LinkedIn speech.' It was: here's what we're doing, here's what we changed, here's why.”
Day to day, doing support at Files.com was a different job from anywhere he'd done it before. The platform behaved the way it was supposed to. The documentation was something you could rely on. Engineering responded quickly and fixed things properly. Leadership handled tricky tickets before they turned into fires.
“In a lot of places, support is about guiding customers around a rickety platform and hoping it doesn't fall apart. Here, you're standing on solid ground. If something's wrong, we fix it. If our docs aren't good enough, we improve them. The standards are just higher — and we actually have the ability to meet them.”
From IC to VP.
Adam didn't join Files.com in a leadership role. He came in as an individual contributor on the support team, focused on doing excellent work with customers and learning the system as quickly as he could.
He cared deeply about his own output — but he also cared about the overall function. Was the team organized correctly? Were tickets being handled the right way? Were processes evolving fast enough to match what the business needed?
“I wasn't walking around saying, ‘What do I have to do to get promoted?’” he says. “I was just trying to make sure the team, not just me, was doing great work.”
When the company decided it needed more support leadership, the choice was clear. “There were people on the team with more tenure than me,” he says. “But it seemed like I was the one who was naturally taking the most leadership — caring about the whole system, not just my own queue. So they promoted me.”
From there, as the company reorganized and built out new functions, Adam kept stepping into the empty spaces. He's now VP of Customer Experience, overseeing the teams that handle non-sales customer interactions.
“At Files.com, the person who gets it — who understands how to work here, how to communicate, how to care about outcomes — can absolutely pass the person who's just been here longer.”
He now actively looks for the next people to promote. “I'm constantly scanning for, ‘Who can I give more responsibility to? Who can I grow?’ Nothing would make me happier than seeing the people on my team advance and take on more.”
The support function he's proud of.
Support at Files.com today is not what Adam walked into in January 2023. The function has matured significantly. Response quality is higher. Standards are clearer. Customer feedback increasingly sounds like it was lifted from the team's own vision.
He's especially proud of the team itself. Large, complex customer migrations completed with minimal downtime and high trust. Initially skeptical enterprise customers turning into enthusiastic partners. Customer after customer at events like Files.comCon saying, “Your support is the best we've ever had.”
When Kevin called out support as the highest-performing team in the company at an all-hands meeting, Adam wasn't expecting it. “That filled me with joy. It was one of those moments where you can point and say: that's the result of years of work, from a lot of people who care.”
The real time off.
On a personal level, Files.com has changed Adam's life in very concrete ways. “I bought a house,” he says, matter-of-factly. “I spent a really long time underpaid. Just the compensation alone has made a big difference. I'm not constantly scrambling anymore.”
The remote nature of the work isn't new to him — he's been working remotely since 2017 — but Files.com's approach to flexibility, travel, and boundaries stands out. Quarterly in-person company meetings let him actually meet his teammates. Extra hotel nights around the events have turned work trips into short getaways with his partner or opportunities to see long-lost friends. Time off is respected. When he's on PTO, people don't drag him back in.
Even on the on-call side, where there's always the possibility of being paged at odd hours, he feels that his time is valued. “If you get pulled in on a weekend or holiday or late at night, you don't have to go beg for that time back. It just shows up in your PTO bank. Little things like that add up. It signals: we respect your time.”
What he'd tell a candidate.
If someone with a lot of potential asked Adam what it's really like to work at Files.com, he'd say this. You will be working on something real — core infrastructure that businesses actually need. You will have leverage — Files.com can bring on huge customers without needing to build enormous parallel organizations, because the platform and the teams are built to scale. You will have opportunity — especially if you care deeply about your work and you're willing to act like a leader before anyone gives you the title.
“If you care about outcomes, if you communicate well, if you want to make things better — not just for yourself but for the whole team — there's a real career here.”
As for himself? “I can't really imagine going out and looking for another job,” Adam says. “I want to see what we can build here. If someday we sell, go public, or the world just doesn't need us anymore — fine. But until then, I'm here.”