Building the team at Flip is about finding people that raise the bar for the entire organization. But what does “raising the bar” actually look like here? We went straight to the people who live it every day.
Who Are We Looking For?
The short answer? Builders. But let’s get more specific than that.
Meghan Dwyer, our Lead Recruiter on what makes Flip’s team tick, puts it this way: the people who truly thrive here are obsessed with what they do – not in a buzzword way, but in the kind of way where they’re coding for fun on a Saturday, or thinking about a client’s problem long after they’ve closed their laptop. They’re their own toughest critics. And when they show up to the process, you can feel it.
“The ones where someone actually did the take home themselves – you can see their personality in the work,” Meghan says. “That quickly translates into someone on the team diving in and bringing their own perspective or approach to solve problems.”
Ava Winslow, Flip’s founding Healthcare Account Executive who’s been building our presence from the ground up, echoes this: “It’s definitely people who don’t need training wheels. People who can spot an opportunity and know when to take it and make it their own.”
Wendy Halson, Head of Customer Success, adds another dimension: the best candidates are curious and collaborative – people who are genuinely excited about solving problems that directly impact the client experience, not just checking boxes on a job description.
From the recruiting side, Matthew Grimaldi and Connor McDermott, Recruiting Coordinators, agree: the ideal candidate has something tangible to show for the work they’ve done before. Did you materially improve something at your last role? Did you identify a problem and actually fix it? That’s the kind of ownership mentality that gets everyone here excited.
The common thread across all of it: if ambiguity energizes you rather than slows you down, you’ll fit right in.
What’s It Actually Like to Work Here?
Joe Garlick, Lead Architect, explains that, “It’s just different here. You can see everyone’s invested. Everyone wants to make it work, and everyone’s excited to come to work every day.”
Flip operates on a simple but powerful principle – one that Ava says has stuck with her since her very first interview: tough on standards, easy on people.
“We have a high standard. We have a huge mission we’re working towards,” she says. “But the people are really the focus at the end of the day. And that’s something that never gets lost.”
Meghan describes it from a different angle – one rooted in autonomy and trust. “I am someone who thrives in high-ownership environments with the autonomy to build, pivot, iterate, and make decisions on my own. Rarely is someone going to tell you what to do, instead they will ask your perspective or ask for your collaboration. Each of us are responsible for getting sh*t done.”
That level of ownership is intentional. There’s a transparency shared across the business that gives everyone a window into what leadership is working toward, which means each person gets to be the domain expert in their own area, without someone looking over their shoulder.
Wendy describes it as a place defined by real ownership and partnership – where people genuinely care about the work, support each other, and are always pushing to make things better. “It’s not performative,” she says. “You feel it.”
For Matthew, joining Flip was a confirmation of everything he saw from the outside looking in: “What drew me in was the culture I saw coming through Flip’s LinkedIn, website, and YouTube. The most surprising part? The autonomy. It gives me the space to build, grow, and make my role my own in a way I’ve never experienced before.”
And Connor sums it up simply: “Not only do we work hard, but we collaborate and play just as hard.”
The Moments That Make It Worth It
Ask anyone on the Flip team about their favorite memories, and you’ll get answers that range from milestone-big to beautifully small.
Ava talks about her first road show: 12 states in two weeks with teammates she’d never met in person. “It’s like we had known each other for months and months,” she says. She also talks about returning to an industry conference a year after attending as a total newcomer: “It was almost like a hometown reunion. I recognized all the vendors. I had a group of familiar faces. It just felt like fun, like this is my circle.“
Then there are the niche, only-at-Flip moments: learning card tricks from a client at a conference in Chicago. Picking up a new hat in every city she and her colleague Jordan Dardenne travel to for work – and then having a client team in Chicago surprise them with Chicago hats on their last day, keeping the tradition alive without missing a beat.
Wendy keeps coming back to the travel: getting to visit clients in person with her teammates, exploring new cities together, and building the kind of shared memories that only happen when you’re out in the world doing real work side by side. “Our clients are a lot of fun,” she says, “and getting to connect and collaborate with them in person makes it all feel worth it.”
Meghan’s perspective gets at something deeper. Yes, there’s the Series A, the billboard, the late nights in the office, biking across the city with the founders. But what she keeps coming back to are the small things.
“The random Slack messages. The walks to get lunch. The Spotify jam sessions. When several of us are trying to work something out and you hear different POVs come to the table. It’s the things that remind you that you have good teammates, but also good people around you, who care about you and the work, and still show up.”
Eugene Bann, Head of AI, describes what makes his day, every day: “The very first thing I was looking for was a solid team to work with. To this day, that has remained a very high bar. Everyone I work with is phenomenal, and that is probably the number one reason why I love working at Flip.”
Okay, I’m Sold. What’s Next?
If this sounds like the environment where you do your best work, we’d love to meet you. Flip is hiring across multiple departments, check out our careers page for more info.
