Katie wasn’t looking for a new job. This is how Kit’s empathetic interview process and founder-led vision convinced her the risk of starting over was worth it.
This article is part of the Life at Kit series to help job seekers learn more about the team and gain a deeper insight into the behind-the-scenes of what it’s like to work at Kit.
Katie didn’t always know she’d work in tech one day. All she knew about what she wanted to be when she grew up is that she never wanted to do “just one thing.”
I was always a generalist growing up. I loved business, art, technology, and communication. I was always curious about more, and I really hated being defined by one thing.
She came to work in product by way of a business development role at a tech company. In that role, she was always talking to the engineers, asking questions like “Can you do this? Can you add a button here?”
Finally they were like, you’ve asked us so many questions about this; why don’t you take on the role of product?
The more Katie learned about working in product, the more it seemed perfect for her.
I loved the idea of creating something from nothing; people have a problem, and you get to make something that solves a problem for them.
And to do that, you get to orchestrate these amazingly skilled people to get the best out of what each of them are really good at. It wasn’t just one thing. That was how I fell in love with it.
Katie excelled at working in product at a few tech companies. She loved her job, her team, and the products she was building; she wasn’t looking for a new job. But then, a recruiter reached out.
“Instead of it feeling like a trick.”
While running Square’s e-commerce product team, Katie received an email from an executive recruiter for Kit’s open VP of Product role.
She was happy and wasn’t looking to leave, but she was intrigued by the email, especially because of the idea of working directly for a founder, and for a bootstrapped company.
I was really interested in running a product team at a company that was bootstrapped. I’d worked at VC-backed companies and public companies, but never for a private company that was self-funded.
The idea of building a product in a sustainable way that doesn’t have outside pressure from investors that need to see an exit in 18 months was really exciting. And that paired with working for a CEO who had a vision and a lot of real empathy for the customers he was building for? As a product leader, that’s everything you want.
Katie applied and made it to the interview stage. But she was nervous, and a bit stressed. She’d been working long stints at her past companies and had been directly recruited by an old boss, so she hadn’t actually done a formal interview process in 14 years.
And her first interview was going to be with the founder and CEO of Kit, Nathan Barry. But before that interview, Nathan sent Katie a 10-minute Loom recording to give her context on the product and what they were looking for.
I was so impressed that there was so much preparation put in. That gave me so much confidence to have a better conversation and know how I can help and how to share what I’ve done.
And the rest of the interview process was so lovely too, with the questions given in advance. Having not interviewed in a really long time, being able to think through how I can share something that would be valuable in the interview ahead of time was really helpful, instead of it feeling like a trick.
“Am I going to give that up to go take a chance?”
Katie loved the interview process, but she was still nervous to move forward and leave a job she loved.
I think change is so hard. I had an amazing team at Square and to me, your job is such a large part of your life. I see the people I work with more than I see my kids during the week, which is crazy. So I think change is really difficult.
While I knew I was ready for a different challenge and a new environment to pressure-test my skills and help me grow a little bit more, I also really love my comfort zone sometimes.
You have your people and your processes and you feel smart and trusted and you’re like, am I going to give that up to go take a chance and rebuild the trust somewhere new?
But she ultimately decided to take the job. She says what helped her move past her initial anxiety was the people she met at Kit.
Nathan [the founder and CEO] and Dave [the Chief Revenue Officer] were the two people on the exec team I talked to the most, and I just got very energized talking to them.
I was like, I wanna work with these people. They seemed kind, they seemed humble. And they had families and interests outside of work, which for me as a woman in tech with a family was actually really important.
I wanted to see people who were real. People who weren’t just like, “This is my job and I come to work and everything is about work a hundred percent of the time.”
I felt like the risk was worth taking for the opportunity to build something really cool, grow my skills, and push myself out of my comfort zone. But it felt easier to do with a group of really kind and smart people around me.
Katie joined Kit as the VP of Product in 2024. And then everything changed.
“People who aren’t a hundred percent defined by having a tech job.”
Katie joined Kit during a time when AI was beginning to change almost everything about tech.
I try to think about it as if you’re 70 years old and you look back and you were running a product company in the middle of this major technology shift; that makes it a lot less scary and a lot more interesting.
What I’ve noticed from interviewing people is that some of their proudest professional accomplishments happen in those moments—not when everything is super stable but when the ground is shifting and everyone is kind of freaking out.
That’s where you get to shine and showcase how you think differently, how you want to show up, and how you want to be human in a moment that maybe feels less human in this case.
While at Square, Katie was part of running a program to encourage teams across the company to explore generative AI and helped launch 32 new AI features across the company.
At Katie’s first Kit team retreat, when AI was still relatively new (and a little scary), she presented a session called “Katie’s hot takes on AI” to start the conversation and ignite curiosity. Since then she’s been a leader in shaping the company’s AI strategy, inspiring many others to embrace and experiment with AI tools while also imbuing them with confidence in the unique value they provide that can never be replaced.
Because to Katie, it’s the people that make her job worth doing.
The thing I love about Kit is that the people who work here are so creative and such full people.
Having come from Silicon Valley tech, it’s typically more like you work in tech and that is your life; it’s easy to get caught up in that cycle.
But everyone on the Kit team are such interesting and whole people who aren’t a hundred percent defined by having a tech job, but still have that strong work ethic.
Katie says this also extends to the culture of the executive team.
I love working with all of them. It’s a very silly and fun culture but also highly productive.
There’s also a lot of empathy between us all. And there’s no “land grabbing,” where people are like “I want a bigger team.” That has been so nice here. They’re just like, “What do you need?” “How can we help each other?”
In her role now, Katie loves that she is able to operate at the intersections of product and people, design and engineering, and sales and service. And just 18 months after she started at Kit in her VP role, she was promoted to Kit’s Chief Product Officer.
But it’s the vision that keeps her excited to wake up every morning.
This morning I jumped into a design review meeting for a vision of a product we’ll start building next year, and that is literally the most fun thing in the world to me: seeing really smart people we’ve hired truly understand the problems we’re solving, and innovating in a way that’s going to make our creators so happy.
That’s why I say I like meetings. Because for me, if that’s the work, it doesn’t feel like work.
Want to be a part of a driven, creative, and fully remote team that focuses on serving creators? Check out our careers page.
