Kalee Hasselbach on building Plaid's culture

What excites you about your job?
My team focuses on creating platforms and opportunities for people to really connect and build relationships. Seeing them come to fruition is the most rewarding part.

What are some of the platforms and opportunities your team creates?
We plan our larger global events like Plaiderdays, which is a three-day long hackathon we hold twice per year, and our annual retreat. From a workplace design perspective, we're always focused on creating openness and pockets of social setups. We integrate casual, interactive spaces into the design of all of our offices so that people can come together to engage in meaningful conversations.

Why is investment in relationships important in a workplace?
At Plaid, we fundamentally believe that cross-functional relationships help us move quickly, do more impactful work, and think about things in a more well-rounded way.

Of all the internal events your team plans, which one is your favorite?
I think the retreat is really special because we're spending a week together out of the office. Last time I was there, I looked around and thought, I can't believe this is us now. I remember when it was, like, 25 of us, and we would pile into a few cars and drive up to Tahoe. Now, there's hundreds of us at our retreat laughing and having fun and getting to know each other. It's pretty surreal.

What is the biggest challenge you face in your role?
Staying ahead of how quickly we grow and how quickly things change, and staying dialed into how our workforce and internal culture is changing. Our principles help keep us grounded and guide how we function day to day, but culture is always in flux, and we want that process to be organic.

What are some of the anchoring principles that thread all of the Plaid offices together?
Outside of official company principles there are a few common traits that feel distinctly Plaid to me. Tenacity is consistent throughout all of our offices—so is our ability to make fun of ourselves. All of us are into having fun and being lighthearted and not taking ourselves too seriously. Support and growth is another common thread. The mindset here is, if you need help, I will jump in and help you. I'm here to support you. I would also say everybody is exceptionally hardworking and passionate. No one is just sitting on the sidelines watching the game. Everybody's in the mix. Everybody's hungry. Everybody's motivated.

How does your team stay ahead of culture change?
We have teams in every Plaid office, and we’re constantly doing pulse checks to make sure that we're dialed into Plaid culture and understanding how each office is growing and evolving. We're always asking how people think and feel about the company. Of course, we have more formal and official ways to collect those data points. But I think that the human aspect of checking in with employees and asking what they're excited about and frustrated with is special. We take all of that information into consideration when we make workplace decisions, so that culture never feels like a mandate.

What was it like being one of the earliest Plaid employees?
I knew it was going to be an adventure, and that's why I joined. In the beginning, nobody did just one thing; we were all so multifaceted. It was also a very raw experience. We saw the best and the worst in everyone, but it was extremely uniting because we were all going through it together. We put a lot of trust in each other. It was never a question of have you done this before? It was, how quickly and how well can you get this done?

How has your role evolved over the past five years?
I was originally hired as Zach and William’s [Plaid’s founders] executive assistant. I had never been an EA before, and they had never had an EA before; they didn't know what they needed from me and I didn't know what I should do for them. So, my role ended up focusing on special projects–specifically, figuring out how to build a world-class team.

From there, I transitioned to Recruiting and focused on building a lot of our early recruiting processes. But I retained this sub-component of special projects that I would tackle with Zach and William, and workplace projects started gaining prominence. Eventually, it became my single focus: figuring out how to retain the best team and make sure that working at Plaid is the highlight of everyone’s career.

You have had quite a few roles at Plaid! Why do you think the Workplace team felt like the best match?
Workplace’s mission is to ensure employees feel connected to Plaid’s mission, their work, and other Plaids by creating exceptional spaces, events, and programs. I have always been fascinated by the idea that changes in environment and experiences can impact outcomes, behavior, and sentiment in employees. Workplace is an industry where you get to flex a lot of creative muscle, both in how you approach solving problems but also in a very literal design and production sense. I am most fulfilled when I can get into a room with my team, and we develop truly unique and memorable experiences for employees that impact how they think and feel about Plaid.

What role did your family play in shaping who you are today?
There are two areas that come to mind when I think about how my family influenced me in my professional life. First, I learned at an early age that passion and purpose are requirements for defining real career success. My parents have always been deeply compelled by their work, and even as a child, I could tell they felt fulfilled by what they were doing day to day. Through them, I learned that it is really challenging to excel at anything that you are not intrinsically motivated to do. It’s important to give yourself the freedom to explore different things that you are drawn to and then figure out how to align that with what  you are really great at.

The second thing that comes to mind is fortitude. I was raised with the belief that great things do not come easy, and you should always be prepared to work hard and sacrifice in the pursuit of greatness and excellence. Building and growing at Plaid has never been easy, but I knew early on that it would be a defining challenge worth fighting for.

You also travel a lot between Plaid offices for work. How do you make the back and forth less stressful?
I refuse to check luggage, regardless of the length of a trip, which means I've become something of an expert packer. I roll all of my clothing, and I buy all of my favorite skincare products in travel size. I make a conscious effort to pack lightly and am constantly looking for ways to get out of the airport as quickly as possible. I also make a point to spend time with great people and do fun things when I travel. For example, Montauk has become one of my favorite places, so whenever I am in New York for work, I will make a trip out there to spend time on the beach with some of my favorite people.

What keeps you busy outside of work?
I spend a lot of time reading (mostly non-work related material) and always paperback. I love the experience of going to a bookstore and spending time picking out a few new books to dig into. I also love to explore the outdoors in San Francisco, because it feels like home. I grew up in Vancouver, so having the ocean close by comforts me, and being in nature and getting away from the business of the city brings me a lot of perspective and peace.

What are you proud of?
Hands down, my team. My biggest source of pride is seeing the people around me take on new things, execute flawlessly, and get really, really good at what they're doing. I have a special relationship with each person on my team, and I get something really different and unique from each individual. They are all so great about holding me accountable, challenging me, and pushing me to continue to grow and learn. Most days, it feels a lot more like a family than a team.

What are you looking forward to?
I get excited about new chapters and profound growth, and I feel like we’re experiencing that right now at Plaid with this Visa acquisition. I’m excited about what that means for the future and what we're going to be able to do as a company.

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