This blog series is dedicated to celebrating our Black, Latinx, and Women Engineers who are making an impact in the lives of our Gusties and Gustomers (Gusto customers) every day.

Today, we're spotlighting Upeka Bee, who has been with Gusto for 5 and a half years. She is currently the Head of Engineering for the PIE group (People Information Ecosystem). She joined Gusto as a Staff+ in the Payroll group, after which she moved into engineering leadership and has led many different teams and groups during her long tenure.

Our interviewers are Abby Walder and Kim Nguyen. Abby works on Gusto’s Invite Team to hire software engineering talent, while Kim builds features to improve the partner developer experience as part of Gusto Embedded.

Upeka posing in front of a mural

Abby: How did you join Gusto?

Upeka: My first job out of grad school was at Salesforce, back when it was still in its early hyper-growth phase. I was very lucky to get a front row seat to their fast-paced growth and the very real growing pains that came along with that. And after I was there for 7 years, I had an existential crisis – “what do I do now?”. I felt a calling to apply those learnings at an earlier stage company.

My next role was as the founding engineer for a 4-person startup. We were a small group of people who worked very hard, trying to build a product that could solve problems for our customers.

The startup eventually failed, but the most important things I learned were: 1) product-market fit is the most important thing - i.e., solving the most important problems for your customers, and 2) teams need collaboration between product, design, data AND engineering to build products that are delightful and easy-to-use. The next company I was going to work for had to have both of these.

And that’s when I came to learn about Gusto - I kept hearing their customers rave about it! Once, I was in a Lyft Line (remember those from before the pandemic?) and mentioned to the person in the car that I was thinking of joining Gusto - and they said “Oh I know Gusto, I get paid through them. I LOVE Gusto! I love their email (referring to our payday email)”.

I was taken aback - I would never have pegged “payroll” as a super exciting product space. But the more I started to learn about it, I realized that Gusto was solving real problems for business owners. Gusto helped business owners to run their businesses and take care of their people - i.e., help them get paid, give them benefits, help them stay motivated and inspired.

And on the surface these problems that Gusto was trying to solve didn’t seem that complex. Except the more that I learnt, I realized that paying people and dealing with taxes and health benefits coupled with the differences in each state - all meant that this was a very complex space.

And finally, the impact on real people running businesses, people needing to get paid so they can take care of their families coupled with the challenge of the complexity, made Gusto my top choice.

Abby: In your role here at Gusto, what has been one of your proudest accomplishments/impacts you have had on the SMB customers we serve?

Upeka: What I’m most proud of is continuously improving the experience for customers. In the almost 6 years that I’ve been at Gusto, we have - maybe quadrupled - the number of customers we’ve served. The software we’ve built is a “must-have” for our customers. Business owners need our services so that they can take care of their people. And those people in turn need Gusto to be accurate and reliable so that they can take care of their families.

So being able to continue improving the quality of our products while expanding the number of people we serve has felt incredibly meaningful.

Abby: How has Gusto played a role and supported you in your journey as an engineer?

Upeka: One of my favorite things about Gusto is that its inclusive culture and growth has afforded me many opportunities to learn and grow in my career.

A while ago, I told my manager off-handedly that I wanted to try my hand at engineering management. It was something that I have been curious about for a while (see previous reflections on the topic here).

My manager listened to that, carved out an area of ownership and offered me a chance to pursue it. More importantly though, they made sure I could fail safely. This was critical because it gave me the opportunity to learn and while ensuring that we were still able to continue to meet our customers’ needs while doing so.

It ended up being a pivotal moment for me because it helped me realize how much I loved helping people grow and leading teams.

Abby: What advice would you give to someone looking to break into engineering or are just getting started?

Upeka: I suggest trying to get to know people in the industry. There are so many online resources and groups nowadays. It’s so endearing to me when people reach out randomly, like “hey, can I talk to you?” I love taking those calls and sharing what I know.

Upeka loves thrift shopping

Kim: What does your typical day at Gusto look like? What are your favorite parts of the day?

Upeka: In my current role as Head of Engineering for PIE, I empower a group of teams and their managers. I also partner with my Product, Design and Data counterparts to create strategy and vision for our group. The vision of PIE is to ensure that more people get to eat more pie. Just kidding - we like to make jokes about baked goods. :)

PIE stands for People Information Ecosystem and our vision is to make Gusto into a people platform / HRIS, that helps our customers take care of their people through HR features such as performance management, applicant tracking, learning and development, insights and reporting etc.

At a high level we are focused on solving problems for our customers, in the features that we own. We have a lot of ways to understand their pain points and feedback - we do customer interviews, we get feedback through the app, we listen to customer calls, measure and instrument our product - and then review all this carefully. All this insight goes into updating our roadmap - we try to be as agile as possible, iterating on this feedback and modifying our plans quickly. Again the cross-functional collaboration between engineering, product and design is critical and it helps us to build a product that is delightful and opinionated when performing complex tasks.

A typical day can look different from day-to-day, and typically the first thing in the morning is our leads-sync meeting because my product and data science partners are based in the New York office. In those meetings, we align on any important customer issues that have come up, the team's strategy and roadmap for the next 1-3 months. Lead syncs are some of my favorite because it’s a very safe space and we are able to debate complex topics openly. We’ve built a lot of trust and we can be real about what’s not working while still joking around and having fun.

Every other week, we have a “Show and Tell” where our engineers, PMs and designers show early demos of what they’ve been working on - and help us understand what customer problems it’s intended to solve. It’s a fun experience with lots of laughter, kudos, exciting demos and discussing the impact of what they are building. We try to celebrate learning and experiments along with the wins because we build a lot of 0-to-1 products and experimentation is very important for that.

Another big part of my role is helping the many teams in our group understand our vision, roadmap and strategy, or any changes to them. And in the afternoons, I carve out maker time, one to three hours. I spend this time brainstorming about various problems - this might be customer pain points, team problems or changes etc. And then I spend the time writing documents on these ideas or creating plans. I find that storytelling is important for these documents because it increases the engagement - so I spend time trying to make things funny or interesting, and this helps me flex my creativity and that’s a lot of fun too.

After that, I’ll typically have 1-on-1’s with people that I directly empower and skip-1-on-1’s once a month.

Kim: What's something that working at Gusto has taught you that you will continue to take with you in your career as you grow?

Upeka: Working at Gusto has taught me many things, especially about creating healthy and happy work environments and building products. Recently I’ve been thinking about how each team is like a three-legged stool. Each function that we have – Eng, Product, Design– is like one of the legs of the stool. If one of those legs doesn't work, then the team falls down. We won’t be able to make a product that our customers love if one of those functions is not working.

So if Engineering is thriving, that’s not the end of my job. I need to cross the boundary of our function and help my lead on the other side if they need help. At the end of the day, the team’s not going to be able to help customers if all our functions aren’t able to thrive. Most high-functioning teams have each function doing well. The more we can help each other, the more teams will be successful.

I wrote about iterative product development in Increment magazine, Planning in Dark.

Kim: How have you sponsored other engineers? Is sponsoring other engineers an important aspect of your role?

Upeka: As an engineering lead, sponsorship is a core piece of my job. Motivate, hire, and inspire – that’s my job. I start by understanding what motivates people. What are they interested in? What are they good at? Then I constantly look for opportunities to align those motivations and passions with business problems. That’s what I think helps keep people engaged.

Kim: What are some resources you've learned from? Any particular role models?

Upeka: Because I came into management late, I read a lot of stuff. So I read books and re-read books.

Mentorship has really been helpful and I have been lucky to have some really good ones. Mentorship is interesting because it’s a little bit like friendship. Sometimes there’s chemistry, and sometimes there isn’t, and that’s completely okay.

But the biggest thing that worked for me was for me to ask for mentorship, even if I didn’t know if they would mentor me. Sometimes they would end up saying “yeah sure, I’ll mentor you, let’s have a coffee chat.”

Upeka’s cat, Winston Purrhill

Kim: What advice would you give to a senior engineer on how to start operating at the Staff+ level here at Gusto?

Upeka: Going from senior to staff means that the technical things you build become more leveraged. Instead of an engineer writing code, and enabling a single feature, a staff engineer writes code, and then that enables many features. Your impact becomes more amplified.

It starts with an open and honest conversation with your manager on what you’re passionate about. What are the critical business areas for impact?

You also have to be honest about it - building an amazing technical thing that doesn’t have a lot of impact for your customers is insufficient. It could also mean that you have to switch teams, or work on a different problem. It means that you may have to change the systems around you to make it work for you. But it all starts with having an open conversation about the important business problems to solve - and your manager is a great person to have that conversation with.

If you’re interested, I wrote about The Care and Feeding of StaffPlus Engineers here.

Kim: Thank you so much for taking the time to talk to us!

Upeka: Oh yeah, totally! Thanks for talking with me.