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Advice / Succeeding at Work / Getting Ahead

How Expensify Helped This Software Engineer Grow Into an Invaluable Generalist

Robert Chen, an engineer at Expensify

There’s never a boring day at Expensify, an expense management platform that’s used by more than 8 million people around the world. Just take it from Robert J. Chen, a software engineer who joined the company in 2012, first in the San Francisco office and now working remotely from Taipei, Taiwan. “No two days are the same here, and that’s part of the reason I’ve stayed for what could be considered a lifetime in the tech industry,” he says. “It’s unbelievable to witness the company grow from a small, scrappy startup with a score of employees into a global juggernaut. And I still feel like we’re just getting started.”

Here, Chen shares how he’s encouraged to evolve as an engineer at Expensify, why anyone can be a leader at the company, and what it was like to prep the product for a Super Bowl ad.


Tell us about your background and how you came to work at Expensify.

Coming out of college as a computer science major, I thought I had a background that most employers would find interesting. As an intern, I worked on engineering projects at NASA’s Jet Propulsion Laboratory, the Scripps Institute of Oceanography, and Fermilab via my school’s physics department. I spent summers abroad in Asia and Europe working on a diverse set of engineering problems. I built an image-processing program for marine biology research, real-time data visualizations for airborne weather radar, and bioinformatics apps for a supercomputing center.

After going through numerous interviews post-graduation, I found that most companies had no idea what to make of my background. From a business perspective, they were simply looking for a candidate with a basic but specific set of marketable skills, all to meet the criteria on a checklist. It seemed like they had neither the patience nor the resources for a candidate who was a jack-of-all-trades. And while some larger, traditional companies were more willing to take a chance on me, the trade-off was that I would end up on a rigid, one-size-fits-all track, severely undervaluing my diverse experience and skills.

This all changed when I was introduced to Expensify. The word “generalist” on the job description stood out to me because it perfectly described my background—and the fact that it was mentioned at all proved to me this type of talent was valuable to them. They were looking for someone who wasn’t afraid to wear different hats and was flexible enough to study and engage with any sort of problem, especially if it was outside their comfort zone. Here, I could draw upon my broad experiences to tackle unique challenges. I found a home.

What has kept you at Expensify for more than seven years?

I’ve stayed because of the new experiences that come up daily that keep me challenged and motivated, as well as the unmatched flexibility to travel the globe while working full time. Not only is seeing the world encouraged, it’s actually expected with opportunities like Offshore, when the entire company relocates to a different destination for a month every year. But the adventures don’t end there. There are always new opportunities that come up internally, and anyone is free to raise their hand if they want to take on a project.

How have your responsibilities evolved during your time at Expensify?

I started out by building functionality on Expensify’s website, for both the front end and back end. I switched over to mobile app development for Android and iOS, followed by work on accounting software integrations, banking integrations, and much more. Throughout this time, my responsibilities have also included pushing out new versions of Expensify to the App Store, attending cloud-accounting conferences, and meeting customers and partners. The evolution I see in my responsibilities is simply the expansion of various activities beyond what a traditional software engineer is expected to do. At Expensify, it really comes down to my personal selection of the experiences I want to have, the challenges I want to take on, and the projects that I choose to be responsible for.

How has the company helped you grow as a software engineer?

Expensify has an internal growth and recognition program that encourages engineers to expand their skill sets. One day you could be working on the mobile app and the next day you could be tweaking business SQL queries. There’s no end to the diverse range of technical challenges that you can volunteer to take on. Being able to own a feature from the front end on mobile and web to the back end in the database has helped me grow not only my technical skill set, but also my design chops.

How have you stayed productive while working remotely in Taiwan?

Expensify uses a variety of techniques to ensure that everyone is on the same page, whether they’re in the same office or 15 hours ahead, in my case. This includes posting quick summaries of major discussions on Slack at the end of a workday and being super-communicative during overlapping work hours. This ensures that nothing is left up to doubt and that the most important messages are getting across. We also coordinate on a shared document, a one-stop shop that tracks the company’s top priorities, the team members involved in the various projects, high-level updates, and items that require particular attention. Therefore, we can pass the torch on work items across time zones, ensuring continuous momentum and progress on projects.

Since switching from an office location in San Francisco to a remote environment in Taiwan, I’ve held more tightly than ever to Expensify’s two rules: Get Shit Done and Don’t Ruin It for Everyone Else. This mutual trust and respect ensure that we work together as a single unit, despite the geographical distance. These aspects have been effective in keeping me focused throughout the work week, providing full coverage to engineering duties, customers, and partners across the globe.

What’s the most exciting period of growth you’ve experienced during your time at Expensify?

I could name a bunch, but I'll give you the most recent example. The buildup to the launch of our 2019 Super Bowl commercial required a ton of planning and work across the company, from engineering to sales and marketing. We made sure that we had a product that was not only stable, but also presentable to 100 million people around the world. During this period, I learned that we were no longer just a small (but mighty!) tech startup. Instead, we were a cultural phenomenon capable of making waves on an international scale. It was a humbling experience, and certainly a highlight of my career at Expensify.

As Expensify has grown, what’s one thing that’s remained constant?

Everyone in the company is expected to interact with customers on a daily basis by handling support questions. This helps all teams stay up-to-date with the product and ensures we’re in tune with the daily experiences of our users.

What are you working on right now that excites or inspires you?

I’m currently working on partner banking integrations. It’s exciting to know that a few strategic lines of code or a small feature could unlock major business and partnership opportunities that benefit mutual customers. Also, working with external teams gives me a glimpse into how other organizations operate. I get to learn how they generate fresh ideas, incorporate new perspectives, and handle critical feedback from others. These eye-opening interactions make the engineering work I do feel far more rewarding and impactful.

How would you define leadership at Expensify?

Expensify is a flat organization with no official titles outside of each team’s core function: engineering, marketing, business development, sales, success. As such, leadership is fluid, meaning anyone can be a leader and a team member at the same time. There are two main steps to leadership at Expensify. First, take the initiative to identify a problem, come up with a solution, and draft a plan to accomplish your vision. Second, more crucially: rally, enable, and inspire others to work toward your vision by clearly communicating its potential value and impact to the rest of the team. Initiatives can range in size and complexity from releasing a small feature on the mobile app to rolling out a full-scale product extension like the Expensify Card. All in all, what’s left is an even playing field where everyone has an equal chance to propose ideas, and proposals survive on their merits alone.

What advice would you give someone applying for a job at Expensify?

We don’t ask for resumes, though they might help provide additional context. The best advice I can give is this: Take your time on the questions, tell us your story, be genuine, share your dreams and aspirations, and let your personality shine through. At the end of the day, we’re not looking for someone who checks a certain set of boxes. We’re looking for someone who constantly questions the status quo, assumes the best of everyone, and enjoys solving “impossible” problems. We’re looking for a talented, ambitious, and humble human who we can invest in and grow with.