A former investment banker, Jaclyn Chen understood that an employee’s benefits are often underutilized, largely because employees find them a headache to navigate. Her company, Benepass, develops benefits management software so administrators can deliver employees access to everything from meals to mental wellness on an easy-to-use platform. It also centralizes all employee tax-advantaged accounts with a mobile app that employees can use to request reimbursements while including links to physical and virtual payment cards.
Benepass is helping companies reimagine how they manage and distribute benefits — no small consideration in an era when the competition for skilled employees is white-hot.
Q: Start with your background. Where did you grow up?
I’m the only child of Chinese immigrants. My parents came to the US in the early nineties — the classic immigrant story of people looking for a better future. We came to the US when I was four years old. We first lived in Richmond, Virginia, and then my mom’s job took us to Indiana. I grew up in Indiana in a town called Carmel, a suburb of Indianapolis, which is where I spent the bulk of my childhood, from first grade to my high school graduation.
Q: Did many Asian-Americans live in Carmel back then?
We were in the minority, but it wasn’t a zero situation because there was a big pharmaceutical company, Eli Lilly, that attracted a diverse talent pool to the region, including a decent number of Asian people. My high school wasn’t particularly diverse, but I wasn’t the only Chinese person by any stretch.
Q: Your folks uprooted themselves and relocated to the other side of the Pacific. Not easy.
It wasn’t. Like a lot of immigrants, their education and the degrees they received over there were not equivalent to what they could get over here. For example, my dad went to a university in Beijing where he worked as an attorney. But as you can imagine, a law degree from China wasn’t worth very much here in the US.
Q: How did they get by?
My dad did a lot of odd jobs, working in restaurants, selling furniture, and working at a FedEx warehouse. And then he went to law school at night. My mom had been a medical doctor in China. But she wasn’t credentialed to be a physician in the US, so she worked as a lab researcher.
Q: How do you think their example rubbed off on you?
I wanted to be successful because I knew that my parents had invested a lot in me. As an only child, that drive, or ambition, became ingrained in me. Certainly, my parents played a role early on in instilling the importance of education. And frankly, that’s how we were able to come to the US — because they had advanced degrees that allowed them to get visas to come work here. So, there was always this idea of learning since they wanted me to have a career that would offer me a degree of stability.
Q: As a young girl, what did you think you might want to do later in life?
Well, my mom wanted me to be a doctor. My dad was more on the liberal arts, law side and wanted me to go in that direction. But they recognized that I would figure out my own strengths if I worked hard. I always liked math and numbers, and I gravitated toward that. Also, I quite enjoyed writing — I was editor of my high school newspaper and thought about pursuing a career in that potentially, though it’s not always the most, um, stable profession.
Writing has served me well in a way that I perhaps didn’t expect it to. Because our company works remotely and I don’t get to see everyone in the office, I communicate with my team through writing most often. We’ve instilled a writing-heavy culture at Benepass. Especially as we’re adding new people all the time, the library of documentation gives them something to get up to speed on quickly.
Q: Apropos, you posted something on your LinkedIn page marking International Women’s Day where you talked about your ambition to become a chief executive officer. You wrote something to the effect that you realized the fastest way to do that was by starting a company of your own.
That was more of a joke, but it’s also true.
Q: How early on did being a CEO become an ambition, and what do you think drove you?
In my family, I’m a third-generation college-educated woman. Besides my mom, my grandma was also a doctor who traveled the world. So, I had that example of females around me having their own careers. And that idea of work certainly became a part of my own identity. When I was little, I liked to be in charge — I remember that I liked to boss my friends around [laughing]. I was always the organized one. In high school, I knew that one day I was going to do things. I don’t think I knew what that would manifest itself to be, but I was motivated, and it evolved into something deeper around being in control of my own destiny and putting my vision out there into the world and not being shy about that.
Q: I spoke recently with another entrepreneur who told me she realized at a relatively young age that she was a natural leader. Did you have that same feeling, or was that something that you grew into?
I think so. I was the editor of my middle school newspaper, and within my circle of friends, I was able to get people to do stuff by being in charge and being the most organized. Whether or not I knew when I was 12 that meant one day being a CEO — I don’t think I knew that quite so clearly. But I’m sure there are threads of that in my personality that developed when I was growing up.
Q: You spent your first years out of college working in investment banking. Was it a passion or just a way to learn a bit about the business world, cash a few paychecks, and figure out things until you were ready to start a company?
Yes. I started out in finance, which was a great training ground, and I really enjoyed my experience primarily because of the people I worked with. All the stereotypes about investment banking you hear were true. As a first-year person out of college, you worked 70 to 80 hours a week. You become good at the job just by the sheer weight of working twice the number of hours that is considered normal. I was surrounded by so many smart people, and I think that was the thing I appreciated the most, regardless of the actual work that we wound up doing. Everyone was smart, motivated, and thoughtful, and I was able to learn a lot.
Q: When did you decide that investment banking wasn’t for you?
Eventually, I got burnt out from working what were really long hours. Every year at investment banks, hundreds of new analysts start, and you feel like a cog in a machine, where the next year, there’s going to be someone else who’s in this seat. The finance firms now realize the turnover in their junior talent, but when I was there, it was very much a “two or three years and you’re out” approach because that’s probably how long you could hang on to that lifestyle.
Q: At what point did you realize, “OK, time to do my own thing?”
I had been working in finance/investment banking for about five years, and I decided to go to business school. When I went to Stanford University, I went in thinking that I could go back to finance, but I wasn’t sure. I was planning to treat business school as a two-year reset opportunity. When I worked in finance, I had the great fortune to work with senior leadership from a very early age, where I also would get to meet founders and CEOs of big companies. I always found those interactions to be the most interesting. So, at Stanford, I began thinking about coming up with something of my own or trying to work at a startup and seeing what that was like.
Q: How did you decide there was an opportunity to do something to improve how companies delivered employee benefits?
The idea came from being a corporate employee myself, working on Wall Street, where people are highly compensated in a benefits-rich industry. The experience for employees is quite poor. I had no idea what benefits I had access to. The companies I’d worked for had intranet pages listing a lot of perks and deals and discounts. You could sign up for this thing or that thing. But frankly, I was too busy and didn’t have the wherewithal to take advantage of all of them because it was such a disjointed process. It’s hard for companies to know that level of personalization and how to serve anyone at any point in time because it changes for that individual. When you extrapolate that across thousands of people, it’s basically impossible for a company to keep up with all of that.
Q: But this is after, what — decades of history? Isn’t that the way that benefits are traditionally implemented?
Right. It’s a one-size-fits-most approach, and it ends up being one size fits 5 percent.
Q: Why can’t the benefits system be more flexible?
It’s both cultural and a question of logistics. From a cultural standpoint, the competition for talent has been hypercompetitive in the last five to 10 years. Part of that is due to the Great Resignation. With most companies adopting hybrid or remote-friendly models, you can work for far more companies than ever before. That makes the talent market way more competitive because employees — especially the high-performing ones — have lots of options.
Companies that used to give out free lunch in the office — that doesn’t work anymore because not everyone’s coming into the office. And as your employees are scattering to all the corners of the world, it becomes harder to provide an equitable experience. So, logistics are forcing companies to think about all of this. That’s led a lot of corporations to focus on their values and how that gets expressed in their benefits and how they take care of their people.
Q: How do you think the “Great Resignation” is going to force changes in the business world when it comes to benefits?
If you are looking to hire and grow your team and are concerned with hiring the best talent, you absolutely need to have more flexibility across a lot of different dimensions and certainly in benefits. The employee experience must be at the forefront, and flexibility is the keyword. You can’t have people feeling as if they’re second-class citizens because they’re not physically going into the office.
When companies get asked to describe how they pitch employees to come and work for them, they need to think about that as opposed to, “Oh, here’s our great job. I’ll just post a salary and some basic benefits, and they’ll come to us.” I think it’s totally shifted the other way.
Q: I read a piece you wrote where the bio refers to Benepass as a leading fringe benefits administrator dedicated to making benefits flexible and delightful for companies and their employees. Maybe it was my own experience working for some very big companies, but when it came to benefits, there were many adjectives I might have used to describe them. The term “delightful” was not among the choices I would have selected.
And it’s such a shame because the company is actively spending and making an investment in you as an individual, trying to take care of you in some sort of way. Unfortunately, the complexity and the annoyances and the administration get in the way, and that leaves the employee wondering why this is so hard. But that’s given us a great opportunity to dramatically simplify the experience: companies taking care of their employees and having employees feel happy about that.
Q: I’d like to shift back to what it was like when you were starting out. You were approaching potential clients with a very different way of doing things. What challenges did that present?
Going from zero to one (client) is difficult. You must get used to people saying no and thinking it’s not a good idea. You have a vision for something different, and you must be persistent around that. That was probably the most difficult thing for me personally. I had nothing, maybe negative momentum, and that was hard to overcome. Early on, my vision wasn’t as fully fleshed out and, of course, it’s still evolving. In fact, I remember once talking to an HR leader who basically said that my presentation deck looked like a school project. She wasn’t wrong.
There was a high degree of skepticism that I needed to overcome. Once I began to secure customers and word-of-mouth referrals, there was a groundswell of momentum to build on. But in the early days, it’s hard to gain momentum for something when you’re starting from nothing.
Q: So, this was the culmination of a dream, but how ready were you for the role? Did you have to learn on the job?
My job changes dramatically every six months. As a founder, the job, in the beginning, is to talk to as many customers as possible and be super scrappy and do whatever it takes. You network like crazy and you’re pitching your idea all the time. I was also learning to sell. Previously, I had worked as a financial analyst who used an Excel model to come up with smart-sounding business themes, takeaways, and trends. But I’d never actually sold anything in my life. So, what you rapidly find is that your idea and you as a person become kind of interchangeable. You’re essentially selling yourself and that was very foreign to me. And then you’re also speaking with investors, and that’s a different ballgame entirely where you’re talking about things such as the size of the market and your business model. At least I had some more experience on that front given my background.
Also, we were four people on a WhatsApp chat not that long ago. Now we’re a team of 30 people and I’m effectively hiring for things that I’m not that good at — sales, marketing, operations, product, and engineering. None of those are my core skill sets, so you need to learn how to manage people and become a leader. That’s been another evolution.
Q: That’s obviously a lot. Is it what you expected?
I think it’s everything I signed up for. And in terms of the learning experience, it’s completely unparalleled to any other job that I could ever have. It’s been challenging. I don’t like being bad at things, and I want to be successful, and I’m driven by that. So, when you change what your job description is dramatically every six months, you’re going to make mistakes along the way, and I must be patient with myself — which is not my forte. But I accept that I will get better at this over time, or I will find someone who’s better at it than me and work with them on it.
Q: It sounds like a huge part of the entrepreneurial learning experience essentially comes from trial and error.
A lot of it is. And I think what I’m also learning to accept is that in the early phases of my career if I was not good at something, I would desperately try to be better at it. And I think where I am now, especially as a CEO, is that’s not a scalable mindset. So, I have to accept that here are the things I’m good at, here are the things that give me energy, here are the things I want to do — and here are the things that only I, as the CEO, can do. I need to focus on that narrow subset and everything else I have to accept and give away.
Q: What’s been the most rewarding part of being where you are?
Hearing from our end-users, the employees who use our product, about how the benefits that they’ve been given access to as a result of Benepass have helped them to do something they normally couldn’t do for themselves. All those different use cases are just heartwarming. The other thing I would point to is the team that we’ve built. I’m proud of not just the product and the service that we’re building but also the company that we’re all building together. It’s a joyful group of people and a great environment to work in. I can’t imagine doing anything else where I’d be learning more than what I am today. And I love that I can set the tone for the culture and work with incredible people who have hopped on this journey with me.
Q: Considering what you’ve learned, how would you counsel an aspiring young entrepreneur before they start down this path?
I hear from a lot of people things like, “Oh, I’m interested in doing it, but I don’t have a great idea.” I think ideas are great. And obviously, certain ideas are better than others, but there’s so much in the execution. Your idea will change so much over time. It will be refined. It’ll be totally different. But the flip side is that it’s an intense journey in a way that I don’t think I could have predicted going into it, regardless of what people told me. I thought I had worked hard and been proud of my work in my previous life. There’s a certain amount of grit and persistence that I don’t even think I had before, but now that I’m doing it, you have to find it within yourself. And it is really, really hard.
Q: What do you do to blow off the stress? Do you have hobbies?
I don’t have a lot of time for hobbies. I work around the clock Monday through Friday afternoon and try to shut off on weekends and not work or answer emails. I obviously look at emails and Slack, but our company really shuts down on weekends. And I try to set the tone for that as well. I need an extended period where I don’t have to think about work, I think that makes me fresher, and so that’s something I try to maintain.
Q: Good for you. That brings us to our three last questions. What’s your favorite book?
“Give and Take” by Adam Grant. It’s about interacting with other people and being a giver and being generous as a mindset.
Q: What’s your favorite movie?
“Love Actually.” I watch it every Christmas.
Q: Finally, who is the one person who’s had the most professional impact on your subsequent career as a businessperson?
My mom. Just her setting an example of how to balance work and family and how to be intrinsically motivated by the work that you do and want to be good at it. And how that doesn’t take away from your ability to be a good mom or a good wife. That was very much ingrained in me from an early age.