Meet Our Operations Team: Q&A With Dan Ross, Head of Strategy and Operations

Our mission is to reimagine how companies take care of their people. At Benepass, the Operations team works directly with our customers to understand their challenges and implement modern benefits programs that meet their employees’ needs. 

Get to know our Operations team in this Q&A with Dan Ross, Head of Strategy and Operations at Benepass.

How did you end up at Benepass and what made you join Benepass?

I was looking for two things: (1) a deep need in a market with big potential and (2) a great founding team.

(1) Benefits are a huge market and a huge part of our compensation for working, but they’re so broken after decades of neglect. To only slightly exaggerate, no one has meaningfully innovated in the benefits space since WWII. Companies do a step challenge (2000s) or buy their employees Headspace subscriptions (today) and think they’re innovating. Employees mostly tune out everything beyond health care.

There is a huge opportunity to change people's relationships with their employers by remunerating people better with more thoughtful compensation and benefits. Benepass is extremely well positioned to lead this change.

(2) Benepass is my third time through an early-stage startup. Building a company at any stage is really hard work — but hard things are often the most rewarding. In choosing a team, I wanted to find a group of people that really cared about their work, cared about each other, and were just generally great people to put in hours with.

Virtually all CEOs are super sharp, decisive, and thoughtful. Benepass’s CEO, Jaclyn Chen, is all of these things. She’s also kind and a great human, and she’s built a team of of like-minded, good people that are fun to work with day in and day out.

Tell us a little bit about the Operations department. Why would someone want to join your team?

The Operations team is where the rubber meets the road. We’re responsible for delivering on Benepass’s lofty vision day in and day out with our clients. Sometimes that means spinning up processes to get something done that we know we’ll build product for in the future. Sometimes that means just really listening to a client to uncover their spoken and unspoken needs and make sure we’re delighting them.

We have a dual mandate as a team, which is to both execute on behalf of our clients today and to build better process and product so we can scale what we’re doing to hundreds and thousands of clients tomorrow.

What qualities do you look for when hiring someone for the Operations team?

People that succeed on the Operations team are looking for hard problems and growth. This is gritty, often unglamorous work, but it’s also work that is highly autonomous. We have tremendous flexibility in how we solve hard problems, and we let people on the team figure out the best answer to really important questions facing Benepass today.

It depends on the role, of course, but in general good fits for our Operations team are people who are highly process-oriented, care deeply about customers, and are able to roll up their sleeves to grind out something important but detail-oriented and in the same moment take a step back and ask why we’re approaching a problem the way we are to propose alternatives and better paths forward.

What is your favorite core value? How does the Operations team display it in their daily work?

Bias toward action, which means sharing work at 50% and optimizing reversible decisions for speed. 90% of decisions are reversible.

We’re a team that has to get it done for our clients day in and day out. There’s no way to succeed as an Operations team without a bias toward action. The reason I like this principle so much, though, is the idea of sharing work at 50%. 

It’s easy to make decisions quickly, but it’s hard to make great decisions quickly or to build great project plans quickly. I like this principle for the calibration required — in both directions — between sharing in the very early days and when something is fully finished.

It’s much better to share work early than to wait until you have a fully finished product to present. This reduces the pressure to have something perfect before sharing, which lets us move faster individually and as a team. But the principle is also not “share work at 10%.” It’s valuable to put in the early work to give your team something to react to and build from.

What exciting things are in store for the Operations team as Benepass continues to grow?

Part of what makes operations fun is that there are always new and unexpected challenges at each stage of scale. Sometimes there are challenges we know are coming, that we can plan and build for, and sometimes the business just evolves quickly when we sell a new customer or release a new product and need to all of a sudden support an entirely different type of product, business, or workflow than we expected. I’m excited for the unexpected new challenges just as much as the ones I know are coming.

Among the things we already know are critical as we grow are building more and more muscle around getting ahead of our customers and solving problems at their root. Our Customer Experience team has a principle of figuring out the “question behind the question” and tailoring our answers to the underlying questions, not just what we’re asked at a surface level. More broadly, as a customer-facing team, I think we’re unusually good for our stage at working to get ahead of customer questions and issues through education.

There’s an opportunity to keep building ahead of our customers across the Operations team. For our Customer Experience team, this looks like evolving from great help center articles and videos toward best-in-class, proactive user education delivered across all of our platforms. Similarly, for our Customer Success team, we’re just at the early stages of building experiences for the HR teams we work with that ensure success at each stage of the customer lifecycle and proactively guide clients toward success as they build their benefits with us.

Interested in joining our team? Check out our careers page to learn more about our open positions.