Remote Work Interviews

Owl Labs (OL): Tell me about how you got to where you are in your career today.

Zack Cleary (ZC): I've been working in technology for years. Early in my career, I was focused on building nationwide wireless communication networks in emerging markets. As soon as I started doing that, I found that I loved being involved in technology and how it can bridge gaps and bring people together. From there, I started building software and eventually became an entrepreneur.

I realized that what I loved the most was working with teams with a shared set of common values and goals. And building those teams to accomplish those goals was fulfilling. As an engineering manager, I essentially build engineering teams and scale them -- that's what brought me to Ro. We're doing things I believe in with a fantastic team and a great set of founders. My passion is building that team so we can continue to solve problems in the healthcare space.

OL: At Ro, the mission is to reinvent healthcare. How are you doing that?

ZC: There are potentially many ways we'll be doing that over time, but we've been working on some exciting stuff at the moment. At Ro's core, we believe there are a lot of different areas to focus on. Healthcare is a big space and there are many problems to be solved. One of the most important ones we've been focusing on is patient safety. The patient always comes first at Ro. Transparency is another core pillar of ours. We think the medical space is one of the hardest to navigate, especially during a time of illness for you or your family.

You have to go out and collect information to learn about your condition, which can be a lot to handle, and very challenging. Whether it be price or seeing the outcome of your procedures, transparency is a big focus.

Another way we're trying to reinvent healthcare at Ro is through access -- from costs to being able to access a doctor from anywhere, be it from your phone, desktop, or in-person. There are several areas we feel we can innovate to create an ideal healthcare journey for people in a way they haven't been able to experience before.

OL: What have you learned about disrupting systems by building products at Ro? How are you able to use innovation to make an industry that's so entrenched easier to navigate for your customers and your clients?

ZC: At the core, technology has given us the chance to disrupt a lot of existing industries. In our case, we don't think about disrupting the structure, but rather, we think about augmenting it to create the best possible experience for members. There's an enormous amount of technology in the American healthcare system that's incredible and works very well, but unfortunately, people don't always get the best experience in their journey.

We've tried to build a full-stack technology environment, where we thought if we owned the entire healthcare journey for our members, then we'd be able to innovate at any part in that journey. We built everything from the online diagnostic platform to the physician system and the pharmacy platform. Because of that, whenever we see a part of the user experience or the medical experience that we don't think is ideal, we feel it's our obligation and the right of the member that we do everything we can to innovate and create a different and better experience.

OL: You also have sub-products that focus on specific women's health and men's health issues. How are you choosing the health challenges to tackle and prioritize next?

ZC: We're entirely member-driven in that regard. Based on either the data or the conversations we have with our members, we recognize where folks are having a hard time in the healthcare system, and those then become the challenges we try to tackle. We specifically look at challenging areas of the healthcare system and hold ourselves responsible in-house because we feel we can create a better healthcare journey and outcome for our members than the existing solutions can.

OL: Let's talk about the folks at Ro. What industries do they typically come from and what sets them apart in tackling these big challenges? What's the culture at Ro like?

ZC: It's the most incredible team I've ever had the opportunity to work with. I think the best part of it is that we're all from a bunch of different backgrounds, working together to solve a shared problem or to answer a shared vision. From the very beginning, one of the coolest parts about Ro is we were a team of just four or five people in a room. At that point, we already had a set of principles, values, and qualities every Ro employee would have.

When you have a principle and value-driven culture, everybody knows what their goals are and what they're laddering up to. We're trying to change and innovate in the healthcare space, and we all know how important our mission is. Everyone here truly cares about what we do. In some places, you might hear engineering teams say, "Move fast and break stuff." Well, we do try to move fast, but in our world, we won't break stuff. We have to care about every single member's interaction, we have to care about their healthcare, and we have to consider almost everything we build to make sure we deliver the best possible product.

OL: What are your company values?

ZC: There are a lot of them! The main ones we look for are effectiveness, relentlessness, and an extra bit of curiosity and pizzazz. It's a little extra magic that makes the everyday work special. Everybody at Ro looks for that both in each other and in our colleagues, but also in the work we do.

Empathy is a core value for us as well. We always have to consider the end-user or member, depending on who they are and what they do in their daily work. But we also consider the people we work with and how they'll consume the outputs of our work. Whether you're writing code and someone has to use the systems you build, or you're writing specs for a story on the product team, you have to assume the engineers will be able to consume it.

All of us have to understand the background of the people we'll be working with to determine how to communicate the work we're doing to the other groups.

OL: Do you have fully-remote workers or a hybrid workforce where people sometimes work from home? What does that breakdown look like at Ro?

ZC: It's a core part of who we are here at Ro. We know talented people may be anywhere in the world for various reasons, and we want to work with the most talented people who are capable of addressing the challenges we're trying to solve.

The engineering team is a mixed model. We have some people co-located in the main offices, but we also have a team spread around the world. Our distributed team is very much a core part of the greater team -- it's not an outsourced model. Everybody works in what we call "squads," and we're all working as one unit, no matter where we are. We also have daily stand-ups and all the normal ceremonies, but then we have a lot of tools as well to make sure the distance feels as little as possible. Of course, people get alone time because they get to work remotely, but they also always feel like a part of the company and included in all major events, all company happenings, etc.

OL: What are some of the tools your distributed team lives and dies by?

ZC: One of the beautiful things about a remote team, especially for engineering, is it forces you to be explicit, rather than implicit. When you work in the same room, you can say, "Oh, well, I know Sophia knows about this thing, so she'll know what to do next." In a context where employees work remotely, you have to make sure the whole team has those same facts written down in the same context with the same information.

To do that, we use a series of tools. The product team is very active in Asana. The engineering team is 100% in Jira. All tasks, all work, all estimates, all stories, and all tickets are planned out in Jira. We heavily rely on Slack and Google Docs as well. We spend a lot of time using Google Hangouts, and many times just chatting with each other on Slack. The Meeting Owl is also a big part of our business. It's in every single conference room to make sure the distance feels as little as possible.

OL: How do you make sure remote employees feel included in the team culture at Ro?

ZC: There are a number of things we do in that territory. One of the main ones is a rotation policy, so any engineer on the product team who works remotely can come to New York and feel a part of the culture when they need to. During onboarding, we try to get people together in person, and we use a buddy system with new employees. Everybody who onboards, onboards with someone who has been on the team for quite some time. It's not just to show them through the work but to say, I'm here for you during your journey in getting familiar with the company and what we do here.

We also have a bunch of different team events. We have an all-hands every week, which is one of the company's main principles and values in making transparent decisions at every level. By sharing information as openly as possible within the organization, more people will be able to make good decisions on their own teams. Because of that, we have a very open culture about sharing information from every level of the organization. At our weekly all-hands, for instance, we always have both a video recording and a live stream. Everybody is encouraged to communicate and talk at any point in the conversation. We use microphones and Ro'ers always speak one at a time, enabling remote Ro'ers to hear every word.

We also do social events in New York, and the company's thoughtful about saying that, no matter where you are, we'll help you to do the same thing at a distance. Let's say the New York office has a happy hour. For the team that might be in Florida, we'll give them the resources to hold a happy hour there, or they can go to a sporting event or something else fun. Then, there are a lot of simple, small things everybody does naturally, like sharing photos and giving high fives virtually. We have an active "shout out" culture, celebrating people for their successes at the company as a way to highlight people and their accomplishments. It's people shouting out their colleagues for incredible demonstrations of great work or camaraderie.

OL: Does the location of other remote workers on the team influence your hiring or are you fully location-agnostic?

ZC: It depends on what you do. In Florida, we have our pharmacy fulfillment team, so you have to be physically located there to do that. Other parts of the team on engineering, for instance, are spread around the world. We have at least 12 time zones covered at this point. We have a number of people we work with in Poland and other parts of Eastern Europe, we have a couple of people in California and a number of people in the New York time zone.

We have a distributed team, but not everybody is remote and those aren't quite the same, right? With distributed teams, there may be offices all around the country. The remote part is having people either work from separate co-located spaces or home offices. There's a lot of that, but it's most prevalent on engineering and product teams.

OL: Product and engineering orgs can sometimes be staunch about making sure the product manager is in the home office to work with so many of the different stakeholders, so it's interesting that's where most of your distributed and remote folks are.

ZC: We iterate on it as we do on everything else in the company. At different stages, you need to adapt your strategies. In our case, we found a way to make it work. We like to have some representatives from the team or squad, in the office so they can speak to their initiatives firsthand. However, we've seen a lot of the remote teams outperform by not being distracted by the office work, specifically in engineering. It's incredible to be around people and have firsthand information, but sometimes a tap on the shoulder when you're deep in a problem-solving scenario can be tough. You need deep solitary work time to get things done.

OL: What's a myth about remote work that you'd like to dispel?

ZC: A lot of people are intimidated by the prospect of rolling out remote work, which I think is short-sighted. Working remote builds a lot of great habits, it can force a company to be very disciplined, which helps especially when you scale. When you are five people alone in a room and you're sharing a similar idea, you have a general sense of what's going on. But when you're in that same room with about 20 people, it's hard to keep the communication going the same way unless you make it intentional and active. Remote work pushes on communication and transparency from the beginning in a way that's helpful if you want to take on a big project and solve big problems down the line.

There are certain markets where there are outsized opportunities, but talented and capable people aren't always there. Since the business is in New York, the notion that you'll find all the best people to tackle that challenge within a 20-block area doesn't appreciate all the incredible people out there who can make a difference. I like the idea of building teams with great people who are excited by a shared mission, regardless of where they are. If you can do that, then you can find the tools to make it work.

OL: I think the growth of online education and the growth of remote work will democratize the New Yorks and the Silicon Valleys of the world. It's a smart way to be planning for it now instead of reacting to it five years from now.

ZC: You see a lot of large-scale technology teams moving to a motto of, "our new office is the world." You hear that mantra right now because the reality is that's the way the markets are working and where the opportunities are available. We've finally built all these tools, we built the internet, and it's working great. We're using video conferencing software now having this conversation. It does take learning some different practices and behaviors but if you lean into it, you can do some amazing things.

OL: What do you love most about what you do?

ZC: For me, it's the people I work with. As the team grows, the tech is exciting. If you have a good group of people in the room and they're given the tools and the time to solve problems, there seems to be no problem you can't solve! I get super excited about the people I work with, and I do everything I can to build an environment where they can use their core capabilities and expertise without the roadblocks on the way to tackle the big problems in healthcare.