Profile: Ben Rosenbaum, Strategy and Operations
Part of our series of profiles of members of our Product Team
Hi Ben! Tell us a bit about yourself.
Hey! I’m Ben Rosenbaum, part of the Strategy and Operations team here at Clipboard Health. I'm based in London in the UK, so slightly different from most of my team. We're very global but mostly based in North America right now.
And what do you do at Clipboard Health?
A lot of the Product team works in specific groups: some are segmented by customer-type like the Healthcare Professionals (HCPs) group or the Healthcare Facilities (HCFs) group - which I’m currently in. There’s also a cross-cutting Marketplace group, and we have Product folks working on New Products and New Verticals too.
In my current seat I'm focused on the ‘core’ of the business, the Customer Operations department. For my first few months at Clipboard, I was mostly leading cross-cutting projects (like launching a new chatbot - one of the main ways our customers interact with us). More recently, I’ve been leading large scale teams across Customer Ops. Previously it was the Payments team, where the mission was to make sure that HCPs got paid fairly and quickly. And as of a few weeks ago, I moved to the Billing team - so I'm now running a team on the other side of the marketplace: instead of paying out the money, we collect the money from HCFs. So it's a different set of challenges, but also super interesting.
Sounds like it! What's different about doing that work at Clipboard Health?
It's very rare for a company of our scale to still be moving as fast as we are - Clipboard feels a bit like the speed of a Series A startup with the resources and scale of a Series C/D start up.
We’re now at the point where we have tens of thousands of customers and hundreds of millions of dollars are flowing through the marketplace. When most companies reach that stage they get bogged down by slower decision-making, lots of red tape, lots of reasons to not do stuff but magically Clipboard has found a way to avoid this.
It’s all thanks to our culture, really, especially the emphasis on extreme ownership. The specific way that translates for me (and others who run teams/projects here) is that I’m able to make decisions quickly and independently. Of course you get a lot of support, probing questions and detailed feedback from people above you and around you (especially on the quality of your thinking), but a lot of discussions are about how you can be unblocked to move faster. For a lot of things, I keep people in CC rather than asking for permission. And they can jump in and say "Wait Ben, that doesn't make any sense, don't do that" (laughs). But for the most part, they don't do that, and it's just really special.
How has that contributed to how you have grown in your role?
I've been given access to opportunities to grow much more quickly than I would have anywhere else. Especially when it comes to leading teams that have a huge impact on the business, Clipboard gave me the chance earlier than the vast majority of companies would have.
One specific area of growth to call out has been around our value of uncomfortably high standards, not just in raising my own standards but learning to uphold those standards across the business. At its core, it’s been about learning to deliver great execution, through ruthlessly prioritizing at a team level and a sub-function level, setting up the right processes and systems, making sure you see things for yourself, and investing the right amount of time into the right areas. Unlike some other places I’ve worked, our values are not just words written on a blog or a wall. And because they mean something, it's in turn much easier to then actually hold people to our values, because most people are bought into them.
One area where we uphold these "uncomfortably high standards" is hiring. You're quite committed to hiring, whether it's at your function level or with your teams. How did that come about?
One of the things we say a lot at Clipboard Health is "Hiring is the single most important thing that we do, because that is our route to bringing in great people into the company". These people are going to have a massive impact, and just keeping the inflow of high quality people is so important.
Over time I’ve gotten more involved in hiring across different areas. There's Product team hiring, and I've also been involved in hiring for a lot of Customer Operations roles. Obviously the nuances of each funnel are different, but there are some common themes. First off, regardless of the funnel, we invest in hiring much more than any other company I've seen or been a part of. We allocate a much higher percentage of employee time to that, because we know how important it is. Another thing - and basically now that I have seen this and experienced that, I couldn't really go back - is organizing hiring around case studies. To me, there are really two reasons that case studies are so valuable.
The first is that it makes it so much easier for us to assess how someone would do the job. Clipboard Health is a writing-heavy culture, where writing is the main way we communicate. And being asked to write a case study as part of the hiring process is a reflection of that. It's a much better signal than a 30 or 60-minute conversation.
The second thing - and you hear this from candidates all the time - is that our process and our cases give a very clear steer on what working here is like. The interview process is designed to reflect our internal working processes, where you would write a document, get feedback on it from your manager, and then discuss the feedback and go from there. So the process is helpful for us, but hopefully also helpful for candidates who can quite quickly make an assessment of whether that is something that they like doing, or if this environment isn't for them.
How was your own experience as a candidate?
It was really fascinating. Before Clipboard Health, my most recent experience was being co-founder of an Augmented Reality navigation startup. While that was a bit different, it was also in the tech startup world.
I did that for a few years, and then decided to take some time off with my girlfriend to go traveling. We were on the move for most of the year, and about three months before I was set to come back, I was in Brazil, and I was starting to think about what I wanted to do next. I knew that I wanted to join a hyper-growth startup. I was exchanging messages with people from Clipboard Health, and I was very close to not going for it, because I was still quite far away from coming back to the UK and I wasn’t sure if I was ready to start applying for jobs.
And then I read more about Clipboard Health. The first thing I did was go to the Culture page and I stumbled upon some of the things we've talked about: the ownership, the writing culture, but also the story of the company, the mission, the success it had, and all that really piqued my interest.
I wanted to learn more, and got to the case study, the Toledo case, which was a super interesting problem. It gave me a real insight into this way to break down a problem "the Clipboard way": analytically and in writing, which I really enjoyed. I then moved forward to the case interview while I was still in Brazil - I chatted with Clipboard in the morning and then went off to see Christ the Redeemer in the afternoon!
I had a similar experience on the Reliability Working Backwards Document. It was also super interesting, and one thing I’ve noticed since being here: you can kind of tell if people enjoyed the problem as they tackled it. Were they curious, did they dig into things, were they intellectually interested in getting to the best answer? So yes, I definitely got quite sucked in (laughs).
Were you looking for a remote role?
I wasn't fixated on that, but I was open to it. There's a lot of startup activity in London, a lot of great companies. But one of the benefits of remote work is it gives me the chance to work for some of the world's very best and most exciting tech companies outside of London. So I wasn't focused on being remote, but I was very open to it.
I was also interested in how it would work, for example the writing culture which means a lot of our communication can and does work asynchronously. Most of the meetings we have - and we are a very meeting-light culture in general - are table reads, where the first ~75% might be people reading and commenting on a Google Doc, then the last ~25% might be live discussion. That means that if you miss the meeting, you can still take part in the discussion by commenting after the fact (or even before). So the writing culture works really well with our remote set up.
Sometimes being in London actually feels a bit like a cheat code. It means I get focus time in my mornings, and helps me structure my day more cleanly. There are phases with lots of people online, with a lot going on in Slack, but having those first few hours where I can do deep work with minimal interruption is invaluable.
You talked about how the meetings we have are rather unique. How do you socialize and meet with your team?
The first thing to say is that all members of the Product team meet in person at an offsite every 3-4 months. That makes a massive difference, because it's awesome meeting the wider team face to face and those weeks are incredibly fun. Another bonus of being in London is that a lot of people come through here. Just this week, my manager was here so we caught up in person. There's always a steady stream of Clipboarders rolling in, so even outside of the offsites and the day-to-day interactions on Slack, I get to spend time with people that way.
But even when we’re not physically together, there’s a real sense of togetherness. A lot of fun Slack interactions. It’s a great group of people here.
What about when you're off work? What do you enjoy doing?
Between 16 and 22 I played poker semi-professionally, I played my way through university and have a few friends that have just been professional poker players ever since. And - bizarrely for someone based in the UK - I love the NFL, which is a bit random, but every Sunday during the season me and my now fiancée, we'll watch the Arizona Cardinals. They’ve been a pretty terrible team recently but I feel like we might be sneaky good this year (for the gamblers among you: this is also what I said last year).
I also love football (as in UK football!). I support Brentford because I grew up two miles away from the ground and had a season ticket when I was a kid. They were a League One team back then and have done so well to make it to the Premier League and establish themselves there. I also love playing board games and computer games, though I don't get a huge amount of time to play either.
Any game in particular you'd recommend?
My favorite board game by a long way is Settlers of Catan. Otherwise, right now I'm playing God of War Ragnarok. It's an amazing game, and I'm nearly done, but I haven’t had much time to play so it’s taken me about six months.