Brian O’Hagan: Leading with Empathy, Innovation, and a Commitment to Give Back

Driven by a commitment to lifting others up and using technology to solve meaningful problems, Brian O’Hagan, currently Director of Product at BetterUp, brings empathy and curiosity to every role he takes on. In his Member Highlight, he reflects on his experience leading products at Vimeo and Warner Brothers, giving back to the product community, and the advice that shaped his approach to learning.?

Your career has spanned multiple industries so far. Can you walk us through some of the major milestones?

Brian: My career actually started in higher education. I worked for a group at a university for quite some time—we were asking hard questions about technology, trying to understand its impact on teaching and learning. My focus there was on building cutting-edge, multimedia-based tools and interactive media experiences for teachers and students.?

Eventually, I realized I wanted to work on things that were utilized by more people, so I made the jump from the edtech space to Vimeo. Because of my background, I immediately fell into the project management responsibility, overseeing different products there before moving to Warner Brothers. That was at the beginning of their push into streaming, when they were building all sorts of bespoke video services for their properties, including DC Universe, which we developed in partnership with Comic Con. Delivering a streaming service at that scale was eye-opening, but even though I thrive in fast-paced environments, I realized that being at such a big company wasn’t the right fit for me, so I made the move to Skillshare.?

Earlier, while I was still at Warner Brothers, I had taken a coaching course with BetterUp, and I was really enamored by their concept. They were always on my radar, and when I had the chance to join their team as Director of Product, it felt like things were really coming full circle. Because in edtech, the challenge for me was always answering the hard questions about technology—like, all this stuff is flashy and cool, but so what? What’s the why? What are we actually doing with it? I feel like we’re working on answering that question at BetterUp. We’re trying to bring together science, humans, and technology to help people and organizations grow, while also tackling those hard challenges in tech that not a lot of companies are working on.?

What’s your approach to learning and staying agile?

Brian: Today, there’s almost too much information out there to absorb and pay attention to. I see it as a good challenge to figure out what you want to focus on. I do think you have to follow your intuition—to ask yourself what your curiosity is drawing you to and make the time to dig into it and explore it deeply.?

What does that process look like for you?

Brian: To me, learning is an active process, not a passive one. I’ll read about something and then immediately look for ways to apply it in real life. When you throw yourself into something like that, you learn really fast. In my case, I also feel like I do my best thinking in the mornings, so I try to reserve that time for thinking, processing, and exploring new ideas.?

Is there any professional advice you’ve received that’s played a major role in your career development???

Brian: I remember this time when I had just arrived at Vimeo—at the time, there were only about 50 people working there. They were making the push to turn it into a real business, but there was no product management there at the time. I was basically the first real PM at the company. Leadership kept throwing all these great product oversight opportunities my way. Eventually, they asked me to lead this whole new initiative around transactional video. I was excited, of course, but I also felt like, “I’m out of my depth—maybe I ought to go to business school now.”?

What the president of the company told me was, “Do this for the next two years. That’s your business school.” That advice was huge—and it was so true. I mean, you could do a training program, or you could go get an MBA, and you’ll gain a bunch of great knowledge, but you still have to learn how to do it for real, right? That experience ended up being my real-life business school.

What brought you to Sidebar, and what’s been your experience with the platform?

Brian: I would say my motivation for joining Sidebar was twofold. I wanted exposure to new people I could learn from and grow with, but I also wanted a way to give back to others. It’s been a difficult economic climate for so many people, especially in tech. A lot of people in the product community are between jobs and facing uncertainty about what comes next. I’ve been there before, so I try to make a habit of connecting with one person every week to give them attention, advice, connecting points in the network who might help them… What I really want is to be a listening ear and a hand up to help others find their way, and my Sidebar cohort has given me an opportunity to do that. I find so much fulfillment in that. That’s what gives me energy.?

Any final thoughts or advice you’d like to share??

Brian: Learn by doing. No matter how much you read or prepare, sooner or later, you have to take the plunge. That was something I learned early on: You only really earn your stripes by getting in there and doing it—figuring it out, failing hard, learning fast, winning big. That’s what levels you up.?

?? Join Sidebar today to connect with inspiring leaders like Brian and gain insights that can propel your career and personal growth.

Learn more here!