This interview is with Gemmy Tsai, product manager at OpenTable. (Download the audio recording of this interview.)
- UC Berkeley undergrad
- Monitor Group
- FTV Capital
Q. Tell us about your background.
A. Sure, I’m 27, I have a bachelor’s of science in electrical engineering and computer science from Berkeley; I have worked in management consulting at Monitor Group, as an investment associate at FTV Capital which is a growth equity firm, and currently I’m a product manager at OpenTable.
Q. Tell us how your career path brought you to your current role.
A. Growing up, I had always thought I was going to be an engineer, and going to college I studied computer science and engineering and thought it would be the case there as well. I did my first internship after my sophomore year as a programmer working for Bank of America. And that was my first exposure to tech and the programming side, and it was that summer I realized that while I love technology, I really couldn’t see myself as a developer sitting in a cubicle and doing that for the next 10 to 20 years.
So I came back to school my junior year thinking about what would make sense given that I’m studying engineering but I probably don’t want to be a programmer for the rest of my life. I heard about consulting, where a lot of people said it’s something where, if you don’t know what you want to do, it’s a great thing to get into, you can learn about different companies, markets, and different types of problems. And so I did my internship after my junior year in consulting for Monitor Group, and went there full-time after graduation.
At Monitor, I did some pretty general marketing and corporate strategy projects, helping companies think about growth, new markets to enter, helping them think about how best to market to their customers. And it was through this process that I realized I really liked the business side of the world. But I always gravitated toward technology projects, and we worked for a couple large tech companies in Silicon Valley, and I really enjoyed those projects. So I decided I wanted to get some more focus specifically in tech, as opposed to Monitor which was pretty general. The other thing I felt was that, with consulting, it was pretty high level — you walk in, make some recommendations, and drop off a PowerPoint deck, but it’s never very tangible in terms of actually helping to act upon your recommendations, or helping see the results of a recommendation.
So I thought about what opportunities would be interesting, and one of the things I started reading about was the idea of investing. And what attracted me to it was that it was very tangible in the sense that you make a decision, you put your money where your mouth is, and you see the very tangible results of whether you were right or wrong about that decision. That’s what drew me to it at the beginning. There were also a lot of positive attributes, similar to consulting, where you’re constantly looking at different markets, companies, industries, and talking to different people — it’s still a pretty broad skill set.
So that’s how I moved into investing. I did that for almost three years, and through that process, I realized I still love tech, and tech is where I wanted to be, on the business side of technology — but it was still not very tangible. So I had started in consulting trying to find something a little more tangible, got a little more of it in investing since we were working directly with companies and putting investment dollars at work. But we were always still at the board level talking about strategy but never actually helping to implement things ourselves. So I wanted to find something where I could actually help build something, help create something from the bottom up, and see the results in a very tangible way. I knew I wanted to stay in tech and I had personal interest in the consumer side of technology. I also felt product management specifically was an opportunity to help build something where it wasn’t at the developer level, but I’d still be able to help shape the direction of a product, help conceive it from the very beginning all the way to market deployment, that entire process. That’s how I ended up deciding on product management, and eventually that’s how I ended up at OpenTable.
Q. You went from consulting to investing, then from investing to product management. What specific steps did you take to make each transition?
A. Sure, so for the first transition from consulting to venture, the things that helped me most were identifying relatively early on in my consulting career the general direction where I wanted to go. I knew I wanted to stay in tech, and I knew I wanted to do something on the investing side. So I tried to figure out how my experience at Monitor, which was pretty generalist, could set me up for success for my job hunt.
One thing I did was to push for as many tech-related projects as possible. I spent a lot of free time reading about technology to make sure I would be able to speak intelligently about trends and issues going on in the industry. Additionally, one of the biggest challenges of people going from consulting to investing is the finance skill set, and being able to prove you know how to think about financial models and returns and the concepts of investing, at least at a high level. And for me, especially as an engineer, it’s easier for me to convince VCs and other investment funds that I had the technical chops given my CS degree, but less of the finance aspect. But Monitor actually has an arm which is a little more finance focused, where they focus on corporate finance, M&A, thinking about growth in terms of inorganic growth, acquisitions, helping companies think about strategy for acquisitions. And within that, there was a lot of modeling for M&A. So I pushed for myself to get into that group to get some of that financial experience, and that proved really valuable because I used a lot of concepts I learned there in my interviews, and it was really helpful to talk about. Because fundamentally, we were helping companies think about investments to make in new markets and new products.
So for me, it was helpful to think about where I wanted to head a little bit early so I could plan ahead and tailor my Monitor experience to get me where I wanted to. I was also lucky because I had a good mentor at Monitor who was thinking about moving over to venture, and I piggy-backed off him, so identifying mentors early on was helpful.
To make the transition from venture to product, it was about 30 times harder. One big challenge was the fact that a lot of people don’t know what venture associates do, so it’s not very tangible and people don’t specifically recruit for people who have been associates in venture. So just explaining that, and clarifying what my skill set is, was a challenge. The other thing was convincing people that I could actually get down to the nitty-gritty enough to actually be a product manager — to have the technical understanding and the day-to-day tactical skill set and willingness to get your hands dirty, which frankly you don’t do as much as a consultant or investor.
So what was most helpful here was that I was able to draw on my consulting experience, which was a little surprising to me. But not being afraid to think about experiences that aren’t necessarily your current experience, but the one before that or potentially even two steps back, and thinking about what skills those experiences bring that can help you transition is helpful. In my case, there’s a little bit more of a framework out in the job market for what consultants do versus what VCs do, so that was really helpful.
And finally, in terms of switching, the value of my network was super valuable. So thinking about what companies I wanted to work at and who I knew at those companies. At the places where I didn’t know anyone, recruiters wouldn’t really give my resume a second look because it’s such a different profile than what they were typically hiring for product managers that it just didn’t make sense. So I really needed to get somebody who knew about me and knew what I could bring to the table to push me along a little bit to get me the opportunity.
Those were the biggest challenges, and also just finding the right role. Product managers at OpenTable tend to be less technical than product managers at some companies where you have to be a coder, or you have to be very strong in technical background. So finding the right role and niche within the broad spectrum of product management where my skill set was appreciated was a challenge.
Q. It sounds like for both transitions, networking and mentoring was important.
A. Yes, super important. When I went from consulting to venture, I actually went through a headhunting firm, which was fine. But there wasn’t a similar set path for the transition into product management. So that’s where I had to really dig deep into my own network.
Q. What did you learn about how to network effectively? Any best practices you can share?
A. My take on networking is really not networking for the intention of “what can I get out of this person.” When I think about networking, it’s more around connecting people, and how to help people you meet. So one of the most effective things I think you can do when you network is to connect people you know, who don’t know each other yet, but who could benefit from knowing each other — just being helpful whenever you can, and being someone who is interested in and willing to help somebody, rather than always thinking about what can this person give to me, it really should be the opposite. So that when you actually do need something, then that relationship has already been built.
So it’s really thinking broadly and not being too laser focused. I’m in tech, so there is a tendency to only meet people who are doing startups, food related things, commerce related things to build my network. But you never know who knows whom, so just keeping an open mind, and being giving rather than taking, is one of the biggest I learned in trying to network.
Q. What is it like to work at OpenTable? What do you do day-to-day?
A. I help manage our consumer website and try to help figure out what new features we want to build on our website. I spend a lot of time around some newer products — so rather than our core reservationing system which most people are familiar with, more around new opportunities that OpenTable can get into, whether it’s in the deals and offers space, where we’ve tried a couple things, or it’s around loyalty programs, things like that.
It’s probably better to look at my role on a weekly basis since my day-to-day varies quite a bit. Typically we have a morning stand up / status meeting with our engineering team, understanding the progress they’ve made, any barriers they have, any questions they have for me. My role as a product manager is to ensure our engineers are able to make as much progress on our product roadmap as possible, so I support them in that effort.
I also usually have a couple meetings per week with the product team as a whole. We talk as a product team about what everyone else is working on, how it all fits together, we try to give people suggestions on each other’s product roadmaps, and get feedback from each other as well on the direction of the different pieces we’re working on.
A big part of my week is also planning meetings. Every other week, we start a “sprint,” which is a two-week time period where our engineers work on a set grouping of tasks that are relevant to our product roadmap. So we have these planning meetings and we talk to the engineers about what we are envisioning for the website, and then we dive in deeper — for instance, this is the specific requirement for this specific webpage, this is the specific requirement for this button, for this new offering. So being very specific around the requirements and actually going through the process of sizing and estimating the scope and then actually doing the task planning for the next two weeks to accomplish the goals we’ve set out.
And then we spend a lot of time with our business side — our marketing and business development teams, to discuss initiatives they have that they would like product support on. So a new product we need to build to support a new idea, some product support to integrate with a new partner we’ve been talking to. A lot of meetings with those teams to understand their priorities to drive the business forward, and how I as a product manager can tailor my roadmap to reflect the priorities of marketing, business development, and our CEO.
And then lastly, I try to find some time for myself to do some reading and thinking around the products I’m working on, research on the competition, spending time with my own products in looking at analytics we have and doing as much research as possible so that I’m informed as to how my products are doing, and what’s a good direction to take the roadmap into the future.
Q. What is most exciting about the role?
A. We’re involved with some of the most important decisions we make on our consumer website. So we’re in conversations with the executive team to think about the strategy and direction of the product. And then we have to take that all the way down to the engineering level, and very tactical requirements. So that’s actually very exciting in being exposed to both high level and low level stuff, really seeing that entire process of how does an idea turn and go through all the different steps through the entire organization into something that’s launched a few months later.
The other things that’s interesting in terms of what I’m working on is that, while OpenTable already has a core business that they’ve mostly figured out, in terms of taking reservations on the website, there is still a lot of opportunity beyond that. So we view core reservations driving the main business, but we think there’s a lot of opportunity for other potential offerings for people who like to eat out. So I’ve had a chance to be involved in some of those initiatives, and it’s interesting to think about ways for this company to innovate. It’s just exciting generally to be able to shape the product direction of the company and feel like you’re making an impact on where the company is going.
Q. If you could change one thing about your role, what would it be?
A. One of our challenges is that we are actually a 12-plus-year-old company. So despite the fact that we are a venture-backed company and have a little bit of the Silicon Valley feel, we’re still a fairly old company by Silicon Valley standards.
So there’s challenges that come along with that — an older code base, for example, where sometimes we’re not able to move as fast as we’d like to because of all the things that have been put in place over the last 12 years in our technology. So I’d love to wave a magic wand and be able to flip a switch and instantly upgrade our technology to something completely modern, which would help us move as fast as the business demands. We can’t right now, but there’s definitely opportunity for us to try to improve that.
Q. Where do you see yourself in the future, and how will what you’re doing today help you toward that goal?
A. I’ve enjoyed both my experiences in product management and investing, even though they are so different from each other in terms of the people, the culture, the pace, and the scope. Longer term, I could see myself in either direction, and it’s not clear to me right now which path is the right one. But in the shorter-term, I definitely see myself continuing to do product management, because I really have enjoyed it, and potentially finding an opportunity to build something that’s a little less defined, where things are little less figured out. And then longer-term, whether it’s back to investing or actually owning a P&L or a business unit or even running my own company — essentially tying together the experience I’ve had across investing, consulting, product and my engineering background, to actually own a piece of a business or an entire business going forward.
Q. What advice do you have for people who are interested in a role like yours as they navigate their career paths?
A. Sometimes it can be daunting to think about a career transition, and I frequently hear my friends talking about wanting to switch careers, but not acting upon it. I think sometimes it can seem really daunting to make a switch into something completely different than what you’re doing now.
So I’d say one of the biggest things is to not be afraid to dive in. Because one of the most helpful things in figuring out what you want to do is to actually just start the job search process. When I was in investing and thinking about the next move, it wasn’t crystal clear to me that product management was the right move. But as I started talking to friends, reading job descriptions, doing both informational and real interviews, and just talking to people to understand different roles and what I would be suited for in terms of skill set, what types of companies would want me, and what’s important to me — that process really forces you to do some introspection as you dive in, thinking about what companies you want to work for and where it makes sense to spend your time doing your job search. It really starts making things more tangible.
The criteria I ended up with at the end of my job search was to find a company that was a few hundred people, medium-sized, fast growing, in the consumer space, where I could do product management. But three months before I took my job at OpenTable, I had no idea what any of that was. That really came as a result of talking to people and researching companies. You really can’t just sit around and think “blue sky” about where you want your career to go. I really think you have to dive in and get dirty and talk to people and do interviews before you can figure that out and learn about yourself enough to know what you want to do. To me, that’s the biggest thing.
I also found it helpful to identify from the bottoms up the companies I wanted to work for, rather than specific positions I wanted or just combing through job descriptions to see what was available. Often the most interesting positions aren’t readily posted online, so looking bottoms up to identify the 5 or 10 companies you’d really want to work for, and thinking about who you know at those companies and how to reach them — that’s often the best way to find roles at those companies that are suited to your skill set as well as your interest level.
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