Skip to Main Content

Product Hero is our bi-weekly series that highlights outstanding members of the product management community. These industry leaders share tips on processes, team building, how to be a better product manager, and who they are outside of their careers. This week our product hero is Hill Ferguson, CEO of Doctor On Demand.


Heath Umbach: I’m here with Hill Ferguson, CEO of Doctor On Demand. Hill, how are you doing?

Hill Ferguson: I’m great Heath. How are you?

Heath: I’m doing well. You and I actually go way back, so far back it goes back to high school and I won’t say when that was but suffice it to say that I believe we’ll both agree that we walked both ways uphill barefoot in the snow, right?

Hill: That’s right … certainly long before Skype was created.

Heath: Looking at the time between now and then, you and I have actually taken fairly similar paths, at least right up until the point where you became a CEO. We both ended up in business school, but you were focused on marketing, and I was focused on healthcare management, where you are now.

Hill: You should be here.

Heath: Ha! There ya go! Anyway, we both fairly quickly settled into product management after business school. Can you describe the path you took from grad school to product management to healthcare tech CEO?

Hill: Well, of course I never knew about product management until about 1999. Leading up to that, I had primarily studied liberal arts in undergrad. Part of the reason I wanted to go back to business school was to pick up some new skills and learn what was going on in technology. It was an exciting time with all the innovation happening here in Silicon Valley. I wanted an avenue to get out here because no one would respond to my emails when I was looking for a job. I suppose no one was looking for a political science and Spanish major from the Southeast. So I went back to business school to pick up some hard skills in business and focus more closely on marketing. I was in a special track at Vanderbilt called Electronic Commerce that was centered on people learning how to do business over the Internet.

I spent a lot of independent study time researching how consumers behaved, how marketing would evolve, and how payments would happen with computers. I studied all of the pieces that traditionally go into a commerce process with a brick and mortar retail model and how that would be disrupted with the internet. That ultimately led me here, to Silicon Valley since all of the electronic payment network action was happening here. At the same time I was finishing school, a contact of mine at Yahoo was looking for someone interested in building out a consumer payment product.

I didn’t really know anything about building products, but I did know a thing or two about payments. My knowledge was more academic than from real-world experience, but it was my chance to apply that knowledge. I was able to convince people at Yahoo that I knew enough to be helpful, so I moved out West during the peak of the dotcom heyday. That’s really when I learned all about product management. I hadn’t known it by that name at the time. I really liked creating things with great engineers and designers to help solve a problem that hadn’t yet been cracked.

Heath: Tell me a little bit about how you made that transition from fintech to healthcare. What has that been like?

Hill: I’ve spent the better part of two decades working in fintech. During the beginning of that stretch, people were not using the Internet to move money, buy things, invest, or pay bills. Towards the end of my time in fintech, there was a big wave of consumer adoption and innovation. Nowadays, it’s difficult to find anyone writing paper checks for bills or going to their retail brokerage to speak to someone with printed research. All of those things we now do on our devices. So much has changed.

As I was considering what I wanted to do for the next 20 to 30 years of my life, I looked at two industries: education and healthcare. They are the two industries that have largely been passed by from a technology and innovation standpoint. This company, Doctor On Demand, a relatively young start up at the time, found me. They were looking for a CEO. That was really fortuitous timing for me because I was looking for a change to something completely new and unknown to me. I’ve always been drawn to those types of challenges where I don’t know a ton of context, but I have the excitement to apply what I learned from financial services to this industry. I’m able to have a fresh approach to problems that have been around for a long time.

At the end of the day the consumer is looking for a solution to a problem, not looking to use your product.

Hill Ferguson

CEO of Doctor On Demand

Heath: I heard you once describe how you think about building products. It might be a little different from how other companies or product teams think. Could you tell us what’s worked for you and your point of view on building products?

Hill: A product is really just a solution to a certain problem. There are a ton of different products out in this world. You can define them however you want, but for me that’s always been the most crystallizing definition. When you boil it down to just being a solution to the problem, it really opens the door to a lot of different creative ways to attack that problem. Some of them may be very low tech, some may be very high tech, but at the end of the day the consumer is looking for a solution to a problem, not looking to use your product. I think once you get that kind of orientation about your job, it makes it a little bit easier to simplify.

Heath: It’s interesting to consider how product driven companies view mistakes, so to speak. There’s more of an opportunity to learn by identifying where they may have been wrong in their assumptions. Looking back on your career, what’s an example of a big mistake you made?

Hill: Early in my career as a product manager at Yahoo, we had a partner called Check Free. They powered the back end of our bill payment service. In a rush to get something to market I would often find myself not really communicating as well as I should have with them. We ended up launching a new version of our product, which used an untested API on their side.

The result was Check Free having to roll back a bunch of software on their side to cope with that change. They gave me a very hard time, deservedly so, for that. I felt really badly and really dumb for not pausing for a moment to think about the impacts of change. Part of that was influenced by our culture of moving really fast and shipping products frequently at Yahoo. We always operated under the assumption that you could change something. You can always roll a release back. I didn’t recognize that we had a partner who did not move at the same pace.

The lesson I learned was to understand the full ecosystem of your solution and that, in most cases, it doesn’t just begin and end with you. You don’t have full control over everything. Somewhere along the line there are third parties or other teams that may be relying on a heads up. They’re looking for some type of pre-launch planning activity to easily account for the change you make. From that point forward, I feel like I’ve been a bit more considerate of all the things that can get impacted when you make a change.

Heath: I’ve certainly seen that, more so internally than externally, but I think it still falls under the general headline of, be aware of all your stakeholders and not just the end user. Make sure you’re aware of what you’re releasing and why.

Hill: That’s true, and in fact that experience influenced one of our six core company values here at Doctor On Demand. It’s: be fast, but don’t hurry. That really means never lose a sense of urgency, the desire to run fast, innovate, and make changes, but at the same time be considerate of what the outcomes may be post-change. It’s definitely not been lost on me. It’s been a very valuable lesson.

Be fast, but don’t hurry.

Hill Ferguson

CEO of Doctor On Demand

Heath: That’s actually a perfect segue to my next question: what does Doctor On Demand do?

Hill: Doctor On Demand is the easiest way to see a great doctor. We have a mobile app and a website where you can be connected directly to a board-certified physician via a video consultation in just a matter of minutes.. We have doctors available nationwide and anyone can use our service – with or without insurance. We started out focusing on 18 of the top 20 reasons people go to the emergency room. These reasons aren’t really emergencies. They’re typically cases of the flu, infections, rashes, and other common conditions. We built a clinical practice with world-class doctors who can effectively diagnose and prescribe medication for patients seeking immediate care through a video visit. We have since grown our capabilities to cover mental health with a team of psychologists and psychiatrists. Mental health is a real issue in this country with mental illness affecting 1 in 5 people over the course of their lifetime. We recently announced our service expansion into laboratory diagnostics, making Doctor On Demand the first full-service telemedicine provider to offer fully integrated lab services to over one million patients.

We’re building an integrated physician practice, using state of the art technology and consumer product development practices. We’re bringing that type of consumer grade experience, where patients can access their personal health care system on their mobile device.. Before you had to pick up a landline, use a fax machine, schedule appointments and wait weeks to see a doctor. Once you’re there you wait hours in the waiting room and then not know how much something is going to cost until after the visit. Those parts of the experience are so backward. It’s archaic compared to how consumers live the rest of their lives. We’re changing the status quo by providing on-demand doctors, full price transparency, and a best-in-class customer experience that people just aren’t used to in healthcare.

Heath: What would you say has been the biggest surprise for you at Doctor On Demand?

Hill: I’d say insurance billing, payments, collections, and claims adjudication. I can relate to anyone who’s ever been to a see a doctor and gotten a bill after the fact for far more than they thought they were going to have to pay. Just from having experience in that realm now, it’s not terribly surprising to see this mix up when you understand the level of technology that’s being applied to problems in healthcare. It’s not really engineered to be used the way we’re using it. It’s exciting because there’s so much more room for innovation. These infrastructural standards that the industry has trained people to do such as interpreting eligibility and other things of your insurance plan. These tasks should be automated, in real time, be transparent, and machine readable.

Heath: What keeps you up at night?

Hill: I think the biggest challenge for us, and the thing that I think the most about, is how do we get the word out better about what we do? In our little world, we know exactly about the value proposition that we provide consumers, providers, and payers, but I’m still blown away by how few people in America know about telemedicine, and that  we exist, and know that they can access our product. Tens of millions of Americans have access to Doctor On Demand through their insurance plans or employers and we also have a direct-pay business, with lower pricing than charged in emergency rooms and doctors’ offices.

So, the big challenge for us is educating the market, getting the word out, and reducing the risk for people to try the product. We’re trying to shift consumer behavior in an industry that has been relatively unchanged for decades. Once people try Doctor On Demand they rate us 5-stars, almost without fail. We have a 4.8 average star rating in both Google Play and the Apple App store. That’s over thousands and thousands of reviews, and we take every one of them very seriously. Whole teams jump on any 1-star review and make sure we address those issues. My point is, if we can get you to try the product at least once, we’ve got a loyal customer out of it.

Heath: How do you validate problems you’re trying to solve by testing and soliciting feedback from users?

Hill: It’s a great question. I think no matter where I’ve been or what team I’ve led, it’s always been a priority of mine to get people talking with customers and working with customer service teams, or getting out in the field and actually talking to real life customers. You can never do it enough. It also happens to be probably one of the most fun jobs of a product manager. You do need a little kick in the pants to go do it because there’s always so many things that need to get done in the course of a day. You really have to be prescriptive with your time to make sure you find time to talk to customers.

I’ve never sat in on a customer care call, or a focus group, or just had a conversation with a potential customer where I didn’t come back from that a little bit smarter than I was before. I think that’s single handedly the most important part of the job. I’d also say do a lot of prototyping and sharing of those prototypes with customers to get feedback. from both existing customers and prospective customers.

I think one of the common misconceptions is you have to actually build a working product before you can learn anything. Certainly over the last 15 years there’s been a big movement, at least in the software product management field, around just learning things without writing any code and doing paper prototypes or sketches. Sometimes your product idea may rest on the assumption that someone is going to respond to a certain value prop in a certain way. I think a mistake a lot of people make is building a full product that can complete that full solution. Then they figure out that that’s not what the market wants or needs.

A lot of companies figure out customers only use a fraction of the capabilities of their product. The opportunity is to edit down that product early on to being in a smaller feature set than we may be envisioning for the first step. That is something we all wrestle with: what is enough for the MVP? How do we get something to market fast enough, while it’s still valuable to customers, and robust enough to learn something based on consumer feedback.

Heath: I’m still amazed at how little prototyping has made its way into the common work flow of product teams as a way to de-risk something.

Hill: One of the things that I try to remember is whenever you’re ideating, planning a roadmap, or thinking about a certain new feature or new product, figure out what you need to believe to be true for something to work. If you can reduce those points into questions to get data on, it will help you make a decision. You could be questioning your distribution channel. If there’s a blocker, you save yourself the time of even designing a product since it wouldn’t work there. In the spirit of the Socratic method, ask why. Ask your teams and your customers questions to understand all the assumptions that go into making a successful product.

Heath: How do you guys measure success for your products? What are some of the metrics or the KPIs that you look at?

Hill: Certainly we look for adoption metrics around things like registration, usage, repeat usage, and NPS. That’s first and foremost the most important thing, because we want to make sure we’re meeting a need and turning our customers into evangelizers of our service. Until you have an uptake in usage, it’s not a sustainable business. I think there are a lot of companies that have figured out ways to build businesses around products that don’t actually work. That may work in the near term, but it never works in the long term.

Finding a way to get traction and usage is probably the most important thing, and I think from there it’s more about revenue and ultimately profitability. Those metrics need to be sequenced in a way that give you enough cash to actually create a product that people love; not just use but they are probably going to tell their friends about, tell their coworkers about. Once you get a solid customer base, then I think you can start to worry about other metrics like revenue.

Heath: What would you say is missing in the conversation for product managers right now?

Hill: I don’t think there’s enough to be said about leadership in the job, because as you know, product managers don’t actually produce anything themselves. They may write a spec, but they’re not writing code, they’re not designing experiences with pixels and tools. A big part of the product manager’s job is really about leadership, being able to inspire teams, and being able to arm doers with information around why it’s important to solve this problem.

The times where I’ve had the most fun and have had the best results have been times where I felt like everybody from the team really understood the problem we were trying to solve. It felt like they were really motivated and had the freedom to participate in determining how to solve the problem. It wasn’t about giving them a spec for my genius product and telling them to do something. That rarely works. Maybe if you’re Steve Jobs, you can get away with it for a little bit of time, but most people don’t want to be recipients of instructions for how to do a job. They want to be part of the process to finish that job and to create something great. I think that only happens if you’ve got a product manager who understands that a big part of their job is leadership, creating context for the team, and arming people with data and facts without defining the solution all the way.

A big part of the product manager’s job is really about leadership, being able to inspire teams, and being able to arm doers with information around why it’s important to solve this problem.

Hill Ferguson

CEO of Doctor On Demand

Heath: Pluralsight’s CXO, Nate Walkingshaw, my CEO, and Martin Eriksson, who runs Mind the Product, have written a book called Product Leadership that hits on exactly some of the points that they talk about.

Hill: I can’t say enough about it because I think it’s easy to focus on the technical aspects of the job; how to do Agile, how to run a SCRUM, how to hire, how to do all these tasks. But what’s rarely discussed there is just how do you effectively lead a team? That’s a little bit more nuanced, I think.

Heath: It’s nuanced, and it’s one of the most important, and yet one of the toughest aspects of it. Let’s wrap up with what advice would you offer to someone who’s looking to become a product manager?

Hill: I say just do it. Just jump in and take the opportunity if you have one. I think you’ll pretty quickly figure out if it’s right for you. It’s a job, or a role, that’s still relatively in its infancy. I think of Microsoft as really the pioneers of the technology space, and they really coined the program manager as that title. That’s typically what we all call project manager today. Consumer packaged goods have had brand managers for years and years that focus more on consumer experience, advertising, and branding.

At the end of the day it’s a generalist type job that requires strong leadership, extreme curiosity, the willingness to assume that you don’t have the answers, and actually reveling in that, and never getting to a place where you feel like you have all the answers. You’re doomed at that point. My advice would be just to jump in with both feet and to try it, and you’ll certainly learn a lot. You may learn that, like for me, it was exactly what I felt I needed to be doing with my time and career. Or you may decide that you’d rather do something else. Like any product manager would tell you, you never really know until you iterate around it and try. So, go for it.

Heath: Alright. Well hey, man I appreciate the talk. A lot of good points you hit on.

Hill: No problem, Heath. I enjoyed it.


Learn more about Doctor On Demand by following them on Twitter, Facebook, and LinkedIn. To get more insights from Hill, you can follow him on Twitter.