CTO Corner #2: It’s All About the Mission

I work as a software developer at Jebbit, and I’ll be interviewing new engineering department heads for the CTO corner. Bill Desmarais is the VP of Engineering at Wellist, where his team of four developers builds a platform to connect patients to supportive services. In this week’s edition of the CTO Corner, I talked with Bill about why a company’s mission should be central to everything the engineering team does, how to transition from corporations to startups, and why teams need to be intrinsically motivated.

How did you get into engineering?

I got a computer science degree and math minor at a liberal arts school in upstate New York and then went out to Chicago to work for Motorola. I started my career in QA, and I did a lot of traveling; our product was a big part of building Sprint PCS, so I saw a lot of network operation centers around the country. From there I went to a startup, Novarra — we were a mobile web browsing company — I started writing more code during my tenure there. Eventually, I moved back to New England and joined my first health care startup, Proventys, and then did a stint at PayPal where I managed larger teams. And then I came to Wellist.

What was it like moving from corporations to startups?

The main difference in the role is tied to the maturity of the company. If you’re a senior manager at PayPal, you’re involved in coordinating across teams and supported in HR and recruiting. If you come to a pre-Series A startup, you need to get all these things spinning for yourself while building a product and a team and being responsible for everything.

Did you miss making architectural decisions and coding while you were at larger companies?

I get questions like that a lot, and I think to be effective you have to be pretty hands-on. It’s not a case of missing it because it wasn’t there, it’s more a question of different levels of involvement. When I was hired at Wellist, I was the engineer. If there was something that needed to get done, I had to weigh that directly against hiring someone to do the next thing. It’s not a question of missing it, because if you aren’t hands-on and engaged, then you’re not going to be an effective leader. It’s more a question of having to much more actively manage your day in terms of what percentage of time you spend in different areas.

Being a pre-Series A company, what challenges do you face scaling the tech team?

My number one problem right now is getting the exact right fit in senior engineering. We’re mission driven and pretty small, so we’re looking for someone who wants to get their hands dirty applying their talents to help us improve the patient user experience.

Do you have a stance on hiring talent versus developing talent?

I tend to view an engineering team as a collection of skills. We like to have the right mix of skills. Not everybody has to be the front end expert, but if you don’t have somebody with a serious depth of knowledge you’ll end up against a brick wall. When I am hiring, that’s something that I am actively looking for. That tends to cut across the experience question somewhat. People may be more experienced in some areas and less in others. I describe my hiring philosophy as: Does the candidate know how to do what we need them to do and will they do it with us? We need you to be motivated and engaged and in the mission and want this, so you’ll be fully raring to go every day.

I’ve generally found that you can find people that fit from kind of all engineering backgrounds, traditional and less traditional. And you can always invest in people, helping them to grow the skills the team needs.

How do you keep engineers and people at the company intrinsically motivated and have high confidence in what they’re doing daily?

I try and assess when I am deciding on a candidate what their intrinsic motivations are. If they are a strong mission fit, that’s great for us because we’re creating a thing here and you have to want that thing to exist. But then there’s other sort of intrinsic motivation angles, like wanting a supportive environment to do your best work and wanting to grow with the team. Those are things where I am teaching and helping people grow and I really feel like I did very well previously in my career that I could bring here. That allows you to invest in people and bring them along with you and the company.

What is the relationship like between the engineering department and the rest of the company?

We’re a very small company — engineering is four out of 16 people. The relationship is very good. We work with our product owner on the business side and we discuss on an iteration by iteration basis how we’re going to approach the problem of building our software in a way that helps more people.

Can you talk about how you get knowledge from other departments transferred back to engineering?

We devote energy to it. I should call out the great work of our product owner, Amanda Carbonneau. She and I are responsible for really synthesizing that stuff into an engineering roadmap. Maybe there’s a feature we need to close a deal at a hospital versus a feature that we came out of a user feedback session — our product owner and I collaborate almost constantly doing our estimates, ranking things, so the engineering team can just go, go, go.

How do you get user feedback?

This is another great way that the mission alignment really helps us, because a lot of this stuff you can kind of intuit from your passion for the space. We also cultivate an advisory user base and we do a lot of user testing. We put things in front of them, and then get feedback and change our designs.

Is there such a thing as too much data?

No. The simple answer is no. If the right person is looking at it and you know how to slice it and dice it and ask honest questions, the data will tell you a great deal. And we’re supporting people as they get well — we need to constantly be learning from whatever data we can get, so that we can build our technology and help people find the services they need so that they can focus on getting well.

What makes an innovative leader in the healthcare industry?

In my experience, a good leader cares about getting the best results, cares about eliminating barriers to getting good results, and recognizes that cultivation of the team as a whole and the people on that team is what’s needed to get results. It’s investing in people, caring about people, keeping skills up to date, and trying to make sure you’re aware of all the new innovations that can be brought to bear on the mission you’re trying to accomplish.

It was not only until the last couple months that I began to understand and work closely with marketing — was there anything that surprised you about marketing? Or maybe any other departments?

Every person in a company this small has a very important role to play. Marketing has to find the right way to engage the customer, sales has to worry about proving to hospitals exactly how much better their patients lives will be with our technology, the product people have to be focused on building the right things as well as they can and shipping, shipping, shipping.

How do you keep up with new technologies and trends?

I keep track of Hacker News, programming subreddits, and I have a very good group of professional acquaintances and we talk shop. That’s the most interesting one: keeping abreast of what people you care about in software engineering are doing.

Where do you think tech is heading?

I think guessing what’s going to come along is a fool’s game; I hope that it keeps being brought to bear to disintermediate, to more directly help people. Leveraging technology to solve problems that matter to people — I am optimistic that is where technology is going. The details of that are anybody’s guess.

What’s your best advice for future VPs and CTOs?

I encourage people to figure out what their core is and how that can be most useful to reducing human misery on the planet. If you are in a position to become a CTO or VP of engineering, you’ve got a lot of experience, so use that well, invest in the people who will help you, and keep your eye on the prize.

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