January 23, 2019

Lead(H)er: Emily Glass, Chief Product Officer at Datto

When you have the word “chief” in your job title, you probably have your hands full most of the day. There’s always something to organize, check up on, manage, discuss, and solve.

“You can’t really say, ‘Not my problem,’ or ‘Not my area,’” said Emily Glass, Datto’s Chief Product Officer. “Everything is yours.”

Glass thrives on that kind of pressure. If she’s a little nervous about a new role or project, it just means she’s learning something new. Throughout her career, Glass has sought out jobs just outside of her comfort zone to keep that going.

After graduating with a degree in computer engineering, Glass jumped into product management right away. The field allowed her to use her skills while still interacting with people on a more regular basis than if she had chosen to pursue programming. It also gave her the opportunity to use her background as an artist to weave product design into her roles. At Brightcove, Glass founded a product usability group and worked closely with the product design group. These roles tied her love of art and engineering into Brightcove’s mission to create products that customers found useful and enjoyable.

Glass soon sought out another challenge, switching from design and development into product marketing at Akamai to see what the other side of product entailed.

“I thought that would give me a well-rounded skill set to go to the next level,” Glass said.

She reached that next level shortly after joining Backupify, where she worked her way from senior director of product management to Vice President of Customer Care in the two years before Datto acquired the company. Glass took the uncertainty that often comes after a merger in stride, and her hard work led to the opportunity to run a 150-person customer support group that operated 24/7, 365 days per year.

The largest group she had managed up to that point consisted of about 10 people. Faced with another nerve-wracking challenge, Glass took a step back to analyze her situation.

“When I think about a new challenge, I assess what I've got to work with and where I see gaps, and then I ask for things to enable success, whether it's people or skills or a new office or software,” she said.

Datto is based in Norwalk, CT and at the time, and Glass knew she would be spending a significant amount of time in her new role at headquarters. On the advice of a mentor, she asked for an apartment nearby. It would allow her to think less about what to pack and where she was going to stay during each trip and focus more of her energy on the job. Datto agreed.

“Women sometimes don't apply to a job because they don't think they're qualified, where men tend to kind of go for it,” Glass said. “I always tell women to just apply and ask for what they need to be successful.”

Glass considers advising and advocating for others a critical part of her role as a leader. She works to create an inclusive environment in which minority groups and others who may not feel represented in particular can be themselves.

“That’s how I think we get the best work done because it’s important for people to feel good about themselves at work,” Glass said.

In addition to helping maintain a welcoming community at Datto, Glass focuses on ramping up her product team and ensuring that it’s working to deliver what Datto, and its customers, need for the company to continue growing. She ultimately sees herself as a CEO in the future and considers the role a perfect opportunity to both use her broad skill set and continue adding to it.

“That would be the ultimate learning job,” she said.

Rapid Fire Questions

What do you like to do in your free time?

I have twin daughters that are almost five, so I spend most of my non-working time with them. We read a lot. They're into art, so we do a ton of art together. My travel schedule got a little more predictable, so I’ve just been able to join an orchestra playing the violin. We had our first rehearsal last night, and I'm happy to be able to finally play in an orchestra again.

How do you typically manage stress?

I’m really action-oriented, and I love to solve problems, so I don't really get stressed. When I do, I try to have fun with it. In most meetings I’m in, there’s usually a lot of fun and laughing, even if we’re talking about a big presentation or deadlines. I really think having a solid team is a foundation for good work, so I try to make things engaging.

I also like the technique of putting my worries in jars on a shelf. If I get too overwhelmed, I sometimes will recognize, this is a valid, stressful thing, but I don't need to solve it right now, or it's preventing me from doing what I need to do right now. I'll think about that issue later tonight or whenever I can. I try to handle things one at a time and then deal with the rest later.

I think as a parent especially, a lot of people get stressed about whether they’re succeeding at work and succeeding at home and with all the things they have to get done. You can't possibly be everything to everybody all the time, or win all the time, or succeed all the time. I try to put things in perspective and take longer horizon views about success, that relieves the immediate pressure of any one individual outcome.

How many cups of coffee do you drink in a day?

I drink one cup of coffee, and I am a cappuccino lover, so I'll have usually have a cappuccino or a mug of coffee. I limit myself to one because I drank a lot of coffee years ago, and then I got kind of dependent and decided I didn’t want to go back to that state.

What do you consider one of your favorite spots in the Boston area?

I like Walden Pond a lot. It’s nice to swim across it and walk around it -- I think it's good for a lot of reasons. I used to live in Westford, so I like that Concord-Westford area. It has lots of ponds and quiet places to walk.

What do you consider one of your greatest accomplishments?

Continuing to learn is really what's contributed to a lot of my success, along with my willingness to accept challenges and continue to learn without getting disappointed. I've had failures and setbacks and made mistakes, but I've learned from them and taken a positive approach. Not immediately, sometimes it takes a while, but I’m proud of by and large not letting anything be the end of me or stop me from trying again.

How does where you are in your career compare to where you saw yourself 10 years ago?

Yeah, I think I think 10 years ago I would have been happy running a product management group. I think even though I knew early on that I wanted to work with people, I'm surprised by how much I like to manage people. I think I'm also surprised because it's not exactly what I thought it was going to be. Initially, when I started to manage people, it was challenging, it was not comfortable, and I wasn't the best at it, and maybe I didn't like aspects of it, but I think I'm most surprised that I've actually come to love that part of the job the best. When you're an officer of a company, a lot of the problems are human based. I really like those problems, and that probably surprises me the most.

What’s your advice for recent college graduates?

I think there's a lot of pressure to know exactly what it is you're supposed to be doing, and I felt very much like I couldn't make a mistake or I should choose very carefully because I didn't want to get stuck in a dead end place, or I needed to be in a certain place by a certain time. I think you probably have more time and opportunity to experiment than you think, so don't feel so much pressure to get that first job exactly right. The first job isn’t going to set you up for success or break your career -- it shouldn’t be that stressful. Obviously, you want to work at a place where you love the work, so don't take just anything, but don't put so much pressure on yourself to get the absolute best, ultimate, perfect thing. At that age, I definitely didn't know, and with a little more experience, I found what was the perfect thing for me. Take a job where you can kind of experiment and learn, and find people who are going to support you in that. You probably have a lot more to learn about what it is you want to do, so choose a place where you can do that versus trying to get the best job with the best title.

Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz.
Images courtesy of Emily Glass

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