Alyssa is a product designer with a primary experience in health-tech design. After graduating from Massachusetts College of Art and Design at the height of the pandemic in 2020, she worked for innovation labs at Massachusetts General Hospital, a Harvard iLab startup, and now, Swapt. She lives outside Providence, RI, with her long-term boyfriend, their puppy, and their bunny. 

Frederick Daso: What was your journey to becoming a Product Designer at Swapt?

Alyssa Donovan: I’ve been a one-woman design team since I started my professional career. In college, I interned at the Healthcare Transformation Lab (HTL) at Mass General, where I got to dip my feet in product design through physician-facing apps. It was tough at first, not having other designers to critique my work, but I eventually found my groove and realized it wasn’t a bad thing that I got to make these creative decisions on my own. I’m a learn-by-doing person, so getting thrown in the deep end was the only way I would have figured this out. Being in an innovation lab also meant I was working on things that didn’t exist yet, so there weren’t a lot of design standards to go off of. This helped make me a well-rounded designer—being there through every step, problem-solving, and making things pretty. I’m grateful every day for that.

Shortly after graduating in 2020, I took on a full-time position as a product designer at Vincere Health, where I was tasked with using design to help people quit smoking. Being the only designer, I got to do the entire process—interview users, execute user testing, iterate on designs based on their feedback, and create a unique style for the company. I found a love for early-stage startups here and grew tremendously as a designer with the support of the rest of the team. Everyone would attend my weekly design meetings, which helped me learn how to talk design with non-designers (and vice versa!).

Andrew, the CEO of Swapt, and I have been friends since high school. Earlier during my college years, he had significantly influenced me in continuing my education and taking my future more seriously. So, when he and his co-founder, Trevor, approached me with a product design opportunity at their new company, I trusted their vision and decided to jump on board. Now, I’m here at the very beginning, building app, and brand designs from the ground up, and I love it!

There’s a lot of conventional career advice about being a successful Product Designer, but are there any unorthodox lessons you’ve learned through experience or been taught through mentorship that more of your fellow designers should know?

Donovan: Some important lessons I’ve learned in the field so far are:

1. Communication is key

Dev teams work in mysterious ways, but that doesn’t mean they can read your mind. Know what is and is not possible.

2. Don’t be afraid to defend your design choices

You’re the professional; you know what you’re talking about. That doesn’t always mean you’ll be right, but at least explain your choices before you ditch something you’ll inevitably have to re-make.

3. Don’t marry yourself to your designs

Investing personally in designs will only lead to trouble. It isn’t a personal attack when people say they don’t like something you made. Take that moment and use it to better your skills.

4. If it isn’t broken, don’t fix it

We’re at a point where there are some layouts and interactions that people generally understand and are comfortable with. Don’t make your users solve something new to use your stuff.

Daso: What’s the toughest project (professionally or personally) you worked on as a Product Designer or in general? What were the most important lessons you learned from that project?

Donovan: The toughest project I’ve had to work on as a product designer was probably the Vincere app. What made this project difficult was the range of the target audience (20’s–60’s) and the complexity of the process we were trying to guide them through. Users in such a large range have very different understandings of tech, and it was sometimes difficult to decide how to convey the steps in a way that everyone could follow. I think the beauty of being a product designer, though, is that the product doesn’t end at the app. 

The program included a Quit Kit with a CO-detecting device, some goodies, and informational cards. The cards ended up being a vital piece to use in tandem with the app to guide users through the process of doing a breath test and their journey through the program. At Vincere, many of my projects came with this kind of user range, and it helped me learn to simplify complex issues into easily digestible pieces.

Daso: Who are some of the most inspirational people you’ve gotten to work with during your career in tech? 

Donovan: I feel like I’ve learned big lessons from everyone I’ve worked with; it’s hard to pick a few! 

My first mentor, Victoria Vacaro, was the most influential in my career and life. I reported to her at HTL, and she taught me to be confident and strong at work. I was 100% terrified of her when we first met, but by the time we left HTL she was more like a big sister. She’s the type of person who can hang with anyone and not be intimidated. She’s decisive, intuitive, and a force to be reckoned with. 

Another person who’s been inspirational to me is more of a two-for-one from Vincere, Shalen De Silva, and Jake Keteyian. These two are the most real leaders you’ll meet. They always think of the team first and are so hands-on with every aspect of the company. They went out of their way to keep us up to date on anything involving the company, and that kind of connection kept the team as strong as it was.

Daso: How would you define your company’s culture, and how does it create an environment where you can do your best work?

Donovan: Swapt’s culture is endlessly positive, supportive, flexible, and casual. I do marathon-style work, so as long as I have a deadline, I’ll make it, and Swapt 100% enables that. It’s great to leave my desk when I have a creative block and return to it later. The whole team is also super eager to help; even if they have a million meetings daily, they’ll make the time to solve any problem. 

Daso: What are the most important skills you’ve had to develop in your job, and what specific projects or assignments did you work on to develop each core skill?

Donovan: Some of the most important skills I’ve had to develop in my job were:

1. Time management

It is so, so easy to toss hours at any little piece of a design. But this removes the final product when you lose sight of the whole. At the beginning of my career, I wanted every draft to look perfect, whether in my sketches or prototypes. I’d love to say I suddenly became good at managing my time doing these things, but it took actual effort. Something that helped me was using the Pomodoro technique to force myself to reach small goals in specified time increments. Eventually, it became a habit, and my productivity improved immensely. Sometimes I’ll get bogged down in the nitty gritty like I used to, but I’m much quicker at nipping it in the bud than before.

2. Communication

As I mentioned before, communication is key! Going from presenting my work to all designers at school to essentially no designers in my professional life had a learning curve. In presenting my work at Vincere and HTL, I learned how to explain my choices and promote conversations amongst the team. The more I did it, the more fun I had brainstorming with everyone. I think that everyone is capable of contributing to a design; whether you’re the only designer or not, it’s a group effort, and that effort is made stronger by a common language. I encourage input, and I try to make it clear that they won’t hurt my feelings. It’s so easy to overlook something when you’ve been staring at it for weeks, and it’s awesome to get others’ perspectives. In many ways, I find it easier to design things for users by getting this feedback from my colleagues because they’ll tell me when something that seems intuitive to me makes no sense.

3. Flexibility

Working at startups usually means you will wear many hats. At first, it can seem daunting having all these different jobs that appear to demand the same urgency. The hardest part about this was learning to switch working modes. I can still get really into a project and lean into heads-down work, but I’ve taken on more of a chameleon-like working style. It’s hard to pin down one project that I can attribute to this, given the nature of the lesson, but I think a good recent example would be jumping between designing the Swapt website and copywriting for it simultaneously with Trevor. 

Writing and designing are both creative things, but I spent so much time typesetting that the words and content started to look like shapes to me and I was struggling to focus on one or the other. This area is where working with someone who isn’t designing all day is extremely helpful. Trevor was able to help workshop the content with me, and after working on it for a while, I was able to transition between making sure we had content that both made sense and fit into the layout I was developing.

Daso: What’s one interesting thing (non-work related) that more people should know about you?

Donovan: I never lose rock, paper, scissors.

Daso: What’s something you want to accomplish in your career that you haven’t yet? What motivates you to get there?

Donovan: There are two things I currently have on my career to-do list:

1. Take on a design leadership role

One day I’d love to lead a team of designers. Seeing what’s possible with just one designer makes me think about how much could be accomplished with a team.

2. Teach

There are so many things I’ve been learning since I graduated that I think are important for future students to know before entering the field. Not that I was unprepared when I graduated; it’s more so that this field is constantly changing and morphing, and knowing how to navigate that is key.

Frederick Daso
Frederick Daso