Demystifying the Founding Designer Role

Being a founding designer at a startup can be equal parts exciting, chaotic, and fulfilling—but it’s always a challenge. As a designer, how do you decide if it’s the right move for your career, and if you’ve found the right opportunity? Maybe you’ve been at a startup already, but you’re ready to take on a leadership role. Maybe you’ve been at an agency and you want more hands-on experience building a product or service. Maybe the world of start-ups is totally new. Regardless, hearing directly from designers about their experiences is always the best place to start.

We hosted a conversation between Aly Agoff, Director of Design at True Link, Northstar's Head of Design Dennis Cortés, and Primer's Founding Designer Elizabeth Lin—each of whom have extensive experience designing at startups—to delve into some of the ways designers can be intentional about how or if they join a company as a founding designer. What follows is an excerpted conversation, with additional insights from Tara Kelly’s wonderful book “First Designer In” and Designer Fund’s co-founders Ben Blumenrose and Enrique Allen.

Key topics we cover:

  1. What does a founding designer do?
  2. How do you choose the right startup to join?
  3. How do you prioritize your mental health?

What does a founding designer do?

The best founding designers are strategic, flexible, collaborative, and organized. They may be required to step in on branding, marketing, product design, research, or fundraising — sometimes all at once. And all the while, help the broader team understand the true value of design.

1. Brutally prioritize

“You need to be really good at prioritizing, almost brutally so. No one’s going to tell you exactly what to do, and they may not know what design should even be doing. I’m a yes person, and I want to do it all. But if as a founding designer you try to do it all, you’re going to burn yourself out.” – Aly

“Going back to prioritization, it’s about being comfortable with things being less perfect than I’d like them to be, and identifying where quality will have the most impact.” – Dennis

Let me be very explicit: being the first designer in is a metric ton of work. It’s a heck of a lot for one person to shoulder. Therefore, every move that’s made needs to be leveraged for the greatest benefit. Tara Kelly, Author of First Designer In

💡 Pro tip: Ask yourself—what are the top three things that matter? If you struggle to get to that list, or something new keeps getting added, re-evaluate if you have the right information or inputs.

2. Embrace ambiguity

A founding designer is often someone who’s resourceful, willing to experiment, and gets energized by the idea of creating something out of nothing. As Yi Wei notes in our Founder's Guide to Hiring Your First Designer, "designers who possess the key ingredients of curiosity, motivation, and humility can continue to develop other hard and soft skills over time.”

“You need to thrive in a space with lots of ambiguity. There’s a million question marks around you and you have to be able to be ok deciding which question mark to work on each day. You also have to enjoy creating the process instead of just going with the flow, because the process is always changing.” – Elizabeth

💡 Pro tip: Practice taking action and executing on projects—even when you don't have all the answers. When in doubt, get early feedback from your team and especially customers.

3. Be a generalist

“It’s been really helpful for me to be a generalist. I’ve had to do branding work, product design, illustration, marketing, and hiring. Because of the limited amount of resources you have, you can’t necessarily contract the work out. Most of the time, you need to roll up your sleeves and figure it out.” – Dennis

“Though a founding designer starts off as a solo practitioner, they must also represent the entire design function. Someone with a narrow speciality would be hard pressed to carry the weight of moving the company forward using only the power of their design skills, because you need a lot of different skills to pull that off.” – Tara

Among the broad set of skills that founding designers need to be able to cover, Tara recommends that they perform at least competently in the following areas, should the need come up:

  1. Discovery Research
  2. Testing & Validation
  3. Information Architecture
  4. Experience Design
  5. Interaction Design
  6. Visual Design

For more details, check out First Designer In

💡 Pro tip: The path to becoming a great generalist starts with taking the time to develop specialized skills. As Spotify's Siri Johansson notes, "you do that by following a path you’re passionate about, staying open-minded and absorbing tangential knowledge and skills along the way."

4. Build smart systems

Another one is documentation and organization—things you may not be passionate about, but need to be able to keep up. As the founding designer, it’s important to develop the context, stability, and culture for future team members coming on. To do this, you need to write things down, documenting your process and the decisions you’ve made from a product perspective.

“I might be biased because I enjoy working on them, but it’s also helpful to be comfortable with design systems. It creates the foundation, not just for the design team, for the product as a whole. Creating that stuff early on as best as you can is incredibly helpful because you’ll be able to work much faster, especially with engineers.” – Dennis

💡 Pro tip: When thinking about how to build a design system from scratch, take a page from Alissa Briggs' book and start by "tackling the low-hanging fruit, demonstrating the tangible benefits, and eventually getting the buy-in needed to staff out the team."

5. Build the business case for design

“I consider the impact that I want to have and how it fits into the company strategy. And telling the story to stakeholders: To be successful in getting my work prioritized and gaining buy-in from stakeholders, I need to be able to say ‘based on Y data, we should try X, because its going to help us get closer to Z goal.’” – Aly

“One of the biggest opportunities I've seen for designers to increase their influence is to demonstrate how their work aligns with the success of the business. By articulating the value of your work, you can secure more resources and buy-in from your organization and thus ship more work.” – Enrique

Design is still the most under-appreciated part of what makes startups win. Truly understanding that puts you ahead of 90% of the competition. Tomer London, Co-founder of Gusto

💡 Pro tip: The ability to define and communicate design’s impact on the business can pay off in spades. To learn how to use design as a strategic business partner at your company, check out our workshops, along with our case studies featuring companies like Airbnb, Dropbox, and Pinterest.

How do you choose the right startup to join?

1. Look at actions, not just words

“You need to look at the actions and where the resources are going, versus what they say. We’ll often talk to companies that say ‘oh, we totally value design.’ But you ask, ‘how much have you invested in design today?’ And they’ll respond, “we haven’t really had the time so far.’ So you really want to see that money is invested in design time and design actions taken. If you don’t see that, that’s a red flag.” – Ben

“For me, a really good sign that design was going to have a seat at the table at Primer was that they were looking for a designer as one of their first hires. It was on their list from day one.” – Elizabeth

💡 Pro tip: Take a close look at how the company is organized. Will you—as the founding designer—have a strong voice and seat at table? Will the company give designers ample budget to build the right team and invest in creativity?

2. Talk to the team

“Aim to identify the design advocate or ally during the interview process. Is there at least one person on the team who has a clear sense of why design is important, and specifically: what problems they’re looking for design can solve?” – Aly

“Start with the ‘why?’ when you talk with the founders and the rest of the team. Ask them to articulate the mission and what gets them up in the morning day after day. Do you think they genuinely believe in the purpose of the company and does it strike a chord in your heart?” – Enrique

💡 Pro tip: Use scenarios to really test a team’s willingness to make tradeoffs or work through competing needs. Ask them to talk through how decisions are made and how collaboration actually works at the company.

Questions to ask yourself (and the team) when evaluating a startup to join:

  1. Does the company have product-market fit? What’s their current growth rate?
  2. How much runway does the company have, and what are its future funding plans?
  3. Do you trust the founding team to lead the company to success? What does their track record look like?
  4. What are the company’s long term goals? What plans do they have for the design org?
  5. What are the company values and examples of those values in practice? Does their culture align with what’s important to you (e.g. collaboration, work-life balance, D&I, impact)?

For more, read 5 Questions Designers Should Ask Before Joining a Startup

3. Test it out

“Freelancing gets you exposure to lots of different industries, working styles, and cultures. It helps you understand what you do or don’t like, and there are opportunities to join teams full-time as their first designer. ” – Aly

“If you can, if you’re the first designer, consider doing a trial hire and working with the team or with the founders for a month or two. And during that time, don’t just deliver designs, but really try to figure out what the team dynamics are: how are they making decisions and pushing back on new ideas? Make sure it’s a real project that’s supposed to go into production on a deadline.” – Ben

💡 Pro tip: “At Primer, we do something called a work trial where candidates get paid to come in and work with us for 2-3 days. It helps give us a really good signal on how someone might fit in with the team.” – Elizabeth

How do you prioritize your mental health?

A conversation about startups and founding designers wouldn’t be complete without the mental health piece. The role, after all, can a little bit lonely and taxing at times. Here are two key tactics for managing stress and taking care of your mental health, especially when balancing the many responsibilities required of a founding designer.

1. Build community

“Communities are huge. A few founding designers at other education companies and I met up for a weekly group chat where we’d send screenshots of our work, discuss what we were working on. Finding those people in similar boats and creating your own places to get feedback is really helpful.” – Elizabeth

“Even as a solo designer within the company, you need not be alone. There are multiple opportunities to interact with the design community, if you take the time to seek them out. As designers we have the advantage that our peers tend to be heavily empathetic. Our community can be exceedingly helpful, often selfless, in their desire to give back." - Tara

Design communities to join:

2. Find balance

“As a founding designer, you’re likely to get burnt out pretty easily because there’s just so much on your plate. For me, it’s about remembering that I work to live—I don’t live to work.” – Dennis

“Another thing that’s been helpful for me is recognizing the flow or cadence of my process. It’s not always linear: sometimes I’ll have a sprint of intense work, as a big deadline or workshop approaches. I often feel tired afterwards, so I’ll let myself have the space to take that Tuesday off. I’m a big fan of working smarter, not harder. So get the crunch time in, but give yourself time to breathe.

I also gravitate towards creative things like quilting and playing Minecraft. Hiking—getting away from the screen to move and have the time to think—is also such a nice shift for my brain. It’s a relief to not have to do anything other than move forward.” – Aly

💡 Pro tip: Guarding your time is easier said than done, but you can start by creating transparency around your workload and communicating it with your team up front. At Northstar, for example, Dennis created a Notion board around the design org’s projects and tasks so everyone else at the company can see what the team is working on at any given time.

At the end of the day, know thyself

From shaping the UX to building the design function from the ground up, the founding designer role is one that comes with great responsibility, uncertainty, and potential for massive impact. While joining a startup as its first design hire is a major decision, the most important is to know yourself—and decide if it’s the right role for you. That’s why we’re so grateful to designers like Aly, Elizabeth, Dennis, and Tara for giving us their honest insights and sharing a peek behind the curtain.

For further reading

About the contributors

  • Elizabeth Lin is the Founding Designer at Primer, an online place for kids to find learning communities based on their interests. She's currently based in New York and enjoys playing the saxophone and all things related to fashion.
  • Dennis Cortes is the Head of Design at Northstar, a financial wellness company where he leads our design efforts and works on the product. Outside of work, he makes music under the name Cordio and is a big fan of traveling, plants, animals, Pokémon, and food.
  • Aly Agoff is the Director of Design at True Link Financial, leading efforts across the business in growth, product, research, and marketing. Having spent a lot of her time in Fintech, she's passionate about using data to create delightful and intuitive designs that democratize and modernize antiquated, inaccessible industries.
  • Tara Kelly is the author of First Designer In. For over a decade, she worked as a designer in the startup world, making a career of being the first designer hired, then building up a team from scratch. So she wrote a book about it. Tara enjoyed writing so much that she's taken a hiatus from employment to explore publishing, writing multiple children's books under the pen name Kelly Tills.