A Founders’ Guide to Hiring Your First Designer

Designer Fund
Sep 21 · 18 min read

As a founder, you need to hire the right people for the right roles to accomplish your business goals. Recruiting is expensive. It comes at the cost of your most valuable resource: time. And when it comes to hiring your first designer, the stakes can feel even higher. This person will give form to concepts that might exist only in your imagination or as a sketch on a whiteboard. Designers have the gift to bring your ideas to life.

The key to finding the right person for the job is to clarify your company’s needs. This guide will help you determine the kind of designer who will best fit your growing team — and it will help you understand the perspective of other first designers.

I have firsthand experience of this process, both as designer and advisor — I was an early hire myself, joining one of Designer Fund’s portfolio companies, Abstract, as director of design. I have also partnered with founders to make these critical early hires as design manager and advisor at Designer Fund. I’ve watched many designers navigate this unfamiliar terrain and while some have thrived and grown along with the companies they’ve joined, others have suffered from misaligned expectations and not gone the distance.

We’ve created this guide and a worksheet to help your team understand who the right first designer is for your company and how to build an environment where design can flourish.

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Illustrations by Yukai Du

Is it time to hire your first designer?

There’s no universal timeline for making your first design hire. Each company is unique, from the makeup of the founding team to the company’s most pressing needs. “There are so many factors,” says Blake Reary, who has been a first designer twice-over, at RelateIQ (now SalesforceIQ) and Mode Analytics. “There’s the type of business, the type of product, who the founders are and how strong their design and product sense is.”

If you don’t have the design expertise you need on your founding team, an early design hire can guide foundational decisions. But if you do have some design know-how in your ranks, you might be able to wait a bit longer for a full-time hire. However, an early first designer will help you move faster and produce higher quality work.

When Tim Van Damme joined Instagram as the first designer and ninth employee, they already had a product — one that was rapidly gaining popularity. As Tim said of Kevin Systrom, founder and CEO, who had done all the design work until Tim joined the team in 2012, “Kevin had a good eye. They had product-market fit. What they needed was someone to streamline the design side of things. First, I gave the product a visual overhaul, then I focused on UX.”

Waiting this long to hire a designer would have been inconceivable without a founder who possessed some design acumen.

Questions to ask yourself

Is design a blocker?

  • If a lack of design expertise is preventing you from getting your product to market, you need to find a design partner as early as is financially feasible. This arrangement can take different forms depending on your immediate and ongoing needs (more on that in a moment). On the other hand, if you can acquire customers or validate a core technology without investing in design, you may be able to delay your first designer hire until you hit other important milestones, like your next round of funding. “When I joined, Cruise was a 100-person R&D company that needed to shift to a product company,” Stephanie Engle says about joining the self-driving car startup as their first product designer in 2017. This made sense given their specific needs. “Their leadership was focused on their top priority: getting the car to drive,” Stephanie says. It was only by hiring a designer that their focus was able to shift to how customers would access that technology.

Will your design needs be ongoing?

  • Look at your roadmap. Do you have continuous or consecutive projects for a full-time designer to own over the next six months or longer? For most digital products, your design work is never done — as Neville Brody puts it, “Digital design is like painting, except the paint never dries.” You will continue to learn and iterate on your product, which means much of your design work will be ongoing.
  • Do you have several self-contained projects, such as a v1 of a product that will take several months to build and validate before proceeding further? Or do you need to focus on your initial branding and website, to get your product to market? These are great examples of standalone projects that you could outsource to a freelancer or agency.
  • If it’s too early to tell, a consultant can be a great partner in helping define your future design needs. Kevin Twohy, a product design and strategy consultant who works with many early-stage startups says, “When it’s too early to paint a realistic picture of what you’re hiring a first designer to do, it can be tough.” But as he often shares with founders, “If we can work together to get some scaffolding in place, even if it doesn’t live up to your highest aspirations, it’s a starting point. After which a talented first designer can understand your vision and start thinking about how to make it better.”

Do you believe design to be a key differentiator for your business?

  • In 2018, McKinsey’s Design Index tracked 300 publicly-listed companies over five years. Their research demonstrated that top design performers increase their revenues and shareholder returns at nearly twice the rate of their industry. Tomer London, Co-founder of Gusto, another Designer Fund portfolio company, reflects on the value of setting yourself apart from your competitors: “Design is still the most under-appreciated part of what makes startups win. Truly understanding that puts you ahead of 90% of the competition.”
  • For most successful businesses today, design is critical as a strategic differentiator. For example, Gusto was able to gain traction in their market by designing a simple-to-use and trustworthy interface that appealed to their customer base of small business owners. Design set them apart from competitors, whose strategy was to build massive sales teams and focus on large companies. If you’re entering a category where all the other products are painful to use, you could have a competitive advantage and quickly gain early market share through exceptional design, right out of the gate.

If you answered yes to any of the above questions, it’s time to start thinking more seriously about your first design hire.

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Illustrations by Yukai Du

Who is right for the job?

  • Entrepreneurial. Many of the qualities that make for successful entrepreneurs are equally valuable in your early employees. You should be looking for a designer who is resourceful and willing to experiment, who is energized by the idea of creating something out of nothing. Even if a designer lacks specific startup experience, these innate qualities often come through in self-initiated projects, where they’ve needed to consider if there’s an audience for what they’re building. In answering these questions they demonstrate understanding of what it means to build a business from the ground up.
  • Natural leaders. Being a first designer is about so much more than design. “When you come into a company as a first designer,” Stephanie Engle says, “you’re necessarily a change-maker — your role is to introduce the first processes and systems to create a home for design to thrive.” As the first designer, your priority is to ship the first version of the product or brand, which requires establishing how design operates internally. And, as Blake Reary notes, “You need to create a design culture so that you can hire other designers — designers who consider joining in the future will be looking to see if they’ll be entering an environment where there is buy-in and support for design.”

Many founders and early hires have described similar traits in those early team members who had outsized impact. After joining Dropbox as their second design hire and first product designer in 2011, Yi Wei went on to have a nine-year tenure at the growing company. Now, as a Designer Fund advisor, he recommends that early-stage founders look for designers who possess “curiosity, motivation, and humility.” He goes on to say, “If someone has these key ingredients, they can continue to develop other hard and soft skills over time.” These innate abilities — entrepreneurship and leadership — and the natural traits of curiosity and humility will help any first hire ask the right questions and push their findings further, making them a catalyst for change.

What type of designer should they be?

When you are working to bring your product to market or into the hands of customers, you have a lot of different design needs. You require someone with a breadth of expertise. If you only have the headcount to bring on one designer at first, you’ll likely want someone who can own the design for these big projects from start to finish, otherwise known as a generalist.

If you only have the headcount to bring on one designer at first, you’ll likely want someone who can own the design for these big projects from start to finish, otherwise known as a generalist.

A generalist has the knowledge and experience to own each stage of the design process. They are likely not experts in all design domains, but they will have interests and aptitude enabling them to go deeper into some parts of the process. Generalists’ skills will vary, but ideally, they can work on your core product flows one day, conduct user research to better understand your audience the next, and maybe jump in and design the pitch deck for your next round of funding.

Generalists are…

  • Adaptable. They can be deployed on whatever design problems you have today and those you don’t know enough about to anticipate. If your company’s design needs shift in the future, this person can adapt.
  • Autonomous. Since generalists have a breadth of understanding across design disciplines, they can look at a range of design tasks and understand the time/value relationship while prioritizing their efforts and working autonomously. Moreover, they know enough about the needs beyond their abilities that they’re able to hire and manage any contract support.

Keep in mind…

Generalists aren’t specialists in all design disciplines. Although good generalists can run with projects end to end, they’re not going to produce best-in-class work across the board. It’s important that their strengths are aligned with what you really need for your core product experience and the skills on the rest of your team.

Most often, your first design hire will be a product design generalist and you’ll likely need to complement them with specialists for discrete projects as the team scales.

However, there are some scenarios where you might want to consider a specialist as your first designer. As the name suggests, a specialist is a designer with deep expertise in one area of design. This can be a little misleading, because design for most startups refers to digital product design, which is inclusive of many different specializations — research, UX, UI, interaction, front-end engineering, brand and so on. These specializations have a lot of overlap and it’s rare to find a designer who only does UX design, for example. Most (digital) product designers can run the end-to-end design process, whereas a specialist will be able to go deeper into a single part of the process.

Consider hiring a specialist as your first designer when there is a particular design deliverable that is so core to your business’s success that you’re willing to prioritize it above all else. There could also be situations when you need to hire a specialist with deep domain expertise, such as an industrial designer for a hardware product. Or perhaps you need a designer who has a special set of skills in mobile, gaming, AR, VR, and other tech platforms.

Specialists are…

  • Focused. Without the need to continually context-switch, specialists maintain their focus. They may ship fewer projects than a generalist, who is light-touch on more concurrent work, but the projects they do ship will be of higher quality in their specific domain.
  • Process led. These individuals will know more about their area of expertise than others on your team, which means they can drive the process. However, without a broader insight into work happening in parallel, they will likely require guidance on prioritization and managing other dependencies.

Questions to consider…

Think of your first designer as a solution to a specific problem. Once you clarify and define the problems you’re looking to solve, you can narrow down the types of designers who possess the required skills.

Think of your first designer as a solution to a specific problem. Once you clarify and define the problems you’re looking to solve, you can narrow down the types of designers who possess the required skills.

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How much experience should they have?

Most companies want to get their product to potential customers as fast as possible, and a senior designer can arrive at sophisticated design solutions with fewer rounds of iteration. With experience comes speed and better design instincts.

My recommendation is to target designers who have a minimum of four years’ professional design experience. There is a lot of title fluctuation in the industry, so it’s helpful to look at their background holistically — including education and training, internships, self-initiated or freelance projects, and full-time employment.

Designers with limited professional experience will be the easiest to hire. They’re eager and comparatively inexpensive. However, I strongly caution you against bringing on someone with limited experience as your very first hire. Stacy La, first designer-turned-Director of Design at Clover Health, has the same opinion. “I see companies hire a skilled designer,” she says, “but they only have one or two years of work experience, which is a disaster. It’s important that they have some pattern recognition on processes that work and don’t work, and having worked in different environments with different people before.”

The ideal candidate’s background will include experience in both an early-stage environment — where they’ve needed to establish process and define quality — and in a more established company, where they have witnessed design excellence at scale.

Less experienced designers require guidance and mentorship to be successful. Where will this guidance come from? Is there someone on your current team who can act as a hands-on mentor or manager with adjacent expertise (in product, for example)? If you are considering this path, you can bring in an advisor to support junior designers. This also signals that your company is investing in design while you continue to build out the team.

Your budget may limit the type of designer you’re able to afford at the beginning, but it’s very important to think through any tradeoffs that might come with different levels of seniority. You may need to adjust your expectations accordingly. For example, you can’t hire a designer straight out of school, or with a couple of internships under their belt, and expect them to contribute with the same speed and confidence as a senior designer — and have the skills required to lead your future team.

IC today, team lead tomorrow?

Some companies find a first designer who is Head of Design on Day One and responsible for growing the team. However, few early-stage companies can afford to bring on an eventual leader who is not interested in rolling up their sleeves as an individual contributor at the beginning.

When I joined the team at Abstract as Director of Design, I was the second design hire. In the beginning, my job looked very different than it did a year later, when I had a design team of six — which became 14 the year after. I started out by focusing on the most pressing needs of the business, which for a 15-person company was conducting research sessions with our beta users, shipping new features, and facilitating design sprints with our cross-functional team to identify new product opportunities. After our next round of funding, I was able to transition to the core function of most leaders: recruiting.

It’s important to clearly outline the key responsibilities of the role in the first year (and beyond) to ensure alignment in expectations. It’s not uncommon for a first design hire to grow into a Head of Design over time. This can be a draw for a seasoned IC designer who is interested in leadership as the next step in their career. As long as they have the skills and willingness to meet the immediate needs of the business, their responsibilities can expand as the team grows.

How do I find my first designer?

As trained problem-solvers, designers want to understand what you’re looking for and why.

Recruiting resources

Steve Bartel, co-founder and CEO of Gem, has created Startup Hiring 101 to cover all the basics, including step-by-step instructions, example templates, and best practices.

Steve Schlafman and Rishy Tripathy of High Output have compiled the High Output Founder’s Library, a portal to tactical and practical advice, lessons, templates, and resources for founders.

Building an environment where design can thrive

Regular communication about your expectations for the role and the new team member’s performance is essential. Since startups move quickly and processes are constantly evolving, you’re unlikely to have a formal structure for reviews, so these conversations will often take place during your weekly one-on-ones, where it’s helpful to keep documentation of both the company’s and the designer’s goals. It’s also the best container for conversations about growth opportunities, e.g., anticipating the need to shift focus to leadership responsibilities when it’s time to scale your design team.

You can also provide support by partnering with the designer on how they can connect with other design leaders in the broader community. Stacy La received design recruiting support from Designer Fund, and was paired with Airbnb’s Head of Design, Alex Schleifer, as part of First Round’s mentorship program. She says, “If you don’t have leadership support for them internally, make an effort to find outside support. There are many more resources for first designers now than a few years ago, so reach out to investors for programs or connections to help your designers. As a founder, opening your network to your designer can be hugely helpful.”

Bringing on a coach or advisor, like the many advisors at Designer Fund, is one way you can pair your first designer with a mentor if you don’t have such a role internally. You can also provide a budget to attend conferences or workshops, to connect with other designers and leaders; no one understands the challenges of being a first more than others in the same situation at other startups. Stacy La had what she called her “therapy group” of other first designers at early-stage companies. “It can be lonely being the only designer at a startup,” she says, “so having a group of peers I could lean on for support and advice was essential.”

Final thoughts

Much like defining the use case for your business, start your recruiting process with a hypothesis:

To fill the current gaps on the team, I need a [fill in the blank, i.e., product design generalist, with expertise designing UX patterns for a mobile platform].

The more specific you can be with the “why” behind these needs, the better equipped you’ll be to validate your hypothesis. You’ll likely find candidates that don’t check all your boxes, so assess tradeoffs and define the non-negotiables or essential skills you need for your growing team.

We’ve created a worksheet so that you can document your thinking around key questions and share with your team.

By doing the work upfront you accelerate your process and save valuable time. Once you make this critical hire and bring on your first designer, keep the conversation going. Continually assess your mutual needs and work together to meet them. This will give your designer opportunities to hone their own skills or outsource as needed. Invest in their success by providing the support they need to continue their growth.

Ultimately, the right hire will go the distance when their growth coincides with the growing needs of your business.

Heather Phillips is a Product & Brand design leader and advisor at Designer Fund.

Thanks to Kelsey Aroian for your continued partnership and Enrique Allen for your feedback along the way. To all the first designers who contributed to this guide, thank you for sharing your perspectives: Blake Reary, Kevin Twohy, Tim Van Damme, Stacy La, Stephanie Engle, and Yi Wei.

Custom illustrations by Yukai Du.

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