The bridge to Head of Design

Illustration by Raul Gil for this article.

Nobody warned me how challenging being the Head of Design at an early-stage startup would be. Then again, nobody warned me how much I would love the challenge.

How did I get to this point?

The journey started for me over a year ago. I had spent a small part of my earlier career managing a team and after a number of years I found myself longing to get back to that. I wanted to feel again what it’s like to not only design products but also business groups, organizations, and the processes around each.

There is no more significant design task than getting a group of people to work together toward a shared objective, growing and evolving as they go.

Additionally, I found myself wanting to be in a position much closer to the core business of the work I was doing. I wanted to not only and continue to see design's impact on customers and products, but also get close to the metal and manage how the function of design impacts and influences a business's bottom line.

What is the bridge to head of design?

As a creator, I feared moving into management would mean missing out on time spent actually designing things.

For many designers, moving into management means exactly that: the end of making. Managers tend to miss out on being close to the craft and instead must dedicate their time to helping manage and lead the team. Meetings, managing calendars, presenting work and representing the team, negotiating with executives... I wasn't sure all of that was what I wanted to do with my time as I started exploring my next career move.

Then Nick Bushak, CTO and co-founder at Gem, reached out for coffee, and through conversation with him I had a revelation. As a Head of Design I could spend a good year or two in a player-coach position before having to decide which path I'd like to take more long-term.

Being Head of Design at an early stage startup often means building and managing a design team from the ground up while also doing the work expected of a very senior individual contributor. You have to do both because both are needed at the early stage and small size of a series b company. As the company grows, the need to balance both managing and designing subsides as new members join the team, eventually pushing the Head of Design into either a senior designer role or focusing on management as a Director of Design.

Moving into the role of Head of Design meant I would be tasked with identifying headcount, hiring, defining what the team's purpose is and how we’ll operate, what parts of the product development process design is responsible for, and creating a vision for how we would grow. It also meant I'd have ample opportunities to get my hands into the work because the design team would be small early on, but the work required of us would be plentiful. I'd be not only a coach for the team but a player too.

Of course, a Head of Anything in a startup faces obstacles and issues you don't get if you are only an individual contributor or a manager.

At the bridge between both manager and individual contributor roles, you face challenges at both ends.

If you’re acting as both manager and designer, how do you know when to focus on team building and processes as opposed to focusing on the craft itself? How do you show up to lead and manage the team when you're also spending a reasonable amount of time showing up as a designer too? Where do you draw the line at being a partner to your team and their manager? Possibly most important: how do you help others on the team (the design team and the leadership team) understand what to expect of you if you're constantly doing both leading and designing?

To answer these questions I did three things immediately upon joining the team at gem:

  1. Set out to define what matters most to me as a leader
  2. Sought to understand what matters to the company in a leader
  3. Sat down for 30 minutes with every single person in the company to learn of their perspective on design, the most pressing needs as they saw it, and what they wish design would tackle first

As part of a Stanford class on leadership, I outlined my leadership values (what my team and peers can expect from me as someone guiding a function in the company) before starting the role. I then created an outline of how I see the design team role functioning, based on early conversations with other design leaders I had developed connections with over the past few years.

Alongside guidance from my manager, Nick, I was able to identify where I should spend my time and draw lines between the tasks ahead of me as a new Head of Design. (I also found this article from McKinsey to be very helpful.)

Each of these things helped set expectations around the role for both myself and the broader company.

Crossing means expanding and refining skills

Moving across the chasm between individual contributor (or IC) design and management meant facing many skills and problem areas I never had to think really, truly, deeply about before. Things like:

  • How should a design team be structured? What roles does the team need inside the company to be most effective? What's the right time to bring in specialists vs. hiring for generalists?
  • How do finance and talent teams play a part in the planning of a team? How do you negotiate the importance of a role on the team?
  • How do you find and source high-quality design candidates to join the team this early in its formation? (Product plug here, because Gem is making this process a little easier!)
  • What work is most pressing for design, and what work can wait? What will help the business achieve its immediate goals, and how will that work be prioritized against more long-term investments in user experience?

As a result of some of these questions, I started the job at Gem by focusing my time on two core areas:

1. Capitalizing on immediate design wins

Immediate wins for the company were easy enough to tackle as a former IC designer. I spent a few weeks up-front auditing the entire product, talking with every member of the company, and working directly with customers to understand what design work needed to be done right away. I asked: what could help demonstrate the value of design to the company while getting me familiar with the product, customers, and culture? Within a few weeks, I had shipped minor but readily apparent changes to the product and begun shaping processes around the role of design as a function.

2. Preparing design to scale and create business influence

Scaling a design team was a new space for me to work in. I never had to think about building and scaling a design team as an IC. As such, I relied on external resources and help from other design leaders in the industry to spotlight the skills I would either need to improve in or learn for the firs time. Amongst the skills I identified:

  • Business strategy: How does our product solve real needs in the market, how are we growing our presence in the industry, what are our strengths and areas of opportunity as a business? How do we establish ourselves as leaders and convert that presence to dollars? What is design's responsibility for each of these things?
  • Organization building: How do we get the most benefit from a team of people? How do we align business objectives with team structure and career planning for individuals? How do you hire designers for a rapidly growing company?
  • Communication, negotiation and product strategy: Three skills not only belonging to managers, but skills I hadn't needed to become truly an expert in previously (as my peers in engineering, product management, and design leadership could fill in my gaps for me as an IC).

Most helpful for me during this time of identifying skill gaps was having a personal "board of directors" I could reach out to. Whenever I encountered a challenging situation or whenever I'm unclear about something as it relates to my role, having this close group of people I can seek guidance from has been rewarding.

Being in a Head role can be overwhelming and leave you feeling like you're on the verge of failing at any moment. There’s so much to be done and only one you. Having a small group of peers who have done the role successfully before can be all the support and inspiration you need to stay afloat.

First brought up for me during the DesignX State of Leadership panel. The idea is simple enough:

  • Find people in the industry who have successfully done what you're doing now
  • Build a close connection with them
  • Regularly meet with them to glean insights from their experience

Surprisingly, not a single design leader I have reached out to over the past year has declined time to chat. Many of those conversations have grown into regularly recurring catch-up calls.

Without this personal board of directors, I'm not sure I could survive the dynamic world of a fast-paced startup, let alone the role of attempting to cross between management with designing at the same time.

What it means to grow a design practice

As many of the people the design team works with at Gem haven't worked with a product designer one-on-one before, I found it essential to live our company value of transparency and make the design process as straightforward and clear as possible to everyone in the company. This emphasis on working transparently is great because it aligns with my personal values as a creator and leader.

Early on at the company I started hosting weekly, hour long, Design Reviews on Fridays, inviting everyone in the company to attend and see a bit of my work process. The company at this stage was very interested in the topic, and I found upwards of 90% of the company would regularly attend these virtual meetings to see what this new “design” function was all about.

Over time as the design team has grown, I've pushed for us to continue this practice of transparency in other ways.

As a design team, we share work daily in Slack. We host Design Reviews each month for discussion with anyone in the company who wants to attend. We also host weekly Open Office Hours for anyone in the company to ask questions and work with us collaboratively—in real-time—on problems. These things have helped connect design to the business and demonstrate how our function does much more than just turn an ugly screen into something pretty.

Scaling the team and lessons learned thus far

One of the biggest focus areas in my role is thinking about how the design team will scale inside the company.

Kristin Skinner and Peter Merholz wrote a book on designing the design organization in a company, in which they outline a time-tested process for building and scaling a team.

The book, aptly titled Org Design for Design Orgs, is an excellent reference and helpful guide for any organizational leader who needs to understand how design might scale in their company. Though the book is a good reference, it's also relatively generic and requires deep thinking into what your specific company might need as it scales. For Gem, this meant looking at the company size, product-market fit, and investment in the product itself.

As I thought about building the team, I landed on hiring strong design generalists first, then scaling to include specialists (across design functions like writing, research, motion, and interaction design) later. By focusing on generalists out of the gate, our small team could work in a scrappy way to accomplish whatever needs to get done quickly. The outputs of this small group’s work may not be ideal or perfect, but when it comes to a startup, done really is better than perfect. If you’re not moving quickly—producing work, snuffing out fires, and focusing on scaling—the competition is always there in the wings waiting for their chance in the spotlight. Design generalists are exceptional at moving quickly, no matter the task.

During the first few months at the company, I also learned just how difficult hiring can be.

I've participated in interviews before, but have never been responsible for defining an open role, writing the job post, creating a rubric for evaluating designers, and putting together an interview guide.

When it comes to hiring, that's not all: during the first few months of looking to hire designers, I had to actively reach out to potentially strong candidates and show them why joining a small, early team like Gem design was a good move, even though externally it can seem very risky as a career move. It’s a hard sell for many designers who cherish stability and certainty over the potential reward of being an early leader at a growing company.

General wisdom when it comes to hiring is to go with who you know. Close connections—the people you have worked with before—are easier to hire for and more reliable in the long-term but also introduce a ton of bias. I knew from the start I wanted to build a diverse team of designers from many different backgrounds and expertise areas, not just from my network of former colleagues at big tech companies like Facebook and Lyft.

So, after countless months of talking with designers, reviewing portfolios, calibrating the hiring team, making offers only to have them declined for various reasons, we landed two incredible designers within my first eight months on the job. Melinda Kilner and Wandi Liu joined the team, and each has contributed heavily to the overall makeup of how we work and what it means to be a team. I could not be more thrilled with both of these designers and the work we’re doing together to build the foundations of what will inevitably be a truly world-class design team.

If you’re hiring designers you can’t be afraid to hire from smaller companies than the big FAANG ones. You should look for designers with strong processes, adaptability, creativity, and grit. You may be surprised what you find when you give a conversation a chance.

Of course, having such great designers on the team has meant my perspective of leading them has evolved as we continue working together and scaling the team.

When we say "head" of the team, I now view that as helping to gently nudge decisions, demonstrate practices and processes, and provoking meaningful discourse and debate for both the team and individuals on it.

I've learned an incredible amount in this role already. I've learned about startups and how to both show up and not show up as a leader (those messages you send on Slack intended to be witty and humorous, for example, tend to have a different punch when you’re a leader). I've learned about the way design can subtly influence decisions inside and outside the company (a vision workshop can be helpful for driving vision, but only if it’s regularly referenced).

More than anything: I've learned I made the right decision bridging the gap between IC and manager. Because in this role, I've discovered my passion for getting to know the individuals I work with so closely daily. I've uncovered just how incredible (and incredibly hard) it can be to get people aligned and doing great work. I’ve learned from my team, and I’ve seen the mistakes I’ve made in the past as an IC designer. I’ve grown a lot, partially out of ambition but probably more so out of necessity.

I now wake up every day both excited and anxious for what the day holds for me in this role. Where will I fall short? What new obstacle will I uncover and have to maneuver around? Am I making the right decisions for my team and the company? Am I contributing in a way that is helping move the bottom line? Is this road going to be one I want to stay on for a long while? Only time will tell.

For now, I'm loving it all. The challenges and opportunities.