Becoming the first design manager

Wells Riley
Jan 31 · 4 min read

As I was transitioning to management at Envoy, I would say “Those who can’t do, teach” as a self-deprecating joke when among my former peers. Stepping up from a four-person design team at a 30-person company to become the first design manager was awkward, at the very least, so joking about it made it easier for me. It made it seem more like something that was happening to me than something I was choosing. I had never been a manager before, nor had I ever worked at a company that had “design managers” — this was completely new territory.

“Those who can’t do, teach…”

I was bummed to be doing less and less design work every day. It got to the point where I’d have to update Sketch every time I opened it — which the team really got a kick out of. Between meetings, hiring, and this weird thing called “Google Docs,” I guess I wasn’t really much of a product designer during my workday anymore. I started spending a lot of time in meetings: one-on-ones with my manager peers, the CEO, my new direct reports. Instead of creating product mocks, I spent my time trying to create a great environment for designers to be creative, own their projects with autonomy, and pitch in to both help the company and their careers grow. I also spent more time than ever on company and team strategy: setting OKRs, building product roadmaps, and meeting with potential partners and vendors.

The secret was that I was actually thrilled with my new job. There was a bit of truth in my joke… I really did feel like the designers I was hiring were vastly better than me. I loved it! Envoy was transforming from a good-looking product to a beautiful one. People who had backgrounds in research and data (two of my weaknesses) helped us make user-centric decisions that vastly sped up our learning and iteration process. We built a culture of friendship and respect, where designers help designers grow and level up their work. Our team is greater than the sum of its parts, and I’m the facilitator making it possible. Instead of feeling proud of my output, I’m proud of the output of others. It’s a wonderful feeling, and more gratifying than I would have expected going in.

How did I get here?

For Envoy, a design manager became necessary. The design team was growing, as was its need for someone to prioritize work across the team, lead hiring, and interface with the other managers sprouting up around the company. Envoy had a successful product under its belt, with another on the way, and change is an inevitable part of growth.

As the first designer, I had already been informally responsible for all of those manager-ish duties at some point or another anyway. When you’re at a small company (like, less than 15 people) you have to pitch in. All the time. At that size, you’re building a business together. Just within my first year at Envoy, I had the following jobs:

  • Sole product designer
  • Project manager for the engineers
  • Hardware prototyper
  • Shipping and fulfillment (for Envoy in a Box… but that’s a whole ‘nother post!)
  • Office manager/janitor
  • Live chat customer support
  • On-site customer support
  • Front-end engineer

Ask anyone else who was around back then… they have similarly diverse job descriptions too. As the company grew, I felt a newfound responsibility (and interest) for leadership. Putting the pieces together, making decisions, and making stuff happen. Even if I wasn’t particularly experienced with each task, the people I worked with trusted me with these jobs.

“When you’re at a small company you have to pitch in. All the time. At that size, you’re building a business together.”

Over time, that trust formalized into new responsibilities. Instead of just pitching in on hiring design contractors or running engineering sprints, it became part of my job. It’s part of the nature of a growing company… oftentimes hiring a Product Manager or VP of Product isn’t Plan A. Before I knew it, I was “Head of Product and Design.”

Was I even qualified to have a title like that?

No. But I learned on the job. I attended conferences, read books and blog posts, and took feedback graciously from my team. It took a bit of time to learn how to do that last one. The reason I’ve only ever worked at startups is because they offer you unprecedented ownership in the success or failure of the company. Everyone is integral. Success and failure are up to you, so it’s your choice how you face adversity.

In my case, it was learning on the job how to be a manager to people who needed a competent manager today. You can only be so patient with your manager when career growth and job satisfaction are on the line. Many people don’t quit their job — they quit their manager. I was fortunate that my peers-turned-directs gave me a wide berth to make mistakes, and shared feedback with me candidly. The trust we had built as a growing team made my transition possible and gave me room to fail. I don’t think it would have been possible without that.

I was determined to be a good manager to these people. Learning, listening, and adapting has helped me recover from awkward moments, screw-ups, and ignorance. As a lifelong learner, I know I still have a long way to go.

Happily ever after…

Startups are terrible if you love neat, happy endings. Not only is my story not finished yet, but my job is still constantly changing as Envoy grows and I grow as a manager. There’s rarely a sense of mastery or completion — every day is different. I enjoy the challenge though! Maybe it’s because I’m still a designer after all. Always analyzing problems, experimenting with solutions, and empathizing with my users. Neat!

Envoy Design

Stories and ideas from designers that challenge the workplace status quo.

Thanks to Katie Riley and Tina Xu.

Wells Riley

Written by

Design at @envoy

Envoy Design

Stories and ideas from designers that challenge the workplace status quo.