Head of Design, 2020 —2022. As Head of Design and the first design hire at Gem, I established the design function, built a distributed team of designers, and helped the company grow 5x in size and reach a $1.2 billion valuation.

Establishing the function of design

When I joined Gem in 2020, my first task was to introduce the new design function to the company and set up processes and rituals to enable future designers to succeed.

To establish design, I first conducted a series of deep conversations with all 70+ employees. I asked everyone I spoke to three questions:

  • What do you think the purpose of design is?
  • How have you worked with design in the past?
  • What should the immediate responsibility of the design team be at our company?

Through these conversations, I identified themes and needs across the business. The existing Gem team wanted the product to look more modern (unlike the outdated version of the free, open-source code Bootstrap they were using). They wanted the company brand to be updated, and they wanted help in researching and exploring solutions to business and product problems. In other words, design's role would be to modernize the brand, up-level the existing product design, and create business systems to enable high-quality future product design.

To fulfill these needs, I created a year-long roadmap of how the new design team would focus and contribute. I worked with executives at the company to ensure the roadmap aligned with expectations—using the same language I had heard in my interviews, so everyone at the company felt like a contributor to the plan. I then set out to put my strategy into motion.

I comprised the roadmap into five phases, each with example projects and an estimated timeline for achievement:

  1. Establish design within Gem. Work transparently to share design processes and outcomes and amplify design thinking in the organization.
  2. Catch up to the existing product by creating Gem-ified design standards. Work with stakeholders to define and align on "What is good design?"
  3. Expand design by evolving existing features using the new standards. Work on the backlog of existing features to meet the newly defined standards.
  4. Align completely with ongoing product and engineering initiatives. With existing features updated, work to have design partner with engineering and product management on new features.
  5. Envision future product improvements and strategies. Show design contributions more extendedly by sharing concepts and research early.

A year after creating the roadmap for the function of design, I completed all five phases. I brought the entire company along with me as we hired designers and built new processes to embed product design practices into the existing business. Design became evident in Gem's product culture, a visual and collaborative function with clear value.

One core element I wanted to bring to Gem was conveying how the role of design can add value outside of product or brand work. There were ample opportunities to pull design into projects at varying levels, from preparing slide decks for the Gem board to creating custom swag for celebrations. One of the more impactful projects I worked on was the design and development of a visual, holistic journey map for our target customers. Through this visual map, all Gem employees were able to align on the needs of our customers and begin using the same language for the various problems and opportunities Gem was solving.

Gem employees spend considerable time talking with customers. Still, we needed a way to visualize and align understanding of what our customers go through in their jobs (i.e., Jobs to Be Done or JTBD). To give the team a tool they could use when talking about our customers, I spent a week auditing customer calls, working with key stakeholders and experts in the company, and iterating on this comprehensive journey map.

Much later, after hiring the first few designers for the team, I realized one of the most rewarding parts of being Head of Design was building and strengthening the role of each designer. I spent considerable time building a design hiring rubric, outlining our interviewing processes, talking with designers, and ultimately hiring a genuinely remarkable team to work on all aspects of design at the company—from design systems and principles to team rituals and branding.

As more designers began to onboard at Gem, I often took time to recognize their contributions deliberately and openly. Designers at Gem have helped establish design team rituals such as critique and weekly stand-ups and dramatically influenced how the Gem product looks and feels.

To fully empower designers on the team, I thought of myself as more of a guide and coach than a mentor or hands-on manager. This empowerment often led me to learn a lot about myself and the design process, but it also meant I could work closely with designers whenever they needed my insights or expertise. A typical project might start with a product manager, move to a designer to plan and strategize, then move into Figma for design interaction and feedback before moving to the proposal and cross-functional collaboration for building.

A notable time I helped one of the designers on the team was when her project team was stuck on a problem. Nobody could see a path forward, so the team spent a solid month spinning their wheels. The designer came to me frustrated and concerned. I asked her if she had an idea of what the team needed to do and if she had taken the time to articulate what she thought was most important to the team. The answer was no, so together, we worked on a document that outlined a proposed focus for the team for the short term and three additional "phases" of the work the team could use to achieve their annual goal.

Of course, because Gem was a small and scrappy company, I did contribute some hands-on design work in addition to leading the team and working with my peers, the VP of Engineering, and the Head of Product.

Gem brand refresh

A significant experience from the first few months working at Gem was a brand refresh project we started in hopes of modernizing the company's outdated and unloved previous brand.

I brought in an outside contractor, Josh Williams of Facebook and Gowalla fame, to work with me and the executive team at Gem and envision what a more modern brand could look like for us. The intention was to partially overhaul Gem's brand, but rather add a layer of polish and principles that would better align with where the business was at.

Unfortunately, we lost the contractor shortly after the brand refresh project kicked off, but I was able to dedicate time to the effort fully myself. In a month, we were able to align on a direction and completely overhaul the Gem branding, collateral, and website. The resulting designs and brand refresh took Gem from looking like a hacked-together startup to a serious business.

I worked on many more projects during my time at Gem; if you're interested in hearing about any of them, reach out to me.

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