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Building our team culture & infrastructure

Process improvement

Archipelago gives commercial real estate insurance companies a place to clean up and enhance their property data. Owners and brokers can present insurers trustworthy information for better quotes.

From 2021 to 2023, design grew from 2 to 6 people spread across 3 cross-functional product teams. Along the way, everyone pitched in to create a cooperative and encouraging team culture. Here are some of my highlights.


I helped create a more thoughtful, efficient interview process. When I applied, it was 6-7 interviews stretched over a few weeks: phone screen, portfolio review, and a series of 1-on-1 meetings. We didn’t have meeting agendas or rubrics.

We shortened it to a phone screen, a panel interview, and 2 follow-up calls. For the panel interview, we had a simple agenda, a question bank, and a checklist for skills and culture fit. Later, when we were hiring for a new head of design, I organized a panel interview with the design team.


We initially didn’t do regular user research, but eventually we averaged 3 projects per quarter as a team in 2023.

To encourage our team to start projects, the head of design and I co-wrote training guides and research plan templates. These documents laid out expectations and included easy-to-follow checklists. We also started tracking research in our weekly planning meetings for accountability.

Another challenge was getting time with users, so we got help from customer-facing teams. Aside from sending us recorded customer calls, they did research with us.

Design feedback

As more people joined the design team, we started doing weekly critiques. This was dedicated time to:
  • Help each other work through problems.
  • Catch up on what other people were doing.
  • Practice public speaking in a safe environment.

Outside of crit, we did pair designing sessions and posted in Slack, so we didn’t have to wait for feedback.

Another source of feedback was design reviews with PMs, engineers, and stakeholders. We raised the quality of these meetings by helping PMs prepare, co-presenting, and debriefing afterwards. We also created colorful slide templates to get people excited about new features. 

Collaborating with other teams

Our design process was based on the principle that anyone can help with solutions, so we regularly met with PMs, engineers, and stakeholders throughout. They’ve seen research documents, user flows, wireframes, in-progress designs, and more. For engineers, we’ve held design reviews just for them and joined their sprint planning meetings.

We also hosted design office hours for anyone to ask for help, see what we’re working on, or just drop by. I created a signup sheet, set Slack reminders, and managed standing invites.

At one point, we got constructive feedback that design didn’t consistently do QA for new features. To fix that, we made it a design project requirement and created a checklist document. We also helped PMs prioritize bugs, negotiate scope, and write tickets.

File management

Finding projects in Figma was annoying, since we put everything in one product design folder and default thumbnails looked pretty similar.

Our solution was to split projects into folders and add color-coded thumbnails with large fonts to more obviously differentiate projects. I created Figma project templates to separate drafts, presentation assets, final designs, and UI specs.