The Wing
Website + iOS app
Role
Director of Product Design
Responsibilities
Dept. Leadership, Design Ops, Hiring, Manager / IC Hybrid (End-to-End)
Team
X-functional team of thirty-two
Design team of four
Before you read about this design work, I think it's important to call out that The Wing’s culture was toxic, damaging, and entirely unconscionable. Myself and the majority of my colleagues — most specifically those working in the spaces — were negatively impacted by this environment, and spoke up about unjust treatment only to have our feedback be disregarded. I in no way support the company's leadership, decision-making, and actions. Feel free to read more about just how bad it was here, and more importantly, donate to space staff reparations. 
New Hire Task #1: Embrace the chaos
Jumping in
I came to The Wing in 2018 as their first product designer, joining one product manager and two engineering peers.
In full startup fashion, the digital products that existed — a member and admin website — broke constantly. Design and code were spaghetti, there was no native app, and agile processes supporting the business’s rapid growth were lacking.
One year later, this group scaled to a cross-functional team of 32 people, released an iOS app for members, and shipped numerous features that boosted key acquisition and engagement metrics. Not bad for one trip around the sun.
One team, one dream: us at the end of 2019.
Farewell, dear agencies
Prior to coming on board, The Wing relied heavily on the dev and design talents of external agencies The Couch and Prolific Interactive. I needed to simultaneously hire a design team while onboarding and inheriting a long history of decisions and debt.
Building clear scaffolding for design and insights was integral to providing role clarity, fair performance evaluation, and standardized hiring assessment.
Building a design team
A major focus of my first six months was to build out the company’s product design and research function. I spent over 40 hours doing phone screens, wrote job descriptions, and developed a scaffolding for career pathing to ensure everyone we hired would understand how they fit into the org.
Once we’d grown, I worked with the team to create design rituals, optimize handover, critique, and QA, and build an open, trusting design culture. Additionally, as a people manager of four, I conducted weekly 1:1’s, quarterly goal-setting, and bi-annual performance reviews, always advocating for my team’s health, happiness, and upward trajectory.
Job descriptions were vetted and actively avoided language or expectations that might deter applications from marginalized groups.
Each week, the team met in a ‘Design Jam’ to discuss milestones and catch up.
Symbols! Symbols everywhere!
Investing in a cohesive system
In an effort to streamline both existing and new aspects of our product ecosystem, I helped prioritize and path out ongoing work on the design foundation holding it together.
This meant prioritizing, refining, and implementing core components in shared libraries and Storybook, ultimately delivering a more consistent front-end to users and speeding up our internal workflows.
The team refined our vertical and horizontal rhythm across the product.
Components were prioritized and built out in Storybook.
We gave the public-facing site a fresh Contentful re-do, resulting in a 63% increase in clicks to apply.
Overhauling our entire acquisition funnel
When I joined, the full path from consideration to conversion was built on old Meteor technology and lacked a CMS. I led the complete redesign of our public website, as well as oversaw a re-launch of our application and confirmation flows.
These efforts not only reduced friction for prospective Wing members, but enabled other teams in the company to update the site without relying on an engineer to deploy.
We enabled prospects to configure membership packages via a fast, lightweight experience.
Color combinations were vetted to meet AA contrast standards.
We released new, lower friction application and confirmation flows.
The three pillars of strategy informing our feature roadmap.
Workshopping the future
The product design team was constantly setting an example for new ways of thinking across the business. We led several exercises with peers, third parties, and even investors, engaging stakeholders in the design process and generating early ideas and insight that shaped our roadmap.
Design sprints included rapid prototyping and testing with members.
The discovery phase of a project: caffeine, stickies, and sketchpads.
Snapshots of our member job board, a feature released to help members hire and support one another’s ventures.
Unlocking new value exchanges
After the foundational digital product was released, the team focused their efforts on releasing features that drove retention, engagement, and connection within The Wing community.
In just a year, we released direct and group messaging, a member job board, interest-based groups, and experimented with member matching to spark conversation and bring people together.
We formed and tested hypotheses around engagement loops.
Groups and matching helped members connect over shared interests.
Stakeholders and colleagues could see what we were up to via weekly email roundups.
Sharing process, promoting transparency
As a technically-savvy team in a non-tech company, we also had a unique opportunity to inspire and teach other teams about our process.
I helped with this by building cross-functional initiatives for all Wing design (brand, marketing, and product), advocating for demos in our main library space, and deploying a weekly newsletter update with highlights from the team.
Cross-departmental, all-design initiatives.
Demos showcased work-in-progress, and inspired other teams to take the stage.