Design Leadership Framework
When I first joined Headway as the founding designer in 2022, the company had over 150 people, two PMs leading two seemingly functional products, and an engineering team of over 30 people.
Design was a delayed addition—a function that hadn’t yet been formally considered. If not for one well-respected PM advocating for the importance of design hiring, I suspect it might be postponed even further. After all, the company had PMs and a few talented engineers who could create mocks in Figma, achieve remarkable business traction that satisfied customers, and keep the board excited.
Fast forward to today, three years later, our design team has grown from one to 15 members, spanning product design, content design, UX research, and creative/brand. Despite multiple organizational changes, the team has grown steadily and delivered tremendous business and user impact throughout the entire user journey—from the first touchpoint at the top of the funnel to loyal customers using our product day to day.
Building and scaling a high-performing design team during the company’s growth from Series B to Series D has given me the opportunity to develop and evolve my approach to design leadership through various challenges.
My maternity leave has provided an excellent opportunity to reflect on this journey. While there’s much more to explore, I’ve gained valuable insights that are worth documenting. This series will examine the challenges I’ve faced, structured around four pillars—a framework I established for myself the evening before joining Headway.
Team: Build and scaling a high performing design team. It’s about having the right people and set them up for success in delivering the following 3 buckets. This is the most critical part of design leadership above everything.
Foundation: Establish the design system for effective execution. This is about building a shared language among designers and engineers that enhances velocity, consistency and quality - tailored to the company and product maturity.
Product: Leverage design as a key lever for better product engagement. It’s about creating meaningful experiences by deeply understanding customers and business and mastering of the craft.
Brand/Marketing: Position Design as a key lever to elevate external brand presence. This requires a clear definition and understanding of our ethos and delivering a compelling narrative through thoughtful storytelling.
Now let’s dive into each pillar. My hope is that this series can offer design leaders—both current and aspiring— and others a perspective on thinking through and solving these puzzles in a growing startup, potentially increasing the odds of their own success.