Build the Design Team
If you need a bit more context, start with My Leadership Framework
Joined as founding designer, I had the opportunity to grow alongside the company, leading the entire design function and managing ICs and managers. The design team evolved from a narrowly defined discipline focused on product into a fully functioning team, with UX research function added in late 2022 and a creative team added in 2023.
Through this journey, I’ve come to learn that building a successful team isn’t just about hiring high-performing talents—it’s about how you structure and operationalize the team to unlock its full potential. While there’s no universal playbook for solving complex challenges, I have refined a few frameworks and practices that helps me navigate difficult decisions and ambiguities effectively.
Defining Design Discipline
To start, let me define a design team. I see broader design disciplines is to deliver business and user value through creation of the product and brand experiences with deep understanding of customers. This encompasses three key functions: Product design, Creative/marketing and UX research. Each function plays a distinct role in shaping the experiences with further specializations.
Product Design: This function focuses on designing intuitive product experiences. It includes product designers, content designers, and design system designers.
Creative: This function brings the brand to life across various channels and touch points. It includes brand designers, copywriters, Creative Ops and other specialists.
UX Research: This function uncovers user needs, behaviors and pain points to inform design and product decisions. It includes qualitative and quantitative researchers.
It's important to note that while these functions—Product Design, UX research, and Creative—are essential for a cohesive design team and common in larger companies, they aren't all necessary for early-stage startups. These functions also shouldn't receive equal priority. One of my most critical alignments with leadership was determining how to sequence the team's growth to match the company's business needs, which I'll discuss below.
Grow a design team
Team Structure
Rather than proposing headcount reactively—which often leads to rushed hiring and delays—I focused on anticipating where the company and product would be in the next 6-12 months. This allowed me to organize the design team to support that vision while staying ahead of our growth curve.
To illustrate this progression, I use the analogy of evolving from a solo performer to a band, and finally to an orchestra.
The evolution of the design team
Solo performer: in the early stage, 1-2 design generalists handle a few selectively aspects of design, focuses on versatility. At this stage, I’ve focused on building a nimble team with primary focus on accelerating the product development with design from 0-1.
Band: As the product and company expand, the design team grows into a small group with specialized roles, such as UXR and content design. At this stage, I’ve focused on establish a design function to look across all products to make the entire user experience great.
Orchestra: In a more mature stage, the design team functions like a well-coordinated orchestra with broader coverage. This enables the team to tackle more complex storytelling and nuanced design practices.
It took about a year to transition from phase 1 to phase 2 with some setbacks due to mismatched hires. Moving from phase 2 to phase 3 took another 1.5 years, during which I established a relatively stable team structure and operational frameworks that allowed us to scale and iterate effectively.
Build Specialized Functions
Most startup leaders treat design as a single discipline, with product designers expected to handle everything - marketing materials, product design, and user research
While it’s possible to find a designer who can handle all aspects, this approach presents major challenges in hiring, retention as well as overall work quality.
Instead, I prefer a strength-based model where having designers focusing primarily on 1-2 core areas of expertise while building capacity overtime through outsourcing and hiring for specialists.
The key question is when to bring a specialization in-house to build the function systematically. It varies a lot based on company dynamics and product domain. But there are three indicators I look for to determine the right timing at Headway:
Cost effectiveness: is there enough work to justify a full-time role? If the workload has reached a critical mass, hiring in-house may be more cost-effective than relying on external contractors or treating the role as a secondary responsibility for existing team members.
Long-term need: is the need for this function ongoing and central to the company & product strategy or is the increasing demand tied to a one-off initiative?
Stakeholder readiness: are there empowered stakeholders in place who can help integrate and leverage the function?
I learned firsthand how timing affects a new function's success. When I introduced UX research (UXR) before having a fully empowered product team, we could only serve tactical needs rather than playing a strategic role. The function only gained real momentum after a Chief Product Officer (CPO) joined, bringing the insights into exec team’s decision-making process.
The Creative function, however, launched at a much better time. The company was actively tackling brand positioning challenges, rebuilding its marketing function, and hiring its first Head of Growth Marketing. This timing allowed the creative team to deliver immediate impact through tactical support for ongoing marketing efforts and lasting impact by overhauling the brand foundation with marketing leaders.
Hire the Best Possible Talents
With a clear candidate profile in mind, the next challenge is attracting the best possible talent to the company. While this proved to be the most challenging task during my first year at Headway, it became the most rewarding when we got the right people in place.
The core challenge of startup hiring lies in the tension between needing highly competent talent while lacking the brand recognition and competitive compensation packages to attract them. This became even more difficult during the industry downturn in late 2022.
Finding our second designer took nearly 5 months, and subsequent hires have averaged 3-4 months from search to close. While I leveraged many techniques and resources, there's really one key principle standout — going the extra mile at every step to make the opportunity feel special and personalized for those highly competent candidates.
The interview process is a two-way conversation, and selling the opportunity begins long before the offer stage. I partnered with our talent team to evaluate each step of the hiring funnel and integrate compelling selling points throughout.
Sourcing stage: For promising candidates, I schedule a sell call with product demos before starting the formal interview process.
Interview stage: I designed two interactive design exercises—app critique and whiteboarding—to understand candidates' thought processes in solving design challenges while giving them hands-on experience with our work. The questions candidates ask and things they poke around reveal the depth of their thinking.
Offer delivery: Rather than entirely delegating to recruiters, I personally deliver each offer with a pitch highlighting what impressed us during interviews and how I envision the candidate contributing to Headway's critical initiatives with those strengths.
Closing stage: This phase focuses on addressing any lingering concerns through personal connection. When I was choosing between Headway and other options, my manager sent a personal message and invited me on a walk around Green Lake—a defining moment that helped me feel comfortable taking the risk. Ultimately, I believe personal connections are what convince mission-driven and competent talents through the finish line after evaluating the core elements on the paper. I strive to create similar genuine connections by introducing candidates to team members, inviting them to visit our office and have in-depth conversations with the team and myself.
Although much of this process involves selling the opportunity, true success depends on giving candidates an authentic view of the work while openly discussing both the team's requirements and understanding the candidate's own needs.
Many candidates don't truly know what they want, even if they seem certain at first. That's why it's crucial to not sugarcoating anything because startup work is demanding. I’ve experienced several promising candidates turn down the opportunity. The outcome served both the candidate and team well—it's best to have people join who are in the right mindset and life stage to take on the opportunity and commit to the work.
These thoughtful interactions have helped us attract top talent, even when competing against well-known design-led companies. Throughout multiple organizational changes as the company grew, the design team maintained its stability and reputation for high team caliber.
Operationalize the Team
Design Operation
As the team grew from 1 to 15 and expanded into multiple functions, I evolved our operations several times. Here's the framework I developed for organizing different types of meetings, inspired by the Config talk on team rituals.
Despite having regular meetings scheduled, team members reported feeling disconnected and lacking mentorship in earlier 2024. I also observed that engagement levels during our meetings had declined.
To address this, I began by redesigning our most frequent meetings, working with a small committee of designers (Jenna and Yiwei) with me in reshaping our team rituals.
1 - Revitalize Design Crit
We enhanced our critique sessions with structured, productive discussions. Each designer completes a template with project context to frame the discussion and assigns a note-taker.
We introduced sticky notes for attendees to share feedback beyond the presenter's specific questions, creating a more inclusive environment for quieter team members. This approach increased engagement from 1-2 sessions to 5-6 sessions weekly and has proven most effective in facilitating a more engaging discussion and elevating our design quality.
2 - Evolve Team Weekly
Our previous team meetings followed a PPP (progress, plan, and problem) format—participants spent five minutes silently reading before discussing items marked with microphone emojis.
While this approach worked well at the leadership level, our design team needed more human connection and creative outlets. Working with a designer, we transformed this into two components that enhanced personal expression and creativity while maintaining accountability and improving visibility between team members.
Monday asynchronous standup: Designers share their top three priorities for the week.
Friday wrap-up meeting: I provide leadership updates while designers report on their top three items using traffic light status, discuss roadblocks, share weekend plans, and express their week creatively through visuals—from emojis to memes, work samples, or AI-generated graphics.
3 - Design Pairing
Inspired by pair programming in software development, we created design jams—intimate forums where designers tackle design challenges together in Figma.
These organic jam sessions evolved into a quarterly design pairing program, matching 2-3 designers with shared context for regular collaboration. This practice has yielded stronger solutions while fostering deeper team connections.
Leadership Engagement
Another important aspect of team operations is leadership engagement. Finding effective ways to keep leaders informed about team health is crucial - not just celebrating successes, but also identifying potential issues before they become serious problems.
After experimenting with various formats to convey updates meaningfully rather than performatively, I found our most effective approach to be executive check-in every 6 weeks, which functions like mini board meetings.
We review a snapshot of team health, covering positive areas, negative issues, and concerning trends that could become problems without intervention. We then discuss the progress of major design initiatives. My manager noted this was "the right altitude that he hopes to do more with others."
This approach has proven extremely valuable in several ways:
It builds trust with leadership by demonstrating the team knows what it doing and eliminating surprises down the road.
It allows us to address challenges early by giving executives proper context—many issues can be resolved simply through awareness.
It creates opportunities for design leaders to gain direct executive context
Conclusion
Building a team from scratch with limited managerial experience has been challenging. The right choices weren't always obvious—and by the time they became obvious, it was often too late. Team building became the area where I did my most original work over the past few years. A lot of iteration happened and mistakes are corrected along the way, sometimes under great stress especially when it comes to hiring and firing decisions. But this is also the most rewarding part to see a diverse and competent team who’s able to deliver the work far beyond myself.