Build the Product
Disclaimer: I’ve intentionally excluded specific features and product details, focusing instead on transferable practices that can be shared publicly.
When it comes to building products at startups, reality rarely matches the ideal. Sometimes we lack PMs on specific projects due to recent departures, sometimes newly formed teams have no engineering resources at all, and sometimes urgent legal requirements outweigh all other requests in the roadmap.
Building products involves constant tough tradeoffs, where competing priorities can easily pull the team away from delivering customer value. These options range from chasing growth numbers to meet ambitious company targets, concentrate resources in addressing unsized legal and compliance risks, or building fancy dashboards for leadership review. While each decision may seem reasonable in isolation, adding up overtime they pose a serious risk—especially when competitors are focused on creating real customer value nonstop.
As a design leader, I advocate for the unique value design brings to product and ensure the team crafts solutions that genuinely meet user needs. This is especially challenging in metrics-driven environments, where the focus on short-term growth and shipping velocity—while essential for startup success—can sometimes overshadow user-centricity and quality.
This article is not about case studies on individual features. Rather, I want to focus on how I approach and think about building organizational muscle that champions the user-first investments, craft and product quality in a startup environment. I want to dive into the the practices in three areas: Culture, Organizational positioning and Practices.
Culture of customer obsession with UX Research
Building organizational consensus around customer centricity is the single most important lever for driving intentional product development. While I believe every product team starts with the best intentions and wants to do right by their customers, somewhere along the way, things could slip. Simply imagine the scenarios where it takes two weeks just to schedule eight customer interviews, or having only the designer advocate for customer pain points that no one else see it first hand or resonates.
A key part of fostering a customer-obsessed culture is investing in UX Research. But it goes beyond simply having researchers speak with customers or encouraging all product makers to engage with users without clear purpose or agency.
At Headway, the research team creates the playbook and pipeline that empowers all product makers to engage directly with users. By fostering empathy through firsthand conversations and making customer insights easily accessible, we ensure user needs stay at the center of our work. To accelerate the feedback loop, we’ve built an active research panel of thousands of customers, ready to provide valuable input at a short notice.
New designers often tell me how impressed they are with Headway's customer-centric approach. This stands in stark contrast to their previous startup experiences, where talking to customers could be viewed as a bottleneck. Even coming from Meta's research-friendly environment, I rarely see product discussions with this level of nuance and insight. This is only possible because customer obsession is woven into everything we do, supported by the leadership cares, a team deeply invested in understanding customers and equipped with the right tools.
Organizational Position: 3 Legged Stool
I've witnessed stark differences in product strategy when designers are—or aren't—in the room during its development. To maximize the potential of the product-minded designers, it's crucial to secure their seats at the table through thoughtful organizational design.
While this might seem obvious in some companies, it’s the opposite in others. Aligning on design’s role within the organization—starting at the leadership level—is critical, and I consider that alignment should begin before joining a company, leaving the finer details of org structure for later.
At Headway, I ensure the three-legged stool model remains our foundation, regardless of how the organization evolves. Every designer is paired with dedicated PM and engineering partners, creating a balanced trio that fosters collaboration. Depending on team maturity, these trios adapt their working models to ensure effective partnerships.
The more context designers have, the stronger their thought partnership becomes, consistently leading to better solutions, creating a virtuous cycle. We’ll inevitably make wrong trade-offs, but a shared culture, goals and clear alignment on how we work together help the team stay the course and adjust when needed.
Design-led Product Practices
When the design team was small, each designer had their own way of working with cross-functional partners, and it was a lower priority for me to instrument team-level practices. Overtime, I noticed some designers bringing excellent practices that others could learn from. Meanwhile, whenever PMs or designers switched teams, they had to relearn how to work with new partners. This revealed a clear opportunity to implement shared practices that help socialize best practices and ensure effective XFN collaboration at scale.
There’re three activities where I found particularly helpful in help designers better contribute to product development.
Design Sprint
Design sprints are a powerful tool for aligning leadership on product direction and inspiring teams with future possibilities. While there are many frameworks available, we tailor them to fit our needs—ranging from quick sessions lasting a few hours to more in-depth explorations over two weeks—depending on the questions and context at hand.
At the start of each quarter, I align with product leadership to identify the most critical questions we want to explore and determine where a design sprint can add value. These sprints serve as an effective shared tool across all levels and functions, especially for leadership, who often take a longer-term view of problems.
We make it a priority to run at least one design sprint each quarter. Beyond generating valuable insights, these sprints act as a cultural touchpoint, bringing designers together for an intense, focused period of creativity and craft.
Design Kickoff
This is a practice where designers take the lead in kicking off the design phase with cross-functional (XFN) teams—a format introduced by design manager Jenna.
What I love about this approach is how it transforms lengthy product requirement documents into a dynamic, visual experience that sparks creativity. The designer presents the current solution (you’d be surprised how many XFN partners have limited visibility into what the product actually looks like) and facilitates a discussion to align on user problems, design principles, and possible future directions.
This practice not only gives designers valuable insight into how other functions perceive the problem, but more importantly, it helps XFN partners start thinking through a user lens. It sets the right mindset early on, enabling more thoughtful and user-centered evaluations of solutions as the project progresses.
Design 30/60/90 Spec
Our design specs use percentage markers to indicate fidelity levels and guide feedback. A 30% spec explores core concepts, a 60% spec details the main user flow, and a 90% spec covers all scenarios but pending content finalization. This structured approach helps the team better align timelines—engineers can begin backend work with a 30% spec while saving space for designers to take additional time to refine and polish the work.
Last not the least
Building products is a deep profession. There isn't a single framework or set of rules that leads to mastery. Yet this is precisely what makes the work fascinating—this is where taste and judgment come in.
Beyond implementing organizational practices, I believe it's crucial to stay close to the product, users, and craft as a design leader. Although I no longer do production-level design and research, I still participate in design sprints, talk to customers directly, collaborate on design solutions, and create design improvement proposals. These activities help me stay sharp, form clear perspectives, and continue pushing the team toward excellence.