By 2009, Grubhub was expanding into new cities, the product was getting more complex, and the marketing surface area had outgrown what any single designer could absorb without something slipping. The work quality wasn't degrading — but coverage was getting thin. Thinly spread attention is how design debt accumulates without anyone noticing until it's structural.

From 2009 to 2012, the team grew from just me to roughly ten people. From 2012 through the Seamless merger, another five or so. The question at each stage wasn't whether to hire — it was how to structure what we were building so it didn't become a pile of headcount with no connective tissue.

Fast-paced startup environments don't wait for you to figure out the org before handing you the next problem. I was making structural decisions while the ground was moving.

The first hire was deliberate: a UX designer who could also code. Our internal tools were multiplying and handoff friction at that stage cost more than it was worth. Front-end fluency in a designer meant fewer translation errors between design and engineering — early proof that design-as-code thinking matters even before you have a formal design system.

Every early hire shapes the culture that follows. I was hiring for aptitude and judgment, not just portfolio. Craftsmanship and curiosity over credentials.

As the team grew, a clear split emerged between product work and brand/marketing work. Keeping them under one umbrella was creating priority conflicts — a designer mid-flow on a product problem would get pulled onto a campaign deadline, and neither got the focus it deserved. I split into two branches — UX/Product Design and Brand/Marketing Design — each with different rhythms, different stakeholders, different quality metrics.

After that, hires followed actual gaps, not an org chart theory:

A second UX designer as product complexity grew:
Additional Product Designers to keep pace with our expanding product lines.
A part-time copywriter, because copy was shaping the brand as much as visual design was, and it was being written by whoever had bandwidth
A full-time user researcher — this one changed the quality of product decisions more than any other single hire
A visual designer with product sensibility, to keep the two branches speaking the same aesthetic language
The copywriter went full-time as marketing output scaled
A Head of Brand Design to run the marketing side — which freed me to focus on what actually needed my attention: keeping product and brand design aligned at the strategic level.

Pod structure. Designers were embedded in product pods, each aligned to a specific area of the product. This made designers genuine members of their cross-functional teams rather than external contributors who showed up to take a brief. As verticals became more distinct, roles narrowed — one UX designer and one visual designer on mobile, another pair on internal tools.

Cross-team cohesion. Pod structure creates efficiency and silos in equal measure. To address the silos, we ran regular lunch-and-learns between product and marketing designers — not formal presentations, just open show-and-tell. The goal was shared aesthetic vocabulary and the kind of familiarity that makes critique honest instead of careful.

Design critiques. Structured around improving work, not approving it. Whatever came out of critique was a prompt to consider, not a directive. Critique as command creates defensive designers. Critique as conversation creates better ones. This distinction — between a culture of feedback and a culture of approval — is one of the things I kept consistent as the team grew.

Resource allocation and prioritization. With two branches running simultaneously, I was constantly making trade-offs — who works on what, what gets deprioritized, when to escalate. The operational work of running a design org is unglamorous. It's also the thing that determines whether the team can do good work at all.

The design system. It grew alongside the team, not ahead of it. By the time we hit scale, the system held more than UI components and color specs — it included brand tenets and design principles, the layer that explains why decisions looked and felt the way they did. That's what keeps a design system from becoming a component library people quietly work around when it's inconvenient. It was also the foundation that made unifying two distinct design systems after the Seamless merger achievable at all.

The merger brought together two design teams with different processes, different brand systems, and different assumptions about how work got done. I co-led the design integration alongside the Head of UX — managing the unified team of 15, including researchers, designers, and copywriters.

The challenge wasn't technical. It was getting two groups of people, who had both been doing things a certain way for good reasons, to agree on a single path forward without losing the best of either. Alignment across cross-functional partners, clear communication about what was changing and why, and a lot of ambiguity that needed to resolve into something workable.

The design work produced during Grubhub's highest-growth years tracked alongside a 20% lift across conversion rate, repeat order rate, and cart size. The brand held its character through rapid expansion into new markets.

None of that happens without building the team right first — the hiring, the structure, the processes, the culture of high-quality design that makes good individual output possible in the first place.

A design org isn't just a collection of designers. It's a system. And systems, like products, need to be designed.