By 2009, Grubhub was expanding into new cities, the product was more complex, and the marketing surface area had grown beyond what any single designer could absorb without something slipping. The work quality wasn't degrading — but coverage was getting thin, and 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, we added 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.

The first hire was deliberate: a UX designer who could also code, because our internal tools were multiplying and handoff friction at that stage was more hindrance than help. Every early hire shapes the culture that follows. I was hiring for aptitude and judgment, not just portfolio.

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.

Hires after that followed actual gaps, not an org chart theory. A second UX designer. 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, which changed the quality of product decisions meaningfully. A visual designer with product sensibility to keep the two branches from drifting aesthetically. The copywriter went full-time as marketing output scaled.

When I was promoted to Creative Director, I hired a Head of Brand Design to run the marketing side, which freed me to focus on what mattered most: keeping product design and brand design speaking the same language. Grubhub had a personality — playful, direct, built around the actual experience of ordering food — and that had to come through in the product, not just campaigns.

Pod structure. Designers were embedded in tech pods, each aligned to a specific product area. This made designers genuine members of their product teams rather than external contributors. As verticals became more distinct, roles narrowed: one UX designer and visual designer on mobile (I'd built the first version myself in 2007 — handing that off was its own milestone), another pair on internal tools.

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

Design critiques. Regular sessions structured around improving work, not approving it. Whatever came out of critique was a prompt to consider, not a mandate. Critique as command creates defensive designers. Critique as conversation creates better ones.

The design system. It grew alongside the team, not ahead of it. By scale, the system held more than UI components and color specs — it included brand tenets and principles, the layer that explains why design decisions looked and felt the way they did. That's what keeps a design system from becoming a component library people quietly ignore when it's inconvenient.

The work produced during Grubhub's highest-growth years tracked alongside a 20% lift in conversion, repeat orders, and cart size. The brand held its character through rapid expansion into new markets. The design system survived the Seamless merger and became the foundation for unifying two distinct brand and product systems.

None of that happens without building the team right first.