Staff Product Designer

About the Role

You're a designer who's genuinely cracked. Deep craft, and you're at the bleeding edge of building the AI-native way: fleets of agents, your own skills and plugins, token burn to match, shipping production-quality design up and down the stack. You own our hardest, most ambiguous surface work, and the whole company learns craft and AI-native build from you. If you've been quietly building the future on your own time because your last shop only wanted mockups, come set the bar here.

How We Work

We're an AI-native product team. Nearly 100% of the code in our product is AI-generated, and every IC (engineer, PM, designer) ships features end-to-end with agentic tooling. The lines between disciplines are intentionally blurred: PMs ship code, engineers make product calls, designers prototype in production. We hire for fluency in agentic development, not time in any one stack. If you've been building this way on nights and weekends because your day job won't let you (rigid stack, no token budget, "that's not how we do things here"), this is the place where it's the actual job.

What You'll Do

• Own our hardest, most ambiguous surfaces end-to-end
• Push agentic design-and-build past where the rest of us are
• Set the craft and build standard for AwardSpring
• Make the calls that shape whole product surfaces

Who You Are

• Roughly 8+ years of design, operating at the AI-native frontier
• You build your own agents, skills, and plugins, run fleets, and burn tokens like it's the job
• Deep craft and end-to-end judgment across design and code
• People learn from you

What We Give You

• Top-tier AI tooling with unlimited token budgets
• Day-one access to the latest models as they ship
• A mature, multi-tenant production codebase with real users and real stakes
• Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave

Our Values

• Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.
• Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.
• Take pride in the process. Fast is the standard and thoughtfulness is non-negotiable. Eyes on the work you control, not the scoreboard.
• Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.

Workspace

Hybrid, based in our West Loop / Fulton Market office in Chicago, roughly three days a week.