Who we are

AwardSpring is an established and growing SaaS company that partners with colleges and foundations to help them award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again - between donors, students, and the institutions in the middle. We serve hundreds of institutions across the US and Canada with a small, focused team operating on a mature, multi-tenant platform.

About this role

AI-native development changed engineering first, but it's changing design just as fast. The line between a Figma file and a shipped feature is collapsing - and we want designers who are already shipping on the production side of that line. If you've used AI prototyping tools to ship real interfaces, or you've been frustrated that your work too often dies in handoff, this role is what you've been waiting for.

This is an individual contributor role on a small product team. You'll work directly with engineering and product on the same surface, ship into production, and report to the CTO.

How we work

AwardSpring is an AI-native product team. Nearly 100% of the code in our product is AI-generated. Every IC on this team - engineer, PM, designer, builder - ships features end-to-end in our codebase using agentic tooling. The line between traditional disciplines is intentionally blurred: PMs ship code, engineers make product calls, designers prototype in production. We hire for fluency in agentic development, not for time spent in any specific stack. If you've used Claude Code, Cursor, or comparable tools to ship real software at production quality, you already speak our language.

What you'll do

• Ship UX, UI, and interaction work end-to-end across our products. Three months in, we should be able to point to things that exist because you built them
• Prototype in code (via agentic tooling), not just in Figma - designs that ship are designs that work in the real codebase
• Own the visual and interaction system for the surfaces you touch
• Push back when product framings are weak; propose tighter alternatives
• Stay close to users; let what you observe shape what you ship

Who you are

• You've used Claude Code, Cursor, AI prototyping tools, or comparable agentic tools to ship real product work — not just mocks. We'll walk through what you built
• 3+ years shipping product design work that made it to production
• A portfolio that shows interaction, system, and craft thinking - not just visuals
• Strong opinions about what "good" looks like — design decisions and product decisions both
• Stack-agnostic; comfortable in unfamiliar codebases
• Comfortable presenting work to customers, executives, and peers

What we give you

• Top-of-market AI tooling: Claude Max, Cursor, GitHub Copilot, and whatever ships next - your call, our budget
• Unlimited token budgets. We don't ration the thing that makes you 10x
• Direct line to the latest models the day they release
• A mature, multi-tenant production codebase - real users, real stakes, real environments to ship in to
• Health, dental, vision, 401(k) match, unlimited PTO, paid parental leave

Our Values

• ACTION - When in doubt, spring into action. Be accountable. Teach what you've learned.
• DETERMINATION - Simplify and improve everything you touch. Expect obstacles. Be creative and relentless in your effort to overcome them.
• HUMANITY - Show empathy and kindness to everyone you interact with.
• IMPROVEMENT - Work hard every day to grow your knowledge and capabilities. Strive to become invaluable to clients and peers.

A note on workspace

We are Chicago-based with an office in West Loop / Fulton Market. This is a hybrid role for Chicago-area candidates; in-office presence is part of the job, with the specific schedule set with your manager.

AI in our hiring

We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. If you'd prefer your application be reviewed without AI assistance, note it in your cover letter — it won't disadvantage you.

Equal Opportunity Employer

AwardSpring is dedicated to building a diverse and inclusive workforce. AwardSpring is an equal opportunity employer and hires without regard for race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. We are committed to an environment free from harassment or discrimination.