Who we are
AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.
About this 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
- ACTION
- Take initiative, be accountable, share what you know.
- DETERMINATION
- Simplify and improve, get past obstacles with creativity and persistence.
- HUMANITY
- Empathy and kindness in every interaction.
- IMPROVEMENT
- Grow daily, add value to clients and teammates.
A note on workspace
Hybrid, based in our West Loop / Fulton Market office in Chicago, roughly three days a week.
AI in our hiring
We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. Prefer a review without AI assistance? Email our hiring team at careers@awardspring.com to request it. It will not disadvantage you.
Equal Opportunity Employer
AwardSpring is an equal opportunity employer and hires without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. We're committed to an inclusive, harassment-free workplace.