Product Engineer

AwardSpring Job Opportunity

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 ship complex, high-value features end-to-end, with agentic tooling as your primary interface to the codebase. You make the technical calls on what you own, push back when a spec is wrong, and stay close to the customers who depend on it. You don't wait for groomed tickets, you take a problem and go.

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

• Ship complex features end-to-end across our products
• Drive the technical decisions for the systems you own
• Push back on weak specs and propose the better version
• Keep a direct line to customers and peers

Who You Are

• 3+ years shipping production software, now doing it with Claude Code, Cursor, or comparable tools
• Comfortable in unfamiliar code
• Strong opinions about quality in product and craft
• Can hold your own with customers and executives

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.

A Note On Workspace

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