Principal Product Engineer

AwardSpring AI-Native Engineer

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 cracked, and you know it. You run fleets of agents, your token burn would make a CFO wince, you've built your own skills, plugins, and agents, and you've got real opinions about your multiplexer. You're at the bleeding edge of doing engineering the AI-native way, and you own the hardest, most ambiguous, highest-leverage problems we have. Just as important, you're someone the whole company learns from. You set the bar and pull everyone toward it. If you've been quietly building the future on your own time because no one around you could move at your speed, come do it here at full throttle, as the job.

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 problems end-to-end
• Push agentic development past where the rest of us are, and bring us with you
• Set the standard for how AwardSpring builds
• Make the calls that shape whole surfaces

Who You Are

• Roughly 8+ years, operating at the frontier of AI-native practice
• You build your own agents, skills, and plugins, run fleets, and burn tokens like it's your job (it is)
• Deep end-to-end judgment across product, design, and engineering
• 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.

A Note On Workspace

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