Staff Product Manager

AwardSpring; Chicago (IL); Hybrid; USD 175,000 - 245,000; Full time

Benefits offered by this job

Equity grant

Job summary

AwardSpring is seeking a Staff Product Manager in Chicago to lead AI-native product strategy at scale. You will own high-leverage bets, orchestrate fleets of agents, and set the standard for how we build and ship product across discovery, prototyping, and delivery.

You are a senior product leader with 8+ years’ experience, strong customer intuition, and a track record of autonomous decision-making. Join a fast-moving team with equity and a focus on impactful outcomes.

Qualifications

• 8+ years of product experience at the AI-native frontier.
• Orchestrate agents from discovery through delivery; build own workflows.
• Deep customer and product judgment; operate autonomously.
• Mentor others in product craft and decision-making.

Responsibilities

• Own our most ambiguous, highest-leverage product bets end-to-end.
• Push agentic product work past where the rest of us are.
• Set the standard for how AwardSpring does product.
• Make the calls that shape whole surfaces.

Skills

AI-native PM

Agent orchestration

Customer judgment

Autonomous leadership

Job description

Careers

Staff Product Manager

• Full-Time
• Chicago, IL
• Product Management

$175,000 - $245,000 / year

Includes an equity grant. We want you invested in what we're building.

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 product leader who builds. Deep customer intuition, years of hard-won judgment, and you're at the bleeding edge of doing PM the AI-native way, running fleets of agents across discovery, prototyping, and delivery, with the token burn to match. You own our most ambiguous, highest-leverage product bets, and the whole company learns product craft from you. If you've been dragging your org into the future on your own time, come set the pace 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 most ambiguous, highest-leverage product bets end-to-end
• Push agentic product work past where the rest of us are
• Set the standard for how AwardSpring does product
• Make the calls that shape whole surfaces

Who you are

• Roughly 8+ years in product, operating at the AI-native frontier
• You orchestrate agents from discovery through delivery, build your own workflows and skills, and burn tokens like it's the job
• Deep customer and product judgment, fully autonomous
• People learn product 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.

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.