Senior Product Manager

AwardSpring; Chicago (IL); Hybrid; USD 135,000 - 175,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

401(k) match

Unlimited PTO

Paid parental leave

Job summary

AwardSpring in Chicago is seeking a Senior Product Manager who will own significant product areas end-to-end, from discovery to production. You will run agent workflows and make autonomous priority calls while mentoring newer builders.

The role emphasizes agentic tooling, direct customer interaction, and shipping with a small, focused team. Hybrid work from our West Loop office three days a week, with competitive compensation and comprehensive benefits.

Qualifications

• 5–8 years in product with serious customer time
• Experience shipping with agentic tooling
• Sharp, autonomous product judgment
• PM blending into building where you are

Responsibilities

• Own significant product areas end-to-end, discovery to production
• Run your own agent workflows to ship, not just to spec
• Make the priority and quality calls autonomously
• Mentor newer builders and raise the bar

Skills

Agentic tooling

Customer interaction

End-to-end ownership

Autonomous decision making

Tools

Agent workflows

Job description

Careers

Senior Product Manager

• Full-Time
• Chicago, IL
• Product Management

$135,000 - $175,000 / year

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 came up as a real PM, with years in front of customers and sharp product judgment, and you seized agentic tooling to start shipping the work yourself instead of handing off specs. You run your own agent workflows, own product areas end-to-end, and make the calls autonomously. If you've been building product this way outside a role that only ever wanted the spec, this is where it becomes the work.

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 significant product areas end-to-end, discovery to production
• Run your own agent workflows to ship, not just to spec
• Make the priority and quality calls autonomously
• Mentor newer builders and raise the bar

Who you are

• Roughly 5–8 years in product with serious customer time
• Fluent shipping with agentic tooling, and you've built your own workflows and skills
• Sharp, autonomous product judgment
• Probably already the PM blurring into building where you are

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.