Associate Product Engineer

AwardSpring; Chicago (IL); Hybrid; USD 85,000 - 110,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

401(k) match

Unlimited PTO

Paid parental leave

Job summary

AwardSpring, a growing SaaS company serving colleges, universities, and foundations across the US and Canada, is seeking an Associate Product Engineer in Chicago. You’ll join an AI-native product team building end-to-end features with agentic tooling.

You’ll learn fast, ship real code with guidance from senior engineers, and own well-scoped pieces early. This full-time role offers a hybrid work model from our West Loop office and access to top-tier AI tooling.

Qualifications

• Shipped something real with agentic tools at work, school, or on your own time.
• 0–2 years in
• You learn fast and want to be great, not comfortable.
• You'd rather ship and iterate than wait for perfect instructions.

Responsibilities

• Ship well-scoped features end-to-end with agentic tooling and senior review.
• Learn the codebase and our agent workflows fast.
• Push on specs that don't make sense.
• Stay close to how customers actually use what you build.

Skills

Agentic tooling experience

Fast learner

Shipping features

Tools

Claude Code

Cursor

AI tooling

Job description

Careers

Associate Product Engineer

• Full-Time
• Chicago, IL
• Product Engineering

$85,000 - $110,000 / 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

This is where you start building the AI-native way for real. You've shipped something with Claude Code, Cursor, or a comparable tool, a side project, a hackathon, a scrappy internal thing, and you want to go deeper than your current role allows. We care more about how fast you learn than how long your resume is. You'll work next to senior builders who'll show you how we ship, and own well-scoped pieces end-to-end early.

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 well-scoped features end-to-end with agentic tooling and senior review
• Learn the codebase and our agent workflows fast
• Push on specs that don't make sense
• Stay close to how customers actually use what you build

Who you are

• You've shipped something real with agentic tools, at work, at school, or on your own time
• 0–2 years in
• You learn fast and want to be great, not comfortable
• You'd rather ship and iterate than wait for perfect instructions

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.