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SpotOn · Hiring

Staff AI Engineer

Chicago, ILHybridFull Time$210K – $280K • Offers Equity

About SpotOn

We’re not just building restaurant tech, we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sh*t about helping restaurants succeed.

We move fast, care hard, and fight for independent restaurant operators to do what they love, and love doing it. If you’re looking to make an impact with heart and hustle, SpotOn is the place for you.

(Remote Friendly)

About the Accelerate Team

The Accelerate team is a new 5-person engineering team with a singular mission: prove that AI-native engineering practices can fundamentally change how a fintech engineering org builds software - then make that the new standard. The team has direct VP sponsorship, mission & charter, and three defined projects with hard deadlines.

We're hiring a Staff/Principal IC who has already demonstrated AI-assisted engineering at scale. This is not an "AI-curious" role. You write code with AI every day. You've built agents that do real work. You have strong, experience-backed opinions on which models to use for what, where agents fail, and how to build guardrails that actually hold. You've seen what works in production and you're impatient to do it at scale.

You will be the most technically senior AI practitioner on this team - the person everyone looks to for "how do we actually build this." You don't manage the team. You drive the architecture, build the hardest parts, and set the technical standard.

The Role: Technical Lead, Not Manager

This isn't a "set up some CI/CD and plug in Copilot" role. You are the person who architects the systems that change how SpotOn engineers build software. You will:

Be the AI engineering technical authority. You set the technical standard for how AI is used in code generation, review, testing, and task automation. You don't just implement tools - you design the systems, workflows, and guardrails that make AI-assisted development safe, measurable, and scalable in a PCI-regulated payments environment. The team lead sets priorities; you set the technical direction.

Drive the architecture and implementation of three concurrent projects:

Evangelize by shipping, not by presenting. Your most persuasive argument is a working system, not a slide deck. You demo to engineering leads every two weeks with real metrics. You turn skeptics into adopters by showing them their own time savings.

Measure everything. You define the metrics framework: developer hours recovered, cycle time compression, quality ratios, cost per deployment. You report to the CTO monthly with quantified value delivered. If something isn't working, the data tells you before anyone else.

What We Require

This is a high bar intentionally. We need someone who has already done this, not someone who wants to learn.

Required experience:

Required domain expertise (at least two of three):

Who You Are

You are not "AI-interested." You are AI-obsessed in the productive sense:

What You Won't Be Doing

Tech Environment

Why Join Us?

At SpotOn, you’ll be part of a team that values diversity, creativity, and a shared mission to help small businesses succeed. Join us to build technology that makes a difference, work with talented peers, and contribute to a culture where your ideas and impact matter.

Compensation:

Benefits:

At SpotOn, we put people above everything else. We’re known for our innovative software and technology solutions, but we stand out because of the hard-working humans behind the tech. We can’t take care of our clients without taking care of our employees first, and that’s why we invest in you with a competitive benefits package which includes:

We will never ask candidates to pay fees, purchase equipment, or share sensitive personal or financial information during the hiring process. All legitimate communication from our recruiting team will come from an official company email address (@spoton.com). If something seems suspicious, please contact us at careers@spoton.com.

SpotOn is an equal employment opportunity employer. Qualified candidates are considered for employment without regard to race, religion, gender, gender identity, sexual orientation, national origin, age, military or veteran status, disability, or any other characteristic protected by applicable law.

Work authorization in the U.S. is required. Visa sponsorship is not available for this role.

SpotOn is an E-Verify company.

Interested in This Role?

Apply at SpotOn

You'll head to SpotOn's own careers page.