Staff AI Engineer

SpotOn


Job Location:

Chicago, IL - USA

Monthly Salary: $ 210 - 280
Posted on: 6 days ago
Vacancies: 1 Vacancy

Department:

Engineering

Job Summary

About SpotOn

Were not just building restaurant tech were 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.

  • Named the #1 Restaurant POS by G2 (Fall 2025) based on ratings from real users

  • Rated the top-rated point-of-sale (POS) for restaurants bars retail and small businesses by Capterra users

  • Awarded Great Places to Work and Built Ins Best Workplaces for multiple years running

We move fast care hard and fight for independent restaurant operators to do what they love and love doing it. If youre 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.

Were 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. Youve 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. Youve seen what works in production and youre 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 dont manage the team. You drive the architecture build the hardest parts and set the technical standard.

The Role: Technical Lead Not Manager

This isnt 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 dont 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:

  • Automated PR Review - A risk-tiered AI review pipeline where AI handles first-pass review on every PR with an escalation framework you design that determines when human review is mandatory (payment logic PCI-scoped code compliance paths) versus when AI approval is sufficient. You define the criteria. You tune the thresholds. You prove it works.

  • Android and API Test Automation - A fully automated test harness for our Android-native POS and KDS products: virtual device provisioning test execution teardown AI-assisted failure analysis - replacing multi-day manual QA cycles with sub-30-minute automated runs.

  • AI Agent Swarms - A multi-agent pipeline that takes a PRD and produces a tested reviewed pull request for tier 1-3 engineering work (nits bugs small features). You design the agent orchestration - planner coder tester reviewer - and the blast-radius controls that keep it safe in fintech.

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 isnt 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:

  • 5 years building developer tools infrastructure or platform engineering systems - you understand how engineering orgs actually work at scale not just how AI demos work

  • 2 years working deeply with LLMs and AI agents in production - not side projects not hackathons. Production systems handling real code real reviews or real task automation. You can speak to failure modes cost optimization prompt engineering patterns and model selection trade-offs from experience.

  • Designed and operated AI-assisted code generation or review systems serving 50 engineers or 30 repositories. You know the difference between cool demo and trusted by the team.

  • Built multi-agent or agentic workflows - task decomposition agent specialization orchestration error recovery. Youve worked with Claude Code OpenAI Assistants LangGraph CrewAI AutoGen or custom agent frameworks at a level where you can articulate why you chose one approach over another.

  • Hands-on with AI coding tools daily - Claude Code Cursor GitHub Copilot Windsurf Codeium - you dont just use them you push their limits. You know where they excel and where they hallucinate. You have a personal workflow that makes you measurably faster and you can teach it.

Required domain expertise (at least two of three):

  • Fintech / payments / regulated industry - you understand what PCI-DSS SOX or HIPAA compliance means for code review and deployment. You know why just let the AI merge it isnt an option for payment logic.

  • Mobile / Android testing automation - Espresso UI Automator or AI-native tools (Drizz mabl testRigor). Experience with emulator farms device provisioning and CI-integrated test pipelines.

  • Multi-agent system architecture - youve built systems where multiple AI agents collaborate on decomposed tasks with coordination protocols fallback strategies and human-in-the-loop checkpoints.

Who You Are

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

  • You already write 50% of your code with AI assistance and youve measured the impact on your own velocity. You have opinions on which models are best for which tasks and you update those opinions monthly as the landscape shifts.

  • Youve built things with agents that most engineers think arent possible yet. Youre 6-12 months ahead of the mainstream in your personal practice and you have the shipped systems to prove it.

  • You prototype in hours not days. You can go from I have an idea for how to automate X to a working POC before end of day. You refine ruthlessly after.

  • You context-switch across backend mobile tooling and AI/ML systems without losing depth. You dont need to be an Android expert but you need to be dangerous enough to architect the test harness and evaluate the output.

  • You communicate technical progress in business terms. You know that we reduced median PR review time by 47% lands better with a CTO than we fine-tuned our prompt chain. You build dashboards not just systems.

  • Youre an evangelist not a gatekeeper. You get energy from showing other engineers how to work with AI. You dont hoard knowledge - you build systems that make the whole org better.

  • You have a healthy skepticism forged by real experience. Youve seen AI fail in production. Youve dealt with hallucinated code flaky agent workflows and false-positive reviews. That experience makes your guardrails better not your enthusiasm less.

What You Wont Be Doing

  • Building product features for restaurants (thats the rest of the org)

  • Pure ML/AI research without production deployment

  • Maintaining legacy systems or writing JIRA tickets all day

  • People management - youre a pure IC on a small senior fast-moving squad. You write more code than anyone on the team.

Tech Environment

  • Languages: Kotlin (Android) Go TypeScript Python

  • Mobile: Android-native POS applications on dedicated hardware

  • Infrastructure: AWS GitHub CI/CD (GitHub Actions)

  • AI Stack: Youll have significant influence on tool selection - bring your opinions

  • Team tooling: Jira Slack Figma standard SpotOn eng stack

Why Join Us

At SpotOn youll 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:

  • Our base pay range is $210000 -$290000 for this role

  • Please note the salary range listed is just one component of a competitive compensation package which includes a company stock plan

  • Offers will be reflective of the candidates location and experience.

Benefits:

At SpotOn we put people above everything else. Were known for our innovative software and technology solutions but we stand out because of the hard-working humans behind the tech. We cant take care of our clients without taking care of our employees first and thats why we invest in you with a competitive benefits package which includes:

  • Medical Dental and Vision Insurance

  • 401k with company match

  • RSUs

  • Paid vacation 10 company holidays sick time and volunteer time off

  • Employee Resource Groups to build community and inclusion at work

  • Monthly cell phone and internet stipend

  • Tuition reimbursement for up to $2000 per calendar year to assist with your professional development

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 (@). If something seems suspicious please contact us at .

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.


Required Experience:

Staff IC

About SpotOnWere not just building restaurant tech were 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 ...