Senior Software Engineer - Python/Typescript Chicago, IL

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.

• 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 In’s 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 you’re looking to make an impact with heart and hustle, SpotOn is the place for you.

About This Role

Our operations, sales, and customer support teams run on workflows that were designed for humans — and many of them should no longer be. Manual handoffs, repetitive processes, slow queues, and duct-taped integrations are costing us speed, accuracy, and money. We're hiring a Senior AI Engineer to fix that.

Your job is simple to describe and hard to do: find the inefficiencies across our business operations and replace them with AI-driven systems that are faster, smarter, and scalable. You'll work directly with ops, sales, and support stakeholders, understand their pain points firsthand, and build the automation that eliminates them. One week you might be streamlining a customer support triage workflow; the next, you're building an agentic pipeline that handles a multi-step process currently requiring a team of people and days of turnaround.

This is a high-autonomy, high-impact IC role. You won't have someone writing detailed specs for you. You'll get a business problem, dig into it, architect a solution, and ship it. We need someone who's been deep in AI-assisted development for years — not just prompting models, but building real orchestration layers, integrating agentic workflows into production, and producing code that's disciplined and reviewable. We are not interested in AI-generated slop.

The Role: Builder, Not Bureaucrat

You are the person who walks into a room, hears someone describe a painful manual process, and walks out knowing exactly how to automate it. You will:

Own business automation end-to-end. You partner directly with operations, sales, and customer support teams to identify workflow bottlenecks and manual processes ripe for automation. You don't wait for a product manager to write you a spec. You discover the problem, scope the solution, build it, deploy it, and measure the impact.

Design and ship AI-driven systems that replace manual labor. These aren't chatbot wrappers. You're building agentic workflows and orchestration layers that handle complex, multi-step business processes autonomously — with the guardrails and error handling required for production use in a fintech environment. You build systems that people trust because they work reliably, not because someone mandated adoption.

Measure everything. You define the metrics that matter: hours recovered, error rates reduced, cycle times compressed, operational throughput gained. You report impact in business terms. "We automated X and saved Y hours per week" is the language you speak. If something isn't delivering value, the data tells you before anyone else.

Evangelize by shipping, not by presenting. Your most persuasive argument is a working system, not a slide deck. You turn skeptics into believers by showing them their own time savings. You build systems that make the whole ops org better, not just your team.

What We Require

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

Required Experience

• 7+ years of professional software engineering experience — you understand how engineering and business systems actually work at scale, not just how AI demos work.
• Strong proficiency in Python and TypeScript/JavaScript — you can build production systems in both. Not scripts. Not notebooks. Production.
• Full-stack capability spanning backend services, APIs, and frontend interfaces. You can build the automation pipeline and the dashboard that shows it's working.
• 1–2+ years working deeply with LLMs and AI agents in production — not side projects, not hackathons. Real systems handling real workflows. You can speak to failure modes, cost optimization, prompt engineering patterns, and model selection trade-offs from experience.
• Built multi-agent or agentic workflows — task decomposition, agent specialization, orchestration, error recovery. You've worked with Claude Code, 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, or similar. You don't just use them, you push their limits. You have a personal workflow that makes you measurably faster and you can teach it to others.
• Comfort working directly with non-technical stakeholders. You can sit with a support lead, understand their workflow, and translate it into a technical solution without needing a translator.

Nice to Have

• Familiarity with Salesforce platform development (Apex, Lightning, APIs) — we have significant Salesforce surface area and someone who can automate within it is extremely valuable.
• Experience building custom AI orchestration layers or multi-agent systems for business process automation.
• Background in CI/CD pipeline design and cloud infrastructure (AWS, GCP, or Azure).
• Prior experience in ops automation, business process reengineering, or internal tooling at a fast-growing company.

Who You Are

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

• You already write the majority of your code with AI assistance and you've measured the impact on your own velocity. You have opinions on which models are best for which tasks and you update those opinions as the landscape shifts.
• You prototype in hours, not days. You can go from "I think we can automate this" to a working POC before end of day. You refine ruthlessly after.
• You see a manual business process and your brain immediately starts decomposing it into automatable steps. You can't help it.
• You communicate technical progress in business terms. You know that "we eliminated 40 hours per week of manual triage" lands better with leadership than "we built a multi-agent orchestration pipeline." You build dashboards, not just systems.
• You have a healthy skepticism forged by real experience. You've seen AI fail in production. You've dealt with hallucinated outputs, flaky agent workflows, and systems that looked great in demo but broke under real load. That experience makes your guardrails better, not your enthusiasm less.

What You Won't Be Doing

• Building product features for restaurants (that's the rest of the org)
• Pure ML/AI research without production deployment
• Waiting for someone to write you a detailed spec before you start building
• People management — you're a pure IC who ships. You write more code than you write emails.

Tech Environment

• Languages: Python, TypeScript
• Infrastructure: AWS, GitHub, CI/CD (GitHub Actions)
• Business Systems: Salesforce, internal ops tooling
• AI Stack: You'll have significant influence on tool selection — bring your opinions
• Team tooling: Jira, Slack, standard SpotOn eng stack

How to Stand Out

Tell us about a time you looked at a manual business process, saw the waste, and built something that made it disappear. We want to hear what you automated, how you built it, and what the impact was. Bonus points if AI agents were a core part of the solution — and you can tell us where they worked, where they broke, and what you learned.

Compensation:

• Our base pay range starts at $160,000 -$200,000/year 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 candidate’s location and experience.

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:

• 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 $2,000 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 (spoton.com). If something seems suspicious, please contact us at View email address on click.appcast.io.

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.