AI Product Engineer Jobs in Illinois
AI Product Engineer jobs in Illinois are actively sought across a competitive and growing market, with demand concentrated in enterprise software, financial technology, and healthcare technology sectors at levels from entry-level associate to senior principal engineer. Chicago leads hiring volume by a wide margin, with Champaign-Urbana and Naperville also generating consistent openings tied to major employers and research institutions. Companies like Morningstar, Zebra Technologies, and Allstate have lasting Illinois footprints and regularly hire ai product engineers, particularly in areas like LLM integration, MLOps, and product-facing AI feature development. Find a role that fits below and apply directly.
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About LawnStarter
LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $750M in bookings. We're expanding beyond lawn care to become the one-stop shop for home services: three brands (LawnStarter, Lawn Love, Home Gnome), one shared platform.
About Product at LawnStarter
Our BHAG: 1+ job per household, every year. Getting there means winning on four fronts at once: more customers, more Pros, excellent service for both sides, and an AI-run company that moves faster than its size should allow.
About AI Agents at LawnStarter
Our mission: power every AI experience. For homeowners and for Pros (the lawn care providers on our marketplace), conversational AI can do far more than answer questions. It can skip a service, reschedule a visit, or book a new one mid-conversation, even when the customer's own AI agent is the one talking. And it doesn't have to live only in a chat window: we're bringing agentic experiences into the workflows homeowners and Pros already use, so the product does the work for them wherever they are. You'll decide what that looks like for both sides, then ship it.
The Role
This is LawnStarter's first core AI PM role. You'll own our conversational AI and agent experiences for consumers and Pros: the chat, the actions it takes, the moment it hands off to a person, and how outside AI agents work with us. Beyond chat, you'll bring agentic experiences into existing consumer and Pro workflows, so AI takes action inside the product rather than alongside it.
As Lead PM, you're an individual contributor with Lead-level scope, reporting to the Sr. Director of Product. The AI experiences you power will often sit inside surfaces other PMs own, so you'll share goals with the Customer Experience lead, the First Service Experience lead, and the Pro Experience PM, and build with engineering, applied science, design, data, customer service, and operations.
What makes this role different:
- Fast, and at the center. Within a year, we expect AI to shape a meaningful share of how homeowners and Pros experience LawnStarter, and you’ll be at the center of making that happen. This role moves fast and rewards people who ship.
- You're the first. The evals, the guardrails, and the bar for "ready to ship" are yours to set.
- The AI takes real actions. It reschedules and skips services on a live marketplace. No sandbox.
- Two sides, one conversation. Everything you ship serves homeowners, Pros, or both, and an action for one changes the other's day.
What You'll Own
- The AI roadmap: Where consumer AI and Pro AI go next, and the order we build it in.
- Customer AI chat: Answering homeowners' questions and completing tasks, like skipping or rescheduling a service.
- AI chat in the Pros App: The AI experience Pros get inside the app they work from.
- Agents inside existing workflows: AI that acts within the consumer and Pro flows people already use, not just in a chat window.
- Customer-to-Pro messaging: How homeowners and Pros talk to each other.
- The handoff to human support: When the bot passes a conversation to a support agent.
- Outside AI agents: Letting a customer's own agent, such as ChatGPT or Claude, work with us on their behalf.
Problems to Solve
From answering questions to solving problems.
A chatbot that explains how to reschedule is useful. One that understands what the customer or Pro actually needs, recommends the right thing, and then does it for them is a different product, and a riskier one. Sometimes the best answer isn’t the action they asked for: a skip might be better as a reschedule, or a one-time booking better as a plan. You’ll decide which actions the AI takes on its own, which need confirmation, and what happens when it gets one wrong.
Knowing when to hand off, and doing it well.
Some conversations belong with a person. Which ones? And can the bot tell before the customer gets frustrated? When the handoff comes, the support agent should pick up with full context so the customer doesn't repeat themselves.
When the customer's agent is the one asking.
Sometimes the one talking to LawnStarter won't be a homeowner. It'll be their own AI agent, such as ChatGPT, asking about a service, booking one, or changing it. You'll work out what we let an outside agent do and how the customer stays in control.
Evals and guardrails for two audiences.
A good answer for a homeowner isn't a good answer for a Pro. You'll build the evals that tell us when an AI experience is good enough to ship and when its quality slips, plus the guardrails that keep it safe once it's live.
What Success Looks Like (Year 1)
- AI shaping the experience: AI experiences live for consumers and Pros, and shaping a meaningful share of how both sides interact with LawnStarter, measured by:
- Share of conversations resolved by AI without a human (resolution or containment rate)
- CSAT on AI conversations, for homeowners and Pros
- Action accuracy: errors on reschedules, skips, and bookings stay below a set bar
- Pros get more done because of AI: Pros spend less time on admin and coordination, and say AI makes them more productive.
- More customers stay because AI makes service better: Consumer and Pro retention rises, driven by AI that resolves problems faster and improves the service experience.
Requirements
Who You Are
Experience: 6+ years of product management, including at least 3 years launching AI products to customers (internal or external).
An AI builder who has shipped to real users. You've put AI products in front of real end users, whether in B2C, B2B, or B2B2C, and at least one was a chatbot or conversational AI running in production. You read transcripts to find where conversations break. If your AI work stopped at demos, prototypes, or a thin prompt wrapper that never met a real user, this isn't your role.
The owner of quality. You write evals yourself. You know when an AI experience is good enough to ship, and when its quality starts to slip. Would you rather someone else define what "good" means? Then you'll struggle here.
Fluent in agents and tool use. You understand what changes when an agent stops producing text and starts calling actions on real systems, and you design for the ways that goes wrong. PMs who treat AI as a feature bolted onto the side won't last here.
A strategist who prioritizes with data. You set priorities, say no with reasons, and back each call with evidence. If your roadmaps run on instinct alone, this is unlikely to be a good fit.
A systems thinker. You see a product change as one part of a larger system and think through its second- and third-order effects before you ship. Here, that system is a marketplace: a change for customers almost always touches Pros, pricing, and operations too. You plan for those effects in the spec, not after launch. Marketplace experience helps, but what matters most is that you instinctively ask, "What else does this change?" If you'd rather ship your piece and let other teams deal with what it changes, this isn't your role.
This Role Is NOT
- A people-management role. You're an individual contributor with no direct reports.
- A research or ML-platform seat. If your AI career has been research or platform work that never reached end users, this isn't the fit.
- For AI skeptics. If you see AI as an add-on rather than the product, you'll fight the job daily.
- A strategy-only seat. You'll write the evals and read the transcripts. Setting direction from a distance won't work here.
- A role with foundations already built. You'll build the evals, the guardrails, and how we decide an AI experience is ready, not inherit them. We're also lean and frugal, on a partly legacy stack.
-
Low-stakes. AI that reschedules or skips a service fails in front of customers and Pros, so the safety bar is high. And since your work lives inside surfaces other PMs own, you'll lead through influence.
Bachelor’s degree in business, analytics, engineering, design, or a related field, or equivalent practical experience, plus 6+ years of product management experience on consumer-facing products.
Benefits
- Equity: AI is how LawnStarter plans to move faster than its size, and this role decides how that shows up for customers and Pros. Equity means you share in what that builds.
- Base salary: $170,000 to $225,000
- Healthcare: Medical, dental, and vision
- Location: Fully remote (US). Evals, transcripts, and failure cases reward deep focus, and remote work protects it.
- PTO: Flexible. We focus on results. Take what you need.
LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. We comply with applicable state and local laws governing nondiscrimination in employment.
About LawnStarter
LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $750M in bookings. We're expanding beyond lawn care to become the one-stop shop for home services: three brands (LawnStarter, Lawn Love, Home Gnome), one shared platform.
About Product at LawnStarter
Our BHAG: 1+ job per household, every year. Getting there means winning on four fronts at once: more customers, more Pros, excellent service for both sides, and an AI-run company that moves faster than its size should allow.
About AI Agents at LawnStarter
Our mission: power every AI experience. For homeowners and for Pros (the lawn care providers on our marketplace), conversational AI can do far more than answer questions. It can skip a service, reschedule a visit, or book a new one mid-conversation, even when the customer's own AI agent is the one talking. And it doesn't have to live only in a chat window: we're bringing agentic experiences into the workflows homeowners and Pros already use, so the product does the work for them wherever they are. You'll decide what that looks like for both sides, then ship it.
The Role
This is LawnStarter's first core AI PM role. You'll own our conversational AI and agent experiences for consumers and Pros: the chat, the actions it takes, the moment it hands off to a person, and how outside AI agents work with us. Beyond chat, you'll bring agentic experiences into existing consumer and Pro workflows, so AI takes action inside the product rather than alongside it.
As Lead PM, you're an individual contributor with Lead-level scope, reporting to the Sr. Director of Product. The AI experiences you power will often sit inside surfaces other PMs own, so you'll share goals with the Customer Experience lead, the First Service Experience lead, and the Pro Experience PM, and build with engineering, applied science, design, data, customer service, and operations.
What makes this role different:
- Fast, and at the center. Within a year, we expect AI to shape a meaningful share of how homeowners and Pros experience LawnStarter, and you’ll be at the center of making that happen. This role moves fast and rewards people who ship.
- You're the first. The evals, the guardrails, and the bar for "ready to ship" are yours to set.
- The AI takes real actions. It reschedules and skips services on a live marketplace. No sandbox.
- Two sides, one conversation. Everything you ship serves homeowners, Pros, or both, and an action for one changes the other's day.
What You'll Own
- The AI roadmap: Where consumer AI and Pro AI go next, and the order we build it in.
- Customer AI chat: Answering homeowners' questions and completing tasks, like skipping or rescheduling a service.
- AI chat in the Pros App: The AI experience Pros get inside the app they work from.
- Agents inside existing workflows: AI that acts within the consumer and Pro flows people already use, not just in a chat window.
- Customer-to-Pro messaging: How homeowners and Pros talk to each other.
- The handoff to human support: When the bot passes a conversation to a support agent.
- Outside AI agents: Letting a customer's own agent, such as ChatGPT or Claude, work with us on their behalf.
Problems to Solve
From answering questions to solving problems.
A chatbot that explains how to reschedule is useful. One that understands what the customer or Pro actually needs, recommends the right thing, and then does it for them is a different product, and a riskier one. Sometimes the best answer isn’t the action they asked for: a skip might be better as a reschedule, or a one-time booking better as a plan. You’ll decide which actions the AI takes on its own, which need confirmation, and what happens when it gets one wrong.
Knowing when to hand off, and doing it well.
Some conversations belong with a person. Which ones? And can the bot tell before the customer gets frustrated? When the handoff comes, the support agent should pick up with full context so the customer doesn't repeat themselves.
When the customer's agent is the one asking.
Sometimes the one talking to LawnStarter won't be a homeowner. It'll be their own AI agent, such as ChatGPT, asking about a service, booking one, or changing it. You'll work out what we let an outside agent do and how the customer stays in control.
Evals and guardrails for two audiences.
A good answer for a homeowner isn't a good answer for a Pro. You'll build the evals that tell us when an AI experience is good enough to ship and when its quality slips, plus the guardrails that keep it safe once it's live.
What Success Looks Like (Year 1)
- AI shaping the experience: AI experiences live for consumers and Pros, and shaping a meaningful share of how both sides interact with LawnStarter, measured by:
- Share of conversations resolved by AI without a human (resolution or containment rate)
- CSAT on AI conversations, for homeowners and Pros
- Action accuracy: errors on reschedules, skips, and bookings stay below a set bar
- Pros get more done because of AI: Pros spend less time on admin and coordination, and say AI makes them more productive.
- More customers stay because AI makes service better: Consumer and Pro retention rises, driven by AI that resolves problems faster and improves the service experience.
Requirements
Who You Are
Experience: 6+ years of product management, including at least 3 years launching AI products to customers (internal or external).
An AI builder who has shipped to real users. You've put AI products in front of real end users, whether in B2C, B2B, or B2B2C, and at least one was a chatbot or conversational AI running in production. You read transcripts to find where conversations break. If your AI work stopped at demos, prototypes, or a thin prompt wrapper that never met a real user, this isn't your role.
The owner of quality. You write evals yourself. You know when an AI experience is good enough to ship, and when its quality starts to slip. Would you rather someone else define what "good" means? Then you'll struggle here.
Fluent in agents and tool use. You understand what changes when an agent stops producing text and starts calling actions on real systems, and you design for the ways that goes wrong. PMs who treat AI as a feature bolted onto the side won't last here.
A strategist who prioritizes with data. You set priorities, say no with reasons, and back each call with evidence. If your roadmaps run on instinct alone, this is unlikely to be a good fit.
A systems thinker. You see a product change as one part of a larger system and think through its second- and third-order effects before you ship. Here, that system is a marketplace: a change for customers almost always touches Pros, pricing, and operations too. You plan for those effects in the spec, not after launch. Marketplace experience helps, but what matters most is that you instinctively ask, "What else does this change?" If you'd rather ship your piece and let other teams deal with what it changes, this isn't your role.
This Role Is NOT
- A people-management role. You're an individual contributor with no direct reports.
- A research or ML-platform seat. If your AI career has been research or platform work that never reached end users, this isn't the fit.
- For AI skeptics. If you see AI as an add-on rather than the product, you'll fight the job daily.
- A strategy-only seat. You'll write the evals and read the transcripts. Setting direction from a distance won't work here.
- A role with foundations already built. You'll build the evals, the guardrails, and how we decide an AI experience is ready, not inherit them. We're also lean and frugal, on a partly legacy stack.
-
Low-stakes. AI that reschedules or skips a service fails in front of customers and Pros, so the safety bar is high. And since your work lives inside surfaces other PMs own, you'll lead through influence.
Bachelor’s degree in business, analytics, engineering, design, or a related field, or equivalent practical experience, plus 6+ years of product management experience on consumer-facing products.
Benefits
- Equity: AI is how LawnStarter plans to move faster than its size, and this role decides how that shows up for customers and Pros. Equity means you share in what that builds.
- Base salary: $170,000 to $225,000
- Healthcare: Medical, dental, and vision
- Location: Fully remote (US). Evals, transcripts, and failure cases reward deep focus, and remote work protects it.
- PTO: Flexible. We focus on results. Take what you need.
LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. We comply with applicable state and local laws governing nondiscrimination in employment.
See All 40 AI Product Engineer Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
Find AI Product Engineer JobsAI Product Engineer Jobs by City in Illinois
Where Illinois roles are concentrated, by current openings.
AI Product Engineer Job Market in Illinois
A snapshot from current Illinois openings, updated as new roles post.
Who's Hiring
Top Industries Hiring
- Banking & Financial Services
- Consulting & Professional Services
What Illinois Employers Look For
The qualifications that appear most often in AI product engineer jobs across Illinois.
- Bachelor's or master's degree in computer science, AI, or a closely related engineering field
- Hands-on experience building and shipping AI-powered features in a production environment
- Proficiency with machine learning frameworks such as PyTorch, TensorFlow, or scikit-learn
- Demonstrated ability to translate business requirements into AI product specifications and roadmaps
- Experience collaborating with cross-functional teams including data scientists, designers, and product managers
- Familiarity with cloud platforms such as AWS, Azure, or Google Cloud for deploying AI systems
AI Product Engineer Jobs in Illinois: Frequently Asked Questions
How do you become a ai product engineer in Illinois?
Most Illinois employers expect a bachelor's degree in computer science, software engineering, or a related technical field as the foundation, with a master's degree preferred at larger firms like those headquartered in Chicago's Loop or along the North Shore tech corridor. There is no state-issued license required for this role in Illinois. Building a portfolio of shipped AI features or contributing to open-source ML projects is the most reliable way to demonstrate readiness to Illinois hiring teams.
Which companies hire ai product engineers in Illinois?
Employers hiring ai product engineers in Illinois right now include TransUnion, Boston Consulting, and Lenovo, based on current listings on Migrate Mate as of November 2026. Illinois's concentration of enterprise software firms, insurance carriers, and fintech companies makes it one of the more consistent hiring markets for this role outside the coastal tech hubs.
Which Illinois cities have the most ai product engineer jobs?
Chicago, Illinois, and Lisle are the Illinois cities with the most ai product engineer openings, driven primarily by Chicago's dense concentration of enterprise technology, financial services, and healthcare organizations, while suburban markets like Naperville benefit from large corporate campuses and regional headquarters that run dedicated product engineering teams.
Are there remote ai product engineer jobs in Illinois?
Yes, and more than most fields. About 86% of ai product engineer openings tied to Illinois are remote or hybrid as of November 2026, reflecting how much of this work centers on code, model development, and product collaboration that translates well to distributed teams. The most remote-friendly subspecialties are LLM integration, prompt engineering, and AI product strategy work that does not require on-site infrastructure access.
How can I get hired as a ai product engineer in Illinois with little or no experience?
The most realistic entry path is moving from an adjacent role, such as software engineer, data analyst, or ML research assistant, into an AI product function once you have shipped at least one AI-adjacent feature or project. Large Illinois employers including Allstate and Zebra Technologies run associate and rotational engineering programs that accept candidates without dedicated AI product experience. Building a demonstrable portfolio, completing a recognized certification in machine learning or product management, and targeting roles titled 'associate AI engineer' or 'AI product associate' will open the most doors in the Illinois market.
Where can I find and apply to ai product engineer jobs in Illinois?
You can find and apply to ai product engineer jobs in Illinois on Migrate Mate, which lists current Illinois openings updated regularly. Search the listings to find roles that match your experience level and preferred location, then apply directly to the ones that fit.
See All 40 AI Product Engineer Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
Find AI Product Engineer Jobs