Lead Product Manager, AI Agents

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.

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.

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.

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.

• 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.

• 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.

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.

• 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.

• 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.