Lead Product Manager, AI Agents

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 star