[Hiring] Lead Product Manager, AI Agents @LawnStarter

Role Description

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.
• Knowing when to hand off, and doing it well.
• When the customer's agent is the one asking.
• Evals and guardrails for two audiences.

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.
• 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.

Qualifications

• 6+ years of product management experience, including at least 3 years launching AI products to customers (internal or external).
• An AI builder who has shipped to real users.
• The owner of quality: you write evals yourself.
• Fluent in agents and tool use.
• A strategist who prioritizes with data.
• A systems thinker.

Requirements

• This Role Is NOT a people-management role.
• A research or ML-platform seat.
• For AI skeptics.
• A strategy-only seat.
• A role with foundations already built.
• Low-stakes.

Benefits

• Base salary: $170,000 to $225,000.
• Healthcare: Medical, dental, and vision.
• Location: Fully remote (US).
• PTO: Flexible. We focus on results. Take what you need.