Lead AI Product Manager, Conversational & Actions (Remote)

LawnStarter; Chicago (IL); Hybrid; USD 170,000 - 225,000; Full time

Job summary

LawnStarter is seeking its first core AI PM to own conversational AI and agent experiences for homeowners and Pros. You will drive the AI roadmap, shape how AI acts inside product flows, and ensure seamless handoffs to humans when needed.

You will collaborate with engineering, design, data, and customer service to deploy real AI actions that improve the LawnStarter marketplace, with a focus on measurable customer and Pro outcomes.

Qualifications

• 6+ years of product management experience on consumer-facing products.
• Experience shipping AI products to customers (internal or external).
• Ability to write evals and guardrails; decide when an AI experience is ready to ship.

Responsibilities

• Define the AI roadmap for consumer and Pro AI applications.
• Own customer AI chat and actions, including handoffs to human support.
• Lead AI chat inside the Pros App and other existing workflows.
• Design AI agents inside existing workflows and external agents integration.
• Shape customer-to-Pro messaging and bot handoffs with full context.
• Set guardrails and evaluation criteria for the AI experiences.

Skills

Product management

AI products

Chatbot / Conversational AI

Cross-functional leadership

Data-driven prioritization

Education

Bachelor's degree or equivalent

Tools

Agents and tools

Job description

LawnStarter is seeking its first core AI PM to own conversational AI and agent experiences for homeowners and Pros. You will drive the AI roadmap, shape how AI acts inside product flows, and ensure seamless handoffs to humans when needed.

You will collaborate with engineering, design, data, and customer service to deploy real AI actions that improve the LawnStarter marketplace, with a focus on measurable customer and Pro outcomes.