Top Tech Jobs & Startup Jobs in Chicago, IL

Own the end-to-end consumer experience after first booking, including onboarding, discovery, property details, scheduling, reviews, cancellations, win-back, cross-sell, personalization, and AI-powered experiences. Set product vision and roadmap, collaborate with engineering, design, data, marketing, and operations, and deliver measurable improvements in retention, lifetime value, and satisfaction while balancing marketplace impacts on service Pros.

Lead the product strategy and execution for LawnStarter’s consumer and Pro AI agent experiences. Own conversational AI, agent actions, customer-to-Pro messaging, human handoffs, workflow integrations, external AI agent access, evaluations, and guardrails. Ship reliable AI capabilities that resolve issues, complete bookings and service changes, improve productivity, and increase retention. This individual contributor role requires cross-functional leadership across engineering, applied science, design, data, support, and operations.

Own and rebuild the consumer first-service experience across LawnStarter’s three brands, from marketing-site entry through signup, quoting, scheduling, checkout, and first booking. Define the product vision, design an AI-native and agentic experience, analyze funnel performance, prototype with customers, and ship improvements with engineering, design, operations, marketing, and data teams. Success includes increased conversion, more first-service bookings, and strong customer satisfaction.

Own the end-to-end consumer experience after first booking, including onboarding, discovery, scheduling, personalization, cross-sell, cancellations, and win-back. Set the product vision and roadmap, launch AI-powered experiences, improve retention and customer satisfaction, and balance customer outcomes with marketplace effects on Pros, pricing, and operations. This is a senior individual-contributor role requiring scaled B2C product experience, strong analytics, personalization expertise, and hands-on AI product development.