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Principal Product Manager

LawnStarter - United States - In-office - posted 2026-09-04

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LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $150M in bookings. The company is expanding beyond lawn care to become a one-stop shop for home services across three brands (LawnStarter, Lawn Love, Home Gnome) on a shared platform. This is the most senior individual contributor product role with no direct reports. You'll serve as a peer to leaders in Operations, Data, Design, and Engineering, owning the Service Experience swim lane—everything after a customer books, for both customers and service professionals (Pros), increasingly powered by AI. You'll operate as both a strategic thought partner to leadership on how AI reshapes the service experience and a hands-on operator who ships with engineering, design, data, marketing, and operations at exceptional speed and quality. You're accountable for company-level metrics, not initiative-level ones. Key responsibilities include: owning the Service Experience product strategy and roadmap (marketplace trust, expectation-setting, Pro guidance, AI-assisted policies); building AI-powered support systems with rigorous evaluation frameworks (golden datasets, automated judges, regression detection); driving two company-level metrics (Contribution LTV and brand-promise metrics); and developing the vision and proof of concept for how AI transforms the customer and Pro experience beyond support. Core problems to solve: making AI support provably good and scaling it to resolve 50%+ of inquiries with high satisfaction; keeping promises on both sides by managing expectations and fairly arbitrating conflicts at scale; improving Contribution LTV by 10% year-over-year with defensible attribution; and deciding what AI does to the whole experience, not just support. Success in year one means: 50%+ of support inquiries resolved by AI with high satisfaction, backed by a regression-blocking eval suite and Pro-side AI support live; Contribution LTV up 10% with clear attribution; brand-promise metrics hit; a working proof of concept and leadership-endorsed vision for AI-transformed customer and Pro experience; and leadership treating you as the standard-setter for shipping trustworthy AI. This role is ultra AI-forward by design. You'll prototype with LLMs, write evaluation sets, read transcripts, and re-architect live systems yourself. You're expected to operate the way most PMs will operate in five years, with few layers between your judgment and what ships.

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