Hiring: Principal Product Manager Company: LawnStarter Location: Chicago, IL Job Posted Time: 2026-09-10 10:41:59 Employment Type: Remote Target Skills & Keywords : LLM, Product Strategy About the job Required Skills: •This is the most senior individual contributor seat in Product, with no direct reports. You'll work as a peer to the leaders of Ops, Data, Design, and Engineering. •What Makes This Role Different •Thought partner, not order-taker. Leadership wants your view on where AI takes the service experience, and expects you to change their minds sometimes •Speed and quality together. Small team, peers in engineering, design, data, marketing, and ops who move fast, and few layers between your judgment and what ships •Ultra AI-forward is the point. We want someone already operating the way most PMs will operate in five years •Strategy and hands. You still prototype with LLMs, write eval sets, read transcripts, and re-architect live systems yourself Qualifications: •The Service Experience swim lane's product strategy and roadmap: marketplace trust after booking, including setting the right expectations on both sides, steering Pros toward great work, and the increasingly AI-assisted policies that arbitrate conflicts •AI-powered support for customers and Pros, including the eval systems that gate every change (golden datasets, automated judges, regression detection, human-review sampling) •Two company-level numbers: Contribution LTV (profit per customer over their lifetime) and the brand-promise metrics •The vision and proof of concept for how AI transforms the customer and Pro experience, not just support •The bar for product: standards for shipping trustworthy AI, influencing Senior PMs by showing what great looks like, and being the person leadership calls for the hardest two-sided judgment calls •Making AI support provably good, then letting it do a lot more. •Keeping the promise on both sides. •Making every customer more profitable. •Trust isn't a soft metric here: customers who get what they were promised stay for years, and conflicts resolved fairly cost less to serve. You'll own Contribution LTV, targeting +10% year over year. The hard part is knowing which lever moves it (retention, cost to serve, fewer make-goods) and proving the attribution, not just asserting it. •Deciding what AI does to the whole experience, not just support. Compensation: •$185,000 - $230,000 / year •Flexible work environment (work from home / hybrid options) •Equity: We want our product managers to benefit from significant company growth, so equity is a meaningful part of how we structure PM compensation Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!