LawnStarter: Senior Product Manager, Service Delivery
Headquarters: United States
URL: http://lawnstarter.com
About LawnStarter
LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $100M in annual bookings. We're expanding beyond lawn care to become the one-stop shop for all home services — operating across three brands (LawnStarter, Lawn Love, Home Gnome) on a single shared platform.
About Service Delivery at LawnStarter
We make a promise on both sides of the marketplace: customers get a job done well, and Pros get paid fairly for doing it. Service delivery is everything that happens after a customer books — keeping that promise through completion, support, and the moments when things don't go to plan.
This is the hard part of running a marketplace: we broker work we can't directly see, between two parties whose interests sometimes collide. Get it right and people stay for years. Get it wrong and you lose customers, Pros, or both. Trust is the product — and increasingly, the systems that protect it are AI-powered.
The Role
This is a broad Senior PM role on the quality, trust, and communication side of service delivery — setting the right expectations on both sides, steering Pros to deliver great work, resolving conflicting interests fairly, and making our AI-powered support genuinely good. You'll work on live, high-scale systems with a mandate to make them better.
Service delivery is a big area with more than one PM in it. You'll work alongside them; your center of gravity is the trust between both sides of the marketplace.
What makes this role different:
- It's a real area of impact, not a single feature. You'll shape strategy, policy, and the systems behind a whole slice of the post-booking experience — not optimize one screen.
- It's inherently two-sided. You work for customers and Pros at once, and you're often the one arbitrating between them. Pleasing one side at the other's expense is failure.
- AI is a core tool, not a side project. Support and outreach already run on AI. You'll push how far that goes — and build the evals that prove it's good before we trust it with more.
Problems to Solve
- Getting expectations right before the work ever starts. Most service failures aren't bad work — they're mismatched expectations. You'll make sure what's promised to the Pro matches what the customer actually expects, and that Pros are steered toward delivering great work.
- Arbitrating genuinely competing interests. You'll build the policies and the (increasingly AI-assisted) decision systems that resolve conflicts fairly and consistently at scale — and make the judgment call yourself when there's no clean answer.
- Making AI trustworthy enough to do more — which means evals. You'll own the eval systems — golden datasets, automated judges, regression detection, human-review sampling — that define what "good" means for an open-ended conversation, gate every change, and catch quality drift.
- Messaging that connects both sides — and quietly protects the marketplace. You'll keep communication easy for the legitimate 99% while spotting the patterns that quietly cost us customers, Pros, and revenue.
What Success Looks Like (Year 1)
- Expectations match on both sides: Pros know exactly what each job requires, customers get what they expected, and fewer jobs go sideways from misalignment.
- Competing interests resolve faster and more fairly: A clearer resolution model with measurable consistency.
- AI is provably good, and does more: An eval suite gates AI changes so no quality regression ships unseen, with higher resolution on customer support plus a first version of Pro-side AI support live.
- Messaging connects and protects: Measurable improvement in messaging reliability and engagement, plus working moderation that catches off-platform leakage and conflict early.
Who You Are
- AI-native: You use AI daily and have real intuition for how to measure whether an AI experience is actually good. You have built or owned evals.
- Comfortable making two-sided calls: You can hold both the customer's and the Pro's interest in your head at once and are willing to make the call when they conflict.
- You design for the right outcome up front: You prefer to get expectations right at the start rather than grading work after the fact.
- A marketplace systems thinker: You see service delivery as a system of incentives, policies, and feedback loops.
- Data-informed: You live in the numbers (CSAT, resolution rate, eval scores, churn, deflection) and know when to make a judgment call.
- Technically fluent: You partner with engineers on how AI and messaging systems work and give real feedback on design tradeoffs.
This Role Is NOT
- A support PM role: This is not about managing a ticket queue or a help center.
- The internal-AI role: This role is about AI in the user-facing service-delivery experience, not internal tooling.
- A greenfield 0→1 role: You will improve and re-architect systems that are already live and serving hundreds of thousands of people.
- A single-audience role: You must be comfortable serving and arbitrating between both customers and Pros.
Benefits
- Base salary: $140,000 - $185,000
- Equity: We want you invested in the long-term outcome.
- Healthcare: Medical, dental, and vision.
- Fully remote: Work from anywhere in the US.
- Flexible PTO: We focus on results.
LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. We comply with applicable state and local laws governing nondiscrimination in employment.
To apply: https://weworkremotely.com/remote-jobs/lawnstarter-senior-product-manager-service-delivery