• 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. • You'll work alongside other PMs; your center of gravity is the trust between both sides of the marketplace. • You'll shape strategy, policy, and the systems behind a whole slice of the post-booking experience — not optimize one screen. • You'll build the policies and the decision systems that resolve these fairly and consistently at scale — and make the judgment call yourself when there's no clean answer. • 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.

• The PM team: Lead, coach, and multiply three already-strong PMs — and hire more as we grow. • Prioritization: Own the growth/retention/profitability tradeoffs on one shared roadmap — what gets built, what waits, what we kill. • Multi-service strategy: Turn one proven vertical into a repeatable playbook across services, designing for customers and Pros as one system. • Agent-native direction: Own how AI and agents show up in what we build — for our team, our customers, and our Pros. • Cross-functional partnership: Be the product leader the rest of the company trusts to make the right calls.

• Lead the PM organization, with all product managers reporting and designers reporting to you. • Own and communicate the product roadmap, timelines, and resource allocation across 7–8 cross-functional pods. • Oversee all product lines • Serve as the primary product representative to senior leadership • Partner closely with incoming engineering directors and engineering managers to align roadmaps and delivery. • Write roadmaps, design docs, and PRDs directly—our leaders are makers, not just managers. • Drive AI adoption across the PM team: every PM should have a proper AI workflow, and no PRD should be written from scratch. • Push back on leadership, when you believe the roadmap needs to change, backed by data and clear reasoning. • Champion bottom-up product development in addition to executing top-down priorities. • AI is embedded in everything we do. The right candidate will be genuinely excited to talk about their personal and professional AI setup at length.

Role Description This is LawnStarter's first Director of Product Management — the leader between the VP of Product and a team of three PMs (and the hires that follow). The mandate is simple to state and hard to do: ship value across growth, retention, and profitability by building a great product for customers and Pros. Concretely, that means taking us from one profitable-at-scale vertical to two, setting the path from two to n, while still aggressively improving our core lawn service. What Makes This Role Different - You build the layer, not inherit it. This is a brand-new layer between the VP and the PMs. - It's a marketplace, so the obvious answer is usually wrong. Almost every decision has second-order effects across customers, Pros, and the business. - You multiply a strong team — this isn't a turnaround. The PMs are already good. - Strategic bets and patient optimization, both. What You'll Own - The PM team: Lead, coach, and multiply three already-strong PMs — and hire more as we grow. - Prioritization: Own the growth/retention/profitability tradeoffs on one shared roadmap. - Multi-service strategy: Turn one proven vertical into a repeatable playbook across services. - Agent-native direction: Own how AI and agents show up in what we build. - Cross-functional partnership: Be the product leader the rest of the company trusts to make the right calls. Problems to Solve - Abstracting one product into a multi-service platform. - Prioritizing across three goals with one capacity. - Building for the agent era. What Success Looks Like (Year 1) - The team ships at a higher ceiling. - Wins in all three goals: measurable progress on growth, retention, and profitability. - Second vertical on track: Pool cleaning progressing toward profitable-at-scale. - A stronger brand through quality: measurable improvement in the quality of our core service. - An agent-native vision: a clear roadmap for winning in an agent-driven world. Qualifications - AI-native and agent-curious. - A player-coach who multiplies talent. - A systems thinker. - A brutal prioritizer. - A great cross-functional partner. - Obsessive about scoping and user experience. This Role Is NOT - A pure people-management role. - A solo-IC role. - A turnaround. - A fit for an AI skeptic. - A role with a finished playbook. Benefits - Equity: A significant leadership equity package. - Base salary: 200k - 230k. - Healthcare: Medical, dental, and vision. - Fully remote: Work from anywhere in the US. - Flexible PTO: We focus on results. Take what you need.