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.

• Customer Discovery. Immerse yourself in customer workflows, constraints, motivations, and pains. Capture revealed preferences and weigh them against stated preferences and internal vision. Use this to maintain strong intuitions and data-backed positions on where the product should go. • Roadmap Alignment. Synthesize customer learnings, the existing roadmap, sales requests, and engineering priorities into a sequenced plan that different teams can execute against. • Outcomes Ownership. Own outcomes from vaguely identified needs to solutions with real-world impact. Define what to build and why. Identify, surface, and reconcile tradeoffs. Push through cross-functional blockers. Be the CEO of whatever initiative you’re involved with. • Measurable Outputs. Introduce metrics wherever helpful. Own tracking and iterating based on them. • Sales Enablement. Review personalized sales collaterals. Join prospective calls. Work closely with BD to help close deals. • Institutional-Grade Product Readiness. Bake real institutional requirements — control, permissioning, auditability, performance guarantees, operational clarity, risk, SLAs, procurement — into product decisions from day one. • Cross-Functional Facilitation. Find blockers throughout tech, sales, and marketing and proactively help unblock them.

• Own the vision and roadmap for Employee Training product • Integrate AI capabilities into product • Accelerate team's discovery and delivery cycles with AI • Define clear, prioritized work from ambiguous problems • Collaborate across Engineering, Design, Data, and Marketing

Role Description 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. - Arbitrating genuinely competing interests. A customer wants a date the Pro can't commit to. The grass is long enough to need a different price tier than booked. - Making AI trustworthy enough to do more — which means evals. You'll own the eval systems that define what "good" means for an open-ended conversation. - Messaging that connects both sides — and quietly protects the marketplace. What Success Looks Like (Year 1): - Expectations match on both sides: Pros know exactly what each job requires, customers get what they expected. - 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. - Messaging connects and protects: Measurable improvement in messaging reliability and engagement. Qualifications - AI-native: You use AI daily in your own work and have real intuition for how to measure whether an AI experience is actually good. - Comfortable making two-sided calls: You can hold both the customer's and the Pro's interest in your head at once. - You design for the right outcome up front: You're not satisfied 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 that matter here — CSAT, resolution rate, eval scores, churn, deflection. - Technically fluent: You partner with engineers on how AI and messaging systems work. Requirements - This Role Is NOT a support PM role. - The internal-AI role. - A greenfield 0→1 role. - A single-audience role. Benefits - Base salary: $140,000 - $170,000 - Equity: The systems you'll work on touch every customer and Pro. - Healthcare: Medical, dental, and vision. - Fully remote: Work from anywhere in the US. - Flexible PTO: We Focus On Results.