The Role

This role owns marketplace dynamics. Pricing sits on one side, Pro incentives and supply planning on the other. This is a complicated multivariate equation that needs a person who can understand the complicated optimization of scaling markets profitably while driving happier customers and pros. They need to be able to develop the system essentially from scratch that can drive success across hundreds of markets simultaneously. You'll start as an individual contributor with no direct reports, in a new seat reporting to the COO. Hiring comes after you've proven the model works. The seat is new, so plenty of the work arrives unframed. That's the working condition here, not an exception to it.

The share of services completed by top pros is short of where it needs to be, harming retention and our customer experience. Nobody owns balancing the two sides of this marketplace or driving market by market improvements as one job today; this role changes that.
What makes this role different:

• You'll move pricing, incentives, and supply planning by leading a broad cross-functional effort. You'll partner especially tightly with Product, Growth, Finance and Operations.
• You'll be a top user and builder in Brain, LawnStarter's internal AI toolkit built on Claude Code that already powers everything we do across the company: metric queries, document drafting, bug triage, and more. We expect you to approach your work in an AI-first fashion, leveraging Brain to build new systems and processes that will push the limits of how fast AI can accelerate business results.
• You'll own outcomes end to end, from recommendation through execution. Strategy without follow-through doesn't count here.

What You'll Own

• Pricing. Instant quotes, manual quotes, dynamic pricing, and the pricing tests that need to be running before our spring seasonal peak. Price is what balances the two sides of this marketplace in real time: it decides which jobs customers book and which jobs Pros are willing to claim. You will work with the product teams who build the tools around automated pricing and help facilitate ideas on how to make those more effective. The strategy for actually pricing is yours.
• Pro incentives and supply planning. Incentive design that gets tested with Pros in the field, not modeled in a spreadsheet. Build agentic tools to automate planning market by market and service by service. Build supply responsibly ahead of the seasonal ramp so we don't need to chase it later.
• Matching and Service Completion Rate, shared with Product. Service Completion Rate, the share of new customers whose first service completes within seven days of signup, is a number this role is judged on. You'll partner tightly with a Senior Product Manager who runs the job distribution and matching roadmap. You bring the pricing, incentive, and planning levers; they bring the matching and distribution product.

Problems to Solve

Raise the Service Completion Rate that is costing us customers.

Too many new customers don't get a first service completed in their first week after signing up. The causes run across pricing, matching, customer expectations, and Pro supply, so fixing it means working the whole chain rather than one link. You'll find where jobs fall out, decide whether price, incentive, planning, or matching is the binding constraint in that market, and then go fix it alongside Product. Lots of these fixes will come with long term strategies to move the pro quality needle in specific markets rather than instant optimization.

Get ahead of a wildly seasonal marketplace.

Demand for lawn care doesn't move gently through the year. It climbs toward May and then falls by December, and the climb is fast. Supply has to track that curve, market by market and service by service. You'll build the forecasting and monitoring yourself, plus the operating rhythm that gets LawnStarter out ahead of the ramp instead of reacting to it. Spring is make-or-break.

Make pricing a real-time balancing lever.

Price moves both sides of the marketplace faster than anything else. Dynamic pricing, instant quotes, and manual quotes all need to work as a cohesive system, and the initial tests that prove out a change have to be designed, instrumented, and running before spring demand arrives. You'll own the model, the experiment design, and decision rights on whether a change lifted completion and margin or traded one for the other.

Design a playbook of levers that change behavior and protect spend.

Pros are independent operators who decide for themselves which jobs to claim. You'll craft programs leveraging incentives, surge pricing, take rate and more to lift completion rates and improve economics. Test ideas and continuously improve results with Pros in the field.
What Success Looks Like (Year 1)

• Service Completion Rate has moved meaningfully in the right direction, and we can trace which pricing, incentive, and matching decisions moved it.
• Automated pricing and other dynamic market-balancing tools are live and demonstrably lifting contribution LTV.
• You've built the system of tools and agentic system that take us from managing supply and demand with a sledgehammer to a scalpel.
• The COO can hand you a supply or demand problem with no playbook and trust that what comes back is data, a recommendation, and a plan to execute it.

Requirements
Who You Are

An elite AI builder. You think in terms of agentic systems. Building agents, evals, context engineering, and thinking in guardrails are core to who you are. You keep up with the frontier and put new capabilities to work within days, not quarters. You'd be in the top few percent of AI users at any company you've worked at. Someone who treats AI as an occasional assistant, or needs an engineer to build tooling for them, isn't the right fit here.

Marketplace-balanced. You have meaningful experience with the complicated dynamics inside a two-sided marketplace. You've felt what happens when one side outruns the other. This is unlikely to be a good fit if your experience is built entirely on simple single-sided businesses.

A pricing owner. You've owned dynamic pricing, quoting, or yield decisions where being wrong showed up in the P&L rather than in a retro. You make informed recommendations, test them and own the results.

A modeler, not a requester. You build the forecasting and incentive-elasticity models yourself, in whatever tooling gets you there fastest. This is unlikely to be a good fit if your first instinct is to file a request with analytics and wait for a read.

A partner who can help drive strategy collaboratively. You work well with people who don't report to you. Service Completion Rate is the clearest case: you don't control the matching roadmap and Product doesn't control price or incentives, so the result depends on cross-functional alignment on priorities and sequencing. If you need formal authority to effect change, this role isn't for you.

A finisher. Executing what you recommend matters as much to you as the recommendation itself. This is unlikely to be a good fit if you treat strategy as your job and execution as someone else's.

Degree in analytics, business or related field, or 7+ years of experience in marketplace supply and demand, operations or equivalent roles.

This Role Is NOT

• A people-management role. There's no team to build or manage, at least not to start.
• A fit for anyone who isn't already an elite AI builder. The AI bar on this team isn't aspirational; it's the baseline we hire against.
• A role with a slow quarter to ease into. Spring decides the year, and it arrives whether or not you're ready for it.
• A strategy-only seat. You'll execute what you recommend, not hand it off to someone else to run.

Benefits
Compensation & Benefits

• Base salary: $185,000 to $230,000.
• Equity component: We want the person who takes this role invested in whether the marketplace delivers the service it promises, and in how far AI-first operating carries this company.
• Healthcare: Medical, dental, and vision.
• Fully remote (US): All of LawnStarter is remote. This role demands deep independent work and close partnership across a distributed, multi-country team.
• Flexible time off: We focus on results. Take what you need.