Marketplace Dynamics & AI-First Pricing Strategist

About LawnStarter

LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, spanning three brands: LawnStarter, Lawn Love, and Home Gnome. They’ve cleared $750M in bookings and turned a profit for three consecutive years. Founded in Austin in 2013, the company scales from 180 employees to over 500 during peak season. The marketplace operates by matching customer requests with eligible Pros, managing recurring services, and ensuring seamless consumer-provider relationships.

The company is entering its most ambitious phase, expanding into new verticals, developing software products, and laying the groundwork to become a multi-billion-dollar enterprise.

One of their core values is ‘AI or Extinction’: every task must be approached with an AI-first mindset. This role is designed for top-tier performers who meet this bar.

The Role

This position focuses on optimizing marketplace dynamics, balancing pricing, Pro incentives, and supply planning. The role requires developing a system from scratch to drive success across hundreds of markets simultaneously. You’ll start as an individual contributor with no direct reports, reporting directly to the COO. Hiring will follow after proving the model’s effectiveness. The role is new, meaning much of the work remains unframed.

The share of services completed by top Pros is below desired levels, impacting retention and customer experience. No single team currently owns the balance between customer and Pro sides of the marketplace or drives market-by-market improvements. This role changes that.

What Makes This Role Different:

• You’ll lead cross-functional efforts to adjust pricing, incentives, and supply planning, collaborating closely with Product, Growth, Finance, and Operations.
• You’ll be an advanced user and builder of Brain, LawnStarter’s internal AI toolkit powered by Claude Code. This tool supports metric queries, document drafting, bug triage, and more. Expect to leverage AI to build systems and processes that accelerate business outcomes.
• You’ll own outcomes end-to-end, from strategy to execution. Strategy without follow-through won’t suffice.

What You’ll Own

• Pricing: Manage instant quotes, manual quotes, dynamic pricing, and pre-spring seasonal tests. Pricing balances the marketplace in real time, determining which jobs customers book and which Pros claim. Collaborate with product teams to refine automated pricing tools and strategies.
• Pro Incentives and Supply Planning: Design and test incentive programs with Pros in the field, not just in spreadsheets. Build agentic tools to automate market-by-market and service-by-service planning, ensuring responsible supply ahead of seasonal demand.
• Matching and Service Completion Rate: Partner with a Senior Product Manager to improve job distribution and matching. The Service Completion Rate (share of new customers completing their first service within seven days) is a key metric for this role.

Problems to Solve

Raise the Service Completion Rate costing customers.

Many new customers fail to complete their first service within the first week. Causes span pricing, matching, customer expectations, and Pro supply. Fixing this requires addressing the entire chain, not just one link. Identify where jobs fall through, determine the binding constraint (price, incentive, planning, or matching), and implement solutions alongside Product. Many fixes will involve long-term strategies to improve Pro quality in specific markets.

Get ahead of a wildly seasonal marketplace.

Demand for lawn care spikes in spring and drops by December. Supply must align with this curve, market by market and service by service. Build forecasting and monitoring tools, and establish an operating rhythm to stay ahead of demand rather than reacting to it. Spring is critical.

Make pricing a real-time balancing lever.

Price adjustments move both sides of the marketplace faster than any other factor. Dynamic pricing, instant quotes, and manual quotes must work cohesively. Initial tests proving a change’s effectiveness must be designed, instrumented, and operational before spring demand peaks. You’ll own the model, experiment design, and decision rights on whether changes improve completion and margin or trade one for the other.

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

Pros are independent operators who decide which jobs to claim. Craft programs using incentives, surge pricing, take rate, and more to lift completion rates and improve economics. Continuously test ideas and improve results with Pros in the field.

What Success Looks Like (Year 1)

• The Service Completion Rate improves meaningfully, with clear traceability to pricing, incentive, and matching decisions.
• Automated pricing and dynamic market-balancing tools are live and demonstrably increase contribution LTV.
• You’ve built a system of tools and agentic systems that transition LawnStarter from managing supply and demand with a sledgehammer to a scalpel.
• The COO can present you with any supply or demand problem and trust you’ll provide data, recommendations, and an execution plan.

Requirements

Who You Are

An elite AI builder. You think in terms of agentic systems, building agents, evals, and context engineering. You stay ahead of AI frontiers and apply new capabilities quickly—within days, not quarters. You’re in the top few percent of AI users at any company you’ve worked for. Those who treat AI as an occasional assistant or need engineers to build tooling for them won’t fit here.

Marketplace-balanced. You have hands-on experience with the complex dynamics of a two-sided marketplace. You understand what happens when one side outpaces the other. This role is unlikely to suit those with experience only in simple single-sided businesses.

A pricing owner. You’ve owned dynamic pricing, quoting, or yield decisions where errors directly impacted the P&L. You make informed recommendations, test them, and own the results.

A modeler, not a requester. You build forecasting and incentive-elasticity models yourself using the tools that get you there fastest. If your first instinct is to file a request with analytics and wait for results, this role isn’t for you.

A partner who drives strategy collaboratively. You work well with people outside your direct reports. For example, the Service Completion Rate depends on cross-functional alignment between pricing, incentives, planning, and matching. If you need formal authority to effect change, this role isn’t for you.

A finisher. Execution matters as much as strategy. If you treat strategy as your job and execution as someone else’s, this role isn’t for you.

Degree in analytics, business, or a 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 initially.
• A fit for anyone who isn’t already an elite AI builder. The AI bar here is not aspirational; it’s the baseline for hiring.
• A role with a slow quarter to ease into. Spring demand is make-or-break, and it arrives regardless of readiness.
• A strategy-only seat. You’ll execute recommendations rather than handing them off to someone else.