Director of Operations, Service Delivery

The Role

This is a biz ops generalist role, built for someone who wants to work across many parts of the business instead of owning one narrow lane. You'll start as an individual contributor with no direct reports, in a new seat reporting directly to the COO. Your first owned area will be building Service Delivery into a working operational function. This will entail adding structure, visibility and process to the way we ensure as many customer jobs as possible are completed successfully and on time by LawnStarter Pros, in lawn care and other services we offer now and over time.

New projects will show up unscoped over time. That's by design. As LawnStarter enters new verticals and grows toward a multi-billion-dollar future, big problems will keep surfacing with no obvious owner, and you'll be one of the people the COO trusts to run them down.

What makes this role different:

• You work on some of the biggest company-wide projects, cutting across teams and functional areas.
• You'll be a top 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. Every project you run is built AI-first: the analysis, the tooling, the process automation, the monitoring. You build it yourself instead of waiting on an analyst or engineer.
• You own outcomes end to end, from recommendation through execution. Strategy without follow-through doesn't count here.

What You'll Own

• Service Delivery, from the ground up. Despite LawnStarter's considerable scale and reach, Service Delivery doesn't exist yet as a dedicated function. You'll help define the standards we should meet for job completion rates and speed, measure whether we hit them, and design processes, incentives and real-time interventions that get tested with Pros and customers in the field to lift performance. Scope covers every vertical and every delivery model, from today's 1099 Pros to potential W-2 crews under future evaluation.
• Raising customer & Pro retention rates. When we deliver service with excellence, Pros and customers alike stay with us longer. Working tightly with peers across Product, Data and Support, you'll identify new opportunities for us to boost retention and LTV and play a key role in driving resulting initiatives cross-functionally.
• Whatever comes next. New projects will land on your plate as the company grows into new verticals and builds new software products. You'll take them from "we should look into this" to building and then running systems with structure, KPIs and owners.

Problems to Solve

Build a Service Delivery function that doesn't exist yet. Right now, no one formally owns whether LawnStarter delivers the service it promises. You'll define the standard for what a Pro should deliver, then build the agents and pipelines that measure adherence to it and run the tests that change behaviors and outcomes in the field.

Move metrics. Leverage systems thinking and AI expertise to drive business results that sit across various functional teams. That means untangling handoffs where several teams touch a problem or goal and no one team owns the outcome.

Take unscoped problems from ideas to fully-running and automated systems. Some of the most important work here hasn't been named yet. At some point, someone will raise a fuzzy, unframed problem and say it needs attention. Your job is to take that starting point and build whatever tooling or process it needs, at record speed, and hand back something that runs, with a clear owner and quantitative targets attached.

What Success Looks Like (Year 1)

• Service Delivery is a working function with a defined (and elevated) service standard, a way to measure adherence to it, clear SOPs, and an intervention and incentive playbook that's been tested and proven to lift results.
• At least one project nobody had scoped a year earlier has gone from "we should look into this" to a heavily-automated, running system with a named owner and tracked KPIs.
• Tools you built with AI are in daily use by people other than you, and the way you work has raised the bar for how the company uses AI.
• The COO can hand you a gray-area 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.

A zero-to-one operator. You've taken ambiguous, cross-team operating problems from zero to running systems as an individual contributor, with no team to hand the work to. This is unlikely to be a good fit if your experience stops at executing a scope someone else already defined.

Marketplace-tested. You've operated inside a marketplace or another multi-sided business and felt firsthand what it takes to balance the needs of different stakeholders on the supply and demand sides. A background built entirely on single-sided businesses, with one stakeholder type to satisfy, won't translate here.

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.

A partner who can help drive strategy collaboratively. You work well with people who don't report to you and are a savvy cross-departmental collaborator on priorities and sequencing. If you need formal authority to effect change, this role isn't for you.

Data-driven by reflex. You'd rather build the query or the dashboard than argue from a hunch. This is unlikely to be a good fit if, when ambiguity hits, your first move is to guess and move on instead of digging for the number.

At home in unresolved ambiguity. Scope shifts as priorities do, and problems arrive unframed more often than not. That's the norm here, not an exception.

Degree in analytics, business or related field, with 7+ years of experience in marketplace 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 strategy-only seat. You'll execute what you recommend, not hand it off to someone else to run.
• 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.

Benefits

Compensation & Benefits

• Base salary: $175,000 to $200,000.
• Equity component: We want the person who takes this role invested in LawnStarter delivering excellent service, 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.