Chief Operating Officer (COO)

About LawnStarter

LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with $50M+ in net revenue across three brands. We've been profitable for three consecutive years, and our existing business has reached a place of great operating leverage: 38.5 cents of every incremental dollar in net revenue since 2022 has gone directly to the bottom line. We're entering our most ambitious phase yet, expanding into new verticals, building software products, and laying the foundation to become a multi-billion-dollar company. We have a really talented team of ~180 full-time members plus a seasonal workforce that scales to 500+.

The Role

We're hiring a COO to be the operational heartbeat of LawnStarter.

Here's what's true: we grew 20%+ last year, expanded EBITDA margin by 7 points, and scaled to $50M+ in net revenue. We have a great culture, a strong leadership team, a really talented team, and we're great at hiring. We've done a good job building a profitable, growing business, but we aren't strong operators yet.

We don't have the operational infrastructure, rigor, and discipline to match our ambitions. Structural people development is aspirational, not actual. And as the business gets more complex (multiple service lines, new verticals, software products) the CEO needs to elevate to focus on AI strategy, vision, and the highest-leverage bets.

This role is about taking a strong foundation and building the operating system on top of it. You'll be the person who ensures the entire organization continuously drives toward the vision, whether the CEO is in the room or not.

What makes this role different:

• You're not inheriting a well-oiled machine. You're building the operating system (cadence, accountability, performance management) largely from scratch.
• You'll take greenfield initiatives from executive strategy sessions and turn them into reality. You drive the hard execution decisions: one market or multiple? 1099 or W2? What's the org structure? Go or no-go? You bring it to fruition.
• Marketplace operations are uniquely complex. Two-sided dynamics, seasonal demand that swings your workforce from 180 to 500+, multiple service lines with different economics, and a Pro network that requires constant balancing. If you haven't operated in this kind of complexity, this isn't the right fit.

What You'll Own

Ultimately, you own two things:

1. Driving a High-Performance Culture

We define this as the combination of four things that reinforce each other:

• Operating cadence: Annual, quarterly, and weekly planning, done on time, with full preparation, complete metric sets, 13-week race plans, and systematic follow-through.
• Initiative accountability: Swim lane leaders own their targets. You own the rigor. Every major initiative has a plan, milestones, owner, and timeline — and you're the one who holds leaders to those commitments, calls out slippage early, and escalates when things stall. 4 of 5 swim lanes hit their annual targets.
• Performance management: Activate rigorous tracking against existing scorecards for ~30 swim lane participants. Performance issues addressed within 2 weeks.
• People development: Build the system we don't have: career pathing, growth plans, leadership development, succession planning. Zero regrettable A-player departures.

These aren't four separate jobs. They're one cultural transformation. The cadence creates visibility. Visibility enables accountability. Accountability surfaces who needs development. Development retains your best people. When this flywheel is spinning, you have a high-performance culture.

2. Driving Greenfield Initiatives

Take new business lines from concept through the hard strategic decisions to scaled operation. Should we launch W2? One market or many? One service or many? What's the org structure? Go or no-go? You navigate the ambiguity, make the calls, hire the team, and drive to an answer.

Direct reports: Shared Services, VP of Sales & Support, HR, Recruiting, GM of New Verticals (to be hired), plus new ventures (W2/Robomower) as launched.

Problems to Solve

There is no operating cadence. Annual and quarterly planning falls on the CEO and runs late. 13-week race plans don't exist for every swim lane. Accountability reviews happen at every level but are far from consistent. You need to own this entirely: the preparation, the metrics, the follow-through, so it runs without the CEO driving it.

Initiatives slip and fall through the cracks. People work hard, but there aren't clear plans with timelines and milestones. Things stall without anyone noticing. You need to install the discipline so that every initiative has a plan and every commitment gets tracked.

We don't develop our people. We say "people are critical" and we hire like it and build a culture like it. But we aren't structurally developing anyone. No career pathing, no growth plans, no succession planning. You need to build this from nothing.

Greenfield ventures need a driver. We have big ambitions (W2, Robomower, new verticals) but these require someone who can navigate total ambiguity, make hard strategic calls, hire the right people, and drive to a go/no-go decision. The CEO can't do this and grow the business.

What Success Looks Like (Year 1)

• You've developed a high-performance culture throughout the organization: operating cadence running on time, initiative accountability driving results across swim lanes, performance management rigorous and consistent, and people development structural and active.
• You're owning and scaling a greenfield initiative that comes out of our executive planning sessions and discovery.

Who You Are

AI-native. You use AI tools daily to move faster, whether that's analyzing data, drafting plans, running scenarios, or automating workflows. You don't just use what's handed to you; you experiment and push the boundary of what's possible. This is unlikely to be a good fit if you view AI as a nice-to-have rather than a fundamental way of working.

Relentlessly excellent. You set extremely high standards for yourself and everyone around you. "Good enough" makes you uncomfortable. You push for work you're genuinely proud of and you expect the same from your team. This is unlikely to be a good fit if you have a history of accepting mediocrity or avoiding hard conversations about quality.

A problem solver, not a playbook runner. You don't show up with a framework from your last company and force-fit it. You diagnose what's actually broken, figure out the right solution for this business, and build it. Marketplace operations are uniquely complex. You need to think from first principles, not templates. This is unlikely to be a good fit if your approach is "here's what I did at my last company" without adapting to context.

A driver who creates momentum. You don't wait to be told what to do. You see what needs to happen, you go find the barriers, and you break through them. When things stall, you're the one who unsticks them. This is unlikely to be a good fit if you need clear direction before you act or prefer to delegate problems rather than solve them.

A change leader, not a change manager. You're going to install systems and rigor where none exist. Our culture is adaptable, but regardless, people will resist. Old habits will reassert themselves. You need to drive change with enough conviction that it sticks and enough inspiration that people come with you, not just comply. This is unlikely to be a good fit if you avoid conflict or need consensus before making hard calls.

Pragmatic to the core. You find the simplest, most effective solution, not the most elegant or comprehensive one. You'd rather ship something good this week than something perfect next quarter. This is unlikely to be a good fit if you over-engineer solutions, get lost in analysis, or need every variable accounted for before you move.

Battle-tested at this scale. You've taken organizations from ~$30-50M in revenue to multiples of that, and you've done it more than once. You know what breaks at this stage and how to fix it. This is unlikely to be a good fit if your experience is primarily at large, well-structured companies where the operating infrastructure already existed.

This Role Is NOT

• A caretaker role. You're not maintaining what exists. You're building what doesn't exist yet. If you want a company with mature processes that just need optimization, this isn't it.

• A siloed operations job. You'll drive accountability across swim lanes and functions where most leaders don't report to you. This requires influence, not just authority.

• Easy. This is a complicated, two-sided marketplace business with seasonal dynamics, multiple service lines, and a workforce that scales 3x during peak season. The problems are hard and the ambitions are high. The upside is huge, but so is the work.

• A "strategy only" seat. You will set strategy for your areas, but the operating cadence, performance management, and accountability systems need to be built by you, not delegated to a chief of staff.

• Cash compensation: $300,000–$400,000

• Equity: TBD. This role directly drives company value and we want you invested in the outcome.

• Healthcare: Medical, dental, and vision

• Remote-first: Fully remote. This role requires the ability to operate across time zones and lead a distributed team.

• PTO: Flexible time off, but let's be honest, you're not joining for the PTO. There's a lot to do.