Chief Operating Officer (COO)

LawnStarter

5h•$300,000 - $400,000•Remote

About The Position

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+. 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.

Requirements

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.