[Hiring] Chief Operating Officer @LawnStarter

Role Description

We're hiring a COO to be the operational heartbeat of LawnStarter. 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.
• Marketplace operations are uniquely complex, requiring constant balancing of multiple service lines and seasonal demand.

What You'll Own:

• Driving a High-Performance Culture:
  • Operating cadence: Annual, quarterly, and weekly planning, done on time, with full preparation.
  • Initiative accountability: Swim lane leaders own their targets; you own the rigor.
  • Performance management: Activate rigorous tracking against existing scorecards for ~30 swim lane participants.
  • People development: Build the system we don't have: career pathing, growth plans, leadership development, succession planning.
• Driving Greenfield Initiatives:
  • Take new business lines from concept through the hard strategic decisions to scaled operation.

Problems to Solve:

• No operating cadence; annual and quarterly planning falls on the CEO.
• Initiatives slip and fall through the cracks; clear plans with timelines and milestones are lacking.
• We don't develop our people; no career pathing, growth plans, or succession planning.
• Greenfield ventures need a driver who can navigate total ambiguity and make hard strategic calls.

What Success Looks Like (Year 1):

• You've developed a high-performance culture throughout the organization.
• You're owning and scaling a greenfield initiative that comes out of our executive planning sessions.

Qualifications

• AI-native: Use AI tools daily to move faster.
• Relentlessly excellent: Set extremely high standards for yourself and everyone around you.
• A problem solver, not a playbook runner: Diagnose what's actually broken and build the right solution.
• A driver who creates momentum: Identify barriers and break through them.
• A change leader, not a change manager: Drive change with conviction and inspiration.
• Pragmatic to the core: Find the simplest, most effective solution.
• Battle-tested at this scale: Experience taking organizations from ~$30-50M in revenue to multiples of that.

Requirements

• Not a caretaker role; you're building what doesn't exist yet.
• Not a siloed operations job; you'll drive accountability across swim lanes and functions.
• Not easy; this is a complicated, two-sided marketplace business.
• Not a "strategy only" seat; you will set strategy and build the operating cadence.

Benefits

• Cash compensation: $300,000–$400,000
• Equity: TBD; this role directly drives company value.
• Healthcare: Medical, dental, and vision.
• Remote-first: Fully remote; ability to operate across time zones.
• PTO: Flexible time off, but there's a lot to do.