Director of Product Management

Job Overview

The Director of Product Management will define the operating model for LawnStarter’s product organization while leading a team of three Product Managers and supporting future hiring. You will own difficult tradeoffs across growth, retention, and profitability on a shared product roadmap.

You will also lead LawnStarter’s multi-service strategy, helping the business move from one profitable service category to a repeatable platform that can support additional home services. The role requires a player-coach who can develop strong Product Managers while remaining directly involved in the company’s most complex product decisions.

Key Responsibilities

• Lead, coach, and develop a team of three Product Managers.
• Hire additional product talent as the organization grows.
• Define product management standards, operating practices, and expectations for the team.
• Own prioritization across growth, customer retention, service quality, and profitability.
• Decide which initiatives move forward, which should wait, and which should be discontinued.
• Create a repeatable product strategy for expanding from lawn care into additional home service categories.
• Design product experiences that serve both homeowners and service professionals as one connected marketplace.
• Own LawnStarter’s product direction for artificial intelligence and agent-based experiences.
• Determine how AI agents should support internal teams, customers, service professionals, and future platform interactions.
• Partner closely with Engineering, Design, Data, Finance, Operations, Growth, and executive leadership.
• Maintain direct involvement in complex product discovery, strategy, scoping, and execution.
• Improve the quality and usability of LawnStarter’s core service experience.
• Help establish a scalable product foundation that supports multiple service categories without unnecessary platform fragmentation.

Strategic Product Challenges

• Transform a successful single-service marketplace into a flexible multi-service platform.
• Determine which product systems should be shared across services and which should remain service-specific.
• Develop approaches for evaluating service professional quality across different service categories.
• Create pricing systems that account for location, complexity, service type, and marketplace conditions.
• Improve quality assurance across lawn care, pool cleaning, and future home services.
• Balance roadmap demand across growth, retention, and profitability with limited engineering capacity.
• Develop product experiences for an environment where customers, workers, or buyers may increasingly interact through AI agents.
• Build an agent-native product roadmap without relying on an established industry playbook.

First-Year Success Measures

• Help the Product Management team deliver stronger outcomes, better scoping, and faster execution.
• Produce measurable improvements across growth, retention, and profitability.
• Advance the pool cleaning business toward profitable scale.
• Establish a repeatable product playbook for launching future service categories.
• Improve the quality of LawnStarter’s core lawn care experience.
• Develop a coordinated plan with the Growth team for reaching customers through AI-driven discovery channels.
• Create a clear agent-native product vision and begin implementing its first strategic initiatives.

Resume

• Experienced product leader who can combine team management with hands-on product work.
• Strong interest in artificial intelligence, agents, and emerging product interaction models.
• Regular user of AI who views agents as a major platform shift rather than only a productivity feature.
• Ability to develop strong Product Managers through coaching, feedback, and thoughtful delegation.
• Systems thinker who understands marketplace inputs, incentives, feedback loops, and second-order effects.
• Strong prioritization skills with the confidence to decline lower-value work.
• Ability to build trust across Engineering, Design, Data, Finance, Operations, and Growth teams.
• Deep attention to product scope, usability, and customer experience.
• Comfort operating without a finished playbook or established process.
• Ability to work effectively in a distributed, remote-first company.

Leadership Approach

• Operate as a player-coach rather than a purely administrative manager.
• Stay involved in difficult product problems instead of only assigning work.
• Raise the standard of an already capable Product Management team.
• Lead without over-controlling team members.
• Support independent thinking while maintaining accountability for outcomes.
• Make clear roadmap decisions and explain the reasoning behind tradeoffs.

What This Role Is Not

• It is not a people-management-only position.
• It is not an individual contributor role without direct reports.
• It is not a turnaround assignment for a struggling team.
• It is not suitable for someone who is skeptical about AI and agent-driven products.
• It does not come with a completed playbook for multi-service marketplace expansion.

Work Arrangement

• Fully remote position within the United States.
• Full-time employment.
• Available to candidates across approved U.S. locations.
• Leads a distributed Product Management team.
• Works closely with the Vice President of Product and senior cross-functional leaders.

Compensation

The annual base salary range for this position is $200,000 to $250,000.

The compensation package also includes a significant leadership equity grant, allowing the successful candidate to participate directly in the company’s long-term growth and performance.

Benefits

• Significant leadership equity package.
• Medical insurance.
• Dental insurance.
• Vision insurance.
• Flexible paid time off.
• Fully remote work from anywhere within the United States.
• High-trust work environment focused on outcomes.

About LawnStarter

LawnStarter operates an on-demand marketplace connecting homeowners with lawn care and outdoor service professionals. The company manages more than $100 million in annual bookings across LawnStarter, Lawn Love, and Home Gnome through one shared platform.

After building a profitable lawn care marketplace, LawnStarter is expanding into additional home service categories. Pool cleaning is currently available in selected markets as the company develops a repeatable model for future service expansion.