Director of Product Management

What Makes This Role Different

You build the layer, not inherit it. This is a brand-new layer between the VP and the PMs. You define how the team works, the bar for the craft, and the operating model — you’re not slotting into someone else’s machine.
It’s a marketplace, so the obvious answer is usually wrong. Change a price and you move conversion, Pro claim rates, margin, and retention all at once. Almost every decision has second-order effects across customers, Pros, and the business. You think in systems, not features.
You multiply a strong team — this isn’t a turnaround. The PMs are already good. The job is to get extraordinary outcomes from extraordinary people while still doing the hardest work yourself. Player-coach, not figurehead.
Strategic bets and patient optimization, both. You’ll open new verticals and compound a few points of conversion at a time — and know which the moment calls for.

What You’ll Own

The PM team: Lead, coach, and multiply three already-strong PMs — and hire more as we grow.
Prioritization: Own the growth/retention/profitability tradeoffs on one shared roadmap — what gets built, what waits, what we kill.
Multi-service strategy: Turn one proven vertical into a repeatable playbook across services, designing for customers and Pros as one system.
Agent-native direction: Own how AI and agents show up in what we build — for our team, our customers, and our Pros.
Cross-functional partnership: Be the product leader the rest of the company trusts to make the right calls.

Requirements

Who You Are

AI-native and agent-curious. You use AI every day and push the team to do the same. You believe agents are the next platform shift, and you’re energized by the open question of what an agent-driven world means for LawnStarter — a genuine thought partner on it, not someone who shows up with all the answers. This is unlikely to be a good fit if you treat AI as a productivity hack.

A player-coach who multiplies talent. You get extraordinary outcomes from already-strong people — coaching, raising the bar, unblocking — and you still do the hardest work yourself when it counts. You know the difference between leading and controlling. This is unlikely to be a good fit if you need to “fix” a broken team to feel useful, or if you’ve moved fully into management and don’t want to touch the product directly.

A systems thinker. You see inputs, rules, feedback loops, and second-order effects, and you hold the customer side and the Pro side in your head as one connected machine. This is unlikely to be a good fit if you think in isolated features and miss how a change ripples through the rest of the system.

A brutal prioritizer. You say no well — you sequence ruthlessly, kill good-but-not-now work, and protect the team’s focus. This is unlikely to be a good fit if you avoid the hard conversations prioritization requires.

A great cross-functional partner. You earn the trust of designers, engineers, data, finance, and ops by speaking their language and making decisions they respect. This is unlikely to be a good fit if you treat other functions as service providers rather than partners.

Obsessive about scoping and user experience. You cut scope to the essential and sweat how the product actually feels to use. This is unlikely to be a good fit if you ship the first version that technically works without caring whether it’s genuinely good.