Vice President Engineering Jobs in Santa Rosa, CA

About LawnStarter

LawnStarter is the nation's leading on-demand marketplace for lawn care and outdoor services, with over $100M in annual bookings. We operate across three brands (LawnStarter, Lawn Love, Home Gnome) on a single shared platform, and we've been profitable for two years running. We're expanding beyond lawn care to become the one-stop shop for all home services.

About Product at LawnStarter

Home services is a massive, broken market. For homeowners, getting reliable, fairly priced service is a hassle of phone tag, no-shows, and surprise quotes. For the Pros who do the work, running a business means chasing customers, dead time between jobs, and unpaid admin. LawnStarter is the marketplace that fixes both sides.

We proved the model with lawn care - it works at scale, profitably, across millions of jobs. In the last year we extended it to a second service: pool cleaning, now live in select markets. Getting there meant building the first version of a product that can onboard customers and Pros, match the two sides, get the job done, and handle the exceptions when it doesn't go to plan.

The Role

This is LawnStarter's first Director of Product Management - the leader between the VP of Product and a team of three PMs (and the hires that follow).

The mandate is simple to state and hard to do: ship value across growth, retention, and profitability by building a great product for customers and Pros. Concretely, that means taking us from one profitable-at-scale vertical to two, setting the path from two to n, while still aggressively improving our core lawn service.

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.

Problems to Solve

Abstracting one product into a multi-service platform. Every service has different economics, quality signals, and Pro workflows. How do we judge Pro quality when services are nothing alike? Price any service by location and job complexity? Guarantee quality on every job, not just lawns? You'll decide what generalizes and what stays service-specific, then sequence the build to a second profitable vertical - a platform that absorbs that variation instead of forking under it.

Prioritizing across three goals with one capacity. Growth, retention, and profitability all want the roadmap, and engineering capacity is finite - a win on one can cost you on another. You'll own the sequencing and tradeoffs, and say no clearly and often, with reasons people respect.

Building for the agent era. We believe products must now be built to use agents (to move faster and serve customers and Pros better) and to serve agents (so the platform works when the buyer or the worker is an AI). Almost no one has a playbook for this - you'll help write ours.

What Success Looks Like (Year 1)

• The team ships at a higher ceiling: The same strong PMs are visibly doing their best work - better outcomes, sharper scoping, faster shipping.
• Wins in all three goals: Measurable progress on growth, retention, and profitability - not one at the expense of the others.
• Second vertical on track: Pool cleaning progressing toward profitable-at-scale, with a repeatable playbook for the verticals after it taking shape.
• A stronger brand through quality: Measurable improvement in the quality of our core service, and a clear plan with the growth team to win AI-driven channels.
• An agent-native vision: A clear roadmap for winning in an agent-driven world, with the first bets already underway.

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.

This Role Is NOT

• A pure people-management role. You lead a team and stay in the work - the hardest problems are yours to help solve, not just to assign. If you don't want to touch a spec again, this isn't it.
• A solo-IC role. You lead and grow a team. If you want to own a domain alone with no reports, look at our Senior PM roles instead.
• A turnaround. The team is already strong. If you're energized by fixing broken teams, this won't scratch that itch.
• A fit for an AI skeptic. We believe the agent shift is real and urgent. If you're not convinced, you'll be fighting the company's direction.
• A role with a finished playbook. Multi-service and agent-native product are things we're figuring out as we go. If you need established processes and proven paths, this will be frustrating.

Benefits

• Equity: A significant leadership equity package. You'll have high impact on our growth, retention, and profitability. We want you invested in that outcome.

• Base salary: 200k - 250k
• Healthcare: Medical, dental, and vision.
• Fully remote: Work from anywhere in the US. Leading a distributed team and doing deep product work both require focus and trust - we give you both.
• Flexible PTO: We focus on results. Take what you need.

LawnStarter provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. We comply with applicable state and local laws governing nondiscrimination in employment.