Head of Product, ProBase

About LawnStarter

LawnStarter is the nation's leading on-demand marketplace for lawn care and related services, with over $100M in annual bookings. We're expanding beyond lawn care to become the one-stop shop for all home services—and ProBase is our first major bet in that direction.

About ProBase

ProBase is a free software platform for home service professionals, starting with pool maintenance operators. Our thesis is simple: give pros the tools to run their business for free, help them get more customers, and some will choose to get jobs through our marketplace. We're not a SaaS company charging $50/month—we're building a new on-ramp to the LawnStarter ecosystem.

The Role

This is not a typical product management role. We're looking for someone to take ProBase and run with it—like a founder, but with the backing of LawnStarter's resources, brand, and marketplace.

You'll be an individual contributor with GM-level accountability. Small team, big ownership. You won't be managing a large org; you'll be shipping product, talking to customers, and making the calls that determine whether ProBase succeeds.

What makes this role different:

• Entrepreneurial ownership: You're not executing someone else's roadmap. You're building the roadmap, validating it with customers, and iterating fast.
• IC + GM hybrid: You'll be hands-on (writing specs, reviewing designs, prioritizing bugs) while also owning business outcomes (user growth, activation, marketplace conversion).
• Rethinking the category: We're not building "Skimmer but free." We're asking what pro software should look like if you started from scratch today—with AI, modern mobile UX, and a marketplace behind it. You'll have the freedom to challenge assumptions and build something genuinely new.
• Direct customer contact: You'll spend real time with pool pros—understanding their workflows, watching them use the product, learning what "simple" actually means to someone working from their truck.
• Full-stack product work: Strategy, discovery, execution, go-to-market. You'll work across all of it because that's what early-stage products require.

What You'll Own

• Product strategy: Define where ProBase goes and why. Make bets on which features matter, which segments to prioritize, and how to differentiate from Skimmer, Pool Brain, and Jobber.
• User growth: Own the path from 0 to 10k+ MAUs. Figure out what drives signups, activation, and retention for pool pros who've never used software before.
• Marketplace integration: Build the bridge from "free software user" to "LawnStarter marketplace provider." This is how ProBase creates value for the business.
• Roadmap and execution: Prioritize ruthlessly. Work with engineering and design to ship fast and learn faster.
• Customer insight: Be the person who knows pool pros better than anyone else at LawnStarter. Their pain points, their workflows, their objections, their language.

Problems to Solve

Getting pool pros to try software for the first time: 70% of our target market uses pen and paper. They're not searching for "pool service software"—they don't know it exists or think they need it. How do we reach them? How do we convince them that free software is real and not a trap?

Making "simple" actually simple: Pool pros tell us existing software is "too complicated." But what does that mean? Is it too many features? Bad mobile UX? Confusing onboarding? You'll need to figure out what simple really means and build for it.

Proving the marketplace flywheel: Our bet is that free software → engaged users → marketplace conversion. But we need to prove this works. What's the right moment to introduce marketplace jobs? How do we make it feel like a benefit, not a bait-and-switch?

Competing with free (pen and paper): Our biggest competitor isn't Skimmer—it's the status quo. How do we make the case that even free software is worth the effort of switching from a routine that "works fine"?

Expanding beyond pool: Pool is our beachhead. But ProBase needs to work for lawn care, handyman, and other verticals eventually. How do we build a foundation that scales without over-engineering for hypothetical futures?

What Success Looks Like (Year 1)

• 10k+ Monthly Active Users (stretch goal)
• Marketplace integration live and working
• 1,000 ProBase users converted to LawnStarter marketplace
• Clear retention signal: users who try ProBase stick with it
• Validated positioning: we know why pool pros choose us over alternatives

Requirements

Who You Are

You've built products from scratch. You have real experience taking something from zero to one—not inheriting a product at scale and optimizing it. You know what it feels like when nothing exists yet and you have to figure out what to build first.

Founder experience is a big plus. If you've started something yourself (even if it failed), you understand the mindset we need. Resourcefulness, ownership, comfort with ambiguity.

You're obsessed with customers, not features. You'd rather spend an hour watching a pool pro use their phone than debating product frameworks. You get energy from talking to users, not from internal meetings.

You're a clear, direct communicator. You write well. You can explain complex ideas simply. You're comfortable saying "no" with reasons and "I don't know" when you don't.

You move fast and fix things. You have a bias for action. You'd rather ship something imperfect and learn than wait for certainty. You're not precious about your ideas.

You think in possibilities, not constraints. You're excited about AI and what it unlocks for product experiences. You don't want to copy incumbents—you want to ask "what should this be?" and build something better. You stay curious about emerging tools and approaches.

You can go deep on details. You're not above writing a bug report, QA-ing a release, or digging into analytics to understand a drop in activation. IC means IC.

This Role Is NOT

• A team-building role: You might hire 1-2 people eventually, but this isn't about building an empire. If you're excited about "growing a team," this isn't the right fit.
• A strategy-only role: You'll be in the weeds. Specs, designs, customer calls, launch checklists. If you want to set direction and have others execute, look elsewhere.
• A role with a clear playbook: We're figuring this out as we go. If you need defined processes and established ways of working, this will be frustrating.
• A cushy job: This is hard, ambiguous work. You'll face problems without obvious answers, make decisions with incomplete information, and learn by doing. If you want a role where someone else has figured it out and you just execute, this will be frustrating.

Benefits

• Equity: Significant equity package—we want you to benefit from ProBase's success

• Competitive base salary: 180k to 210k USD annually
• Healthcare: Medical, dental, and vision
• Fully remote: Work from anywhere in the US
• Unlimited PTO: We focus on results. Take the time you need to recharge or enjoy life, work hard when you are back.

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.