What We’re Building

The U.S. real estate brokerage market generates more than $100 billion a year in commissions, funneled through a brokerage model that hasn’t fundamentally changed in half a century. Roughly one in three transactions today is driven by an investor, and investors are the segment most actively looking for something better — because they’re the ones who feel the friction every week instead of once a decade. PropertyPilot is being built for them first: the property data, analysis, and deal flow platform the brokerage model never delivered, spanning 175 million properties across every asset class. The investor wedge is a real business on its own. But it’s also the proof point for something much larger — if we serve professional buyers better than the incumbents, the path opens to serving every buyer that way. We’re hiring our first Head of Growth to own that journey from the start.

Position Summary

PropertyPilot is looking for a Head of Growth to build and execute the go-to-market motion from the ground up. You’ll run disciplined growth experiments across paid, organic, content, partnerships, and community — measuring CAC, payback, and activation with rigor, killing what doesn’t work, and pouring fuel on what does. The playbook you build — sourcing investors, instrumenting the funnel, and codifying what scales — becomes the foundation for every market we enter next.

This is a player-coach role. You’ll run the experiments yourself in the early days, then hire and lead a small team as the model proves out. You report directly to the CEO and partner daily with Product and Engineering. The growth motion you prove becomes the foundation of our funding narrative and the engine that takes us from investor wedge to category leader.

What You’ll Own

You’re the first growth hire and the operating owner of GTM. Day one, you own the number. Year one, you’ve built the playbook the whole company runs on.

The growth engine. Every channel that gets investors into the product — paid, organic, content, community, partnerships, outbound, referral. You decide the mix, you run the tests, you find what works.
The numbers that matter. CAC, payback, LTV, activation, retention, viral coefficient. You set the targets, you build the dashboards, you defend the math.
Creative customer acquisition. Direct mail that actually gets opened. Outbound that doesn’t read like outbound. Referral mechanics that compound. Content that ranks. You’re as comfortable writing the copy as reading the cohort data.
Pricing, packaging, and monetization. Partner with the CEO and Product on the decisions that compound — free-to-paid conversion, paywall design, plan structure, what the credit economy rewards.
In-product growth. Co-design the activation funnel, the paywalls, the referral surfaces, the onboarding. Growth and product are the same conversation at PropertyPilot.
The next round. Your playbook is the Series A narrative. Capital-efficient, repeatable, defensible — the model that turns a beachhead into a category.
The team. The first hire is you - Build a small, sharp growth team as the motion proves out.

What You Bring

You’ve run growth at a 0>1 or early-stage company and you’ve seen what works when no one hands you a playbook.
You’ve built acquisition motions that scaled — and you have the CAC, payback, and retention numbers to prove it.
You’re fluent across paid, organic, content, lifecycle, and at least one community or outbound channel. Mono-channel specialists won’t enjoy this role.
You think in experiments, not campaigns. You ship, measure, adjust, repeat.
You’re a creative acquisition operator first and a marketer second. You’d rather write the ad than approve it.
You use AI tools daily — Claude, ChatGPT, Clay, whatever earns its keep — because they make you faster. You’re curious about building agents that compound your output, not afraid of them.
You can read a funnel without a dedicated analyst. Mixpanel, Amplitude, whatever — you can instrument it and act on it.
You’re a clear writer. The role demands it.
Real estate, proptech, fintech, marketplace, or vertical SaaS experience helps. So does selling to operators. Neither is required.

Who You Are

Hungry. You want the upside that comes with being early at a company building something that hasn’t been built before. A safer role at a bigger company isn’t what you’re looking for.
A builder. You’re energized by a direct CEO report, daily partnership with product and engineering, and full ownership of a number. No middle layers, no politics, no buffer.
A player-coach. You’ll be sourcing prospects, writing copy, and shipping experiments yourself in the early innings — and you want it that way. Leadership comes from doing the work, not delegating it.
Scrappy. You’ve built funnels on small budgets and know how to win with community, content, and clever outbound before paid.
Sharp. You don’t ship what you can’t measure. You don’t promise what you can’t defend. And you don’t waste anyone’s time — including your own.
You Value Face Time. Being on-site 4 days a week at our office in Manasquan, NJ or NYC is a plus, not a trade-off, for you.

PropertyPilot is an Equal Opportunity Employer.

AI disclosure: As part of our recruiting process, PropertyPilot may use AI-assisted tools to help screen, review, and organize applications, as well as to support scheduling and communication. These tools assist our team and all final hiring decisions are made by humans. We work to ensure these tools are used fairly and without unlawful bias. If you have questions about how AI is used in your application, would like to request a reasonable accommodation or an alternative review process, please contact us at (848) 321-5588.

PropertyPilot

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Head of Growth (GTM)