The mission

The marine industry runs on clipboards, phone calls, and software from the 90s. Marinas manage millions in revenue through spreadsheets. Boaters call ahead and hope for the best. An entire economy—one that touches coastal communities, family businesses, and a way of life—operates without the infrastructure it deserves.

Dockwa is changing that. We're building the operating system for everything that floats.

We've spent a decade earning the trust of marinas and boaters across North America. We're now the system of record for thousands of marinas and the booking platform for hundreds of thousands of boaters. Every transaction, reservation, fuel purchase, and contract flows through our platform—creating the data layer that will power the next generation of marine commerce.

We need a VP of Engineering to build the team and technology that turns this foundation into something transformational.

About the role

This is an inflection point. We've proven product-market fit. We've built the network. We've established category leadership. Now we need to evolve from a marina management tool into the intelligence layer for an entire industry.

That means shipping new products faster. Scaling our payments infrastructure globally. Building AI-powered capabilities that help marinas optimize yield, manage operations, and make better decisions. Creating platform APIs that third parties build on top of.

The technical challenges are real: multi-sided marketplaces, embedded payments, dynamic pricing, international expansion, and data products that monetize a decade of transaction history. You'll need to solve these while scaling a lean engineering organization that has always punched above its weight.

This isn't a role for someone who wants to optimize an existing machine. It's for someone who wants to build the machine that captures a massive market before anyone else figures out it exists.

Core responsibilities

Build an Engineering Organization That Ships

You'll inherit a small, talented R&D team and a proven Engineering Lead who knows the codebase and the domain. Your job is to scale this team thoughtfully—adding senior ICs and leads who can own problems end-to-end, building a pod structure that aligns with our product bets, and creating a remote-first culture where great engineers want to stay and grow.

We don't need process for process's sake. We need an organization that maintains velocity and quality as it grows.

Drive Technical Strategy Across Three Product Vectors

Our growth comes from three interconnected bets:

• Marina Platform: The core system of record. New modules, deeper payments integration, and tools that make Dockwa indispensable to marina operations.
• Boater Products: The demand engine. A consumer app and subscription product that drives bookings, transactions, and loyalty across the network.
• Platform & Intelligence: The future. APIs that partners integrate with, data products that serve insurers and investors, and AI capabilities that optimize everything from pricing to procurement.

You'll own the technical strategy across all three—making the right tradeoffs, sequencing the right bets, and ensuring the architecture supports where we're going, not just where we are.

Scale Payments as Our Growth Engine

Payments isn't a feature at Dockwa—it's the business model. Every module we ship, every marina we onboard, every boater interaction creates payment volume. Your job is to scale this infrastructure: improving reliability, expanding internationally, and building the rails for transaction types we haven't launched yet.

Ship AI That Actually Matters

We're not interested in AI theater. We want AI that drives revenue and operational efficiency—dynamic pricing that optimizes marina yield, analytics that surface actionable insights, automation that eliminates manual work. You'll evaluate opportunities, hire the right talent, and ship products that customers pay for.

Maintain Reliability While Moving Fast

A small team shipping daily requires excellent fundamentals: CI/CD that works, observability that catches problems before customers do, incident response that resolves issues fast. You'll own our security posture and ensure we can grow without fragility.

What we're looking for

You've Built Before

You've scaled an engineering organization in a high-growth environment. You've shipped products that drove real business outcomes, not just technical milestones. You've done this with capital efficiency—getting outsized output without unlimited headcount.

You Have Technical Depth Where It Matters

Payments infrastructure and the complexity of multi-currency, international expansion. Platform architecture and APIs that others build on. Data systems and enough AI fluency to separate real opportunities from hype.

You Lead From the Front

You're a builder who happens to manage people, not a manager who used to build. You set high expectations and hold people accountable. You communicate directly—no corporate-speak, no politics. You're comfortable being player-coach, especially in the early days.

You Thrive in Our Context

Remote-first is how you prefer to work, not a compromise you'll tolerate. Ambiguity energizes you. Vertical SaaS, fintech, or marketplace experience means you understand the dynamics of our business.

How we work

We share this openly so you can evaluate whether Dockwa is the right environment for you. We believe in full transparency during the interview process—not to coach you on what to avoid, but to give you the complete picture.

We are a small team that is winning. Problems grow exponentially with each person, not linearly. We intentionally preserve a lean organization because we want people at the source of problems with clear ownership and autonomy.

We move fast. Context is something we try to give but it doesn't always land perfectly. It's always okay to ask why. Over time, the trust battery goes up.

Everything is solvable. But not everything should be solved. We hate context switching. We'd rather keep people deep in a problem than abandon cart—but we won't chase bad bets for the sake of it.

We have a remarkably good group of humans here. There are no rules or roads where we're going—which makes it damn fun to take the pen and shape the next few turns.

Why now

The marine industry is a backwater—and that's exactly the point. While everyone else chases crowded markets, we're building critical infrastructure for an economy that has no alternative. The incumbents are asleep. The market is ours to take.

You'll work directly with the CEO and a leadership team that has scaled companies before. You'll have the autonomy to make real decisions and the accountability that comes with it. The equity is meaningful because the outcome is large.

If you want to run engineering at a company where you can see the entire system, influence the strategy, and build something that defines a category—this is it.