Product Manager- Business Systems

Del Mar Vacations is a Veteran-owned and operated, full-service vacation property management company with over 400 homes across Cape Cod. Our mission is to create lifelong memories through 5-star guest and homeowner experiences—and we do that by putting hospitality and service at the heart of everything we do.

We’re a team of passionate, smart, and engaged people who solve problems creatively and serve with care. Our ideal teammates thrive in a high-energy, tight-knit environment, are intellectually curious, optimistic, and ready to pivot when things change.

We live and work by our mantra:
R.R.R.E.E.E. – Readiness. Responsiveness. Resolution. Empathy. Efficiency. Enthusiasm. It’s how we show up, how we fix things, and how we treat people.

Our values make this more than just a job:

• Be Reliable. Reliable. Reliable.
• Think like a Guest. Think like a Homeowner. Think like a Team Member.
• The Obstacle is the Opportunity.
• Make it Happen.
• Be Anti-Fragile.

If that resonates with you, keep reading.

Salary Range: $120,000–$150,000+ base (depending on experience) + generous performance bonus

Del Mar Vacations is a veteran-owned, full-service vacation rental company with 400 homes across Cape Cod. We create lifelong memories through 5-star guest and homeowner experiences by putting hospitality and service at the center of everything we do. Our team is high-energy, curious, and hands-on — we live by R.R.R.E.E.E. (Readiness. Responsiveness. Resolution. Empathy. Efficiency. Enthusiasm.) and values like “Be Reliable” and “The Obstacle is the Opportunity.”

This role requires being onsite on Cape Cod frequently to observe real workflows, build trust, and drive adoption across teams.
The expectation: 3 days/week onsite in our Cape Cod office. Candidates based off-Cape are encouraged to apply just if you’re truly willing to commute.

We need a senior Product Manager who executes the CTFO + CEO’s platform vision by optimizing how people actually use our systems — so data is clean, workflows are reliable, and outcomes happen.

This is a current-state product role as much as a future roadmap role. Our biggest platform problems aren’t “lack of features” — they’re data quality, inconsistent user behavior, unclear requirements, and process drift that create rework, escalations, and wasted time. You’ll take messy operational reality and turn it into simple, reliable workflows, integrations, and AI automations.

You’ll drive accountability end-to-end: definition → build → QA → rollout → adoption → measured impact.
We are NOT hiring a theorist, and we are NOT looking to replatform. We want an operator-PM who makes the systems work and proves it with outcomes.

Own the end-to-end improvement of how Del Mar teams use our platform—so data is clean, workflows are reliable, and outcomes actually happen. You’ll observe real user behavior across departments, turn friction into clear specs and prioritized work, and drive new tech / products from definition → build → QA → rollout → adoption.

You’ll be hands-on in Hub Spot and across our system stack (Guesty, Zuper, Zapier, custom guest and owner portals, pricing/marketing tools). Your north star is simple:
less wasted effort, fewer escalations, better decisions, better service for our customers, and smarter work for our team members.

You’ll report to our Chief Technology & Finance Officer, Colin, and work closely with the CEO and functional directors. You’ll own product delivery for the business systems that run the company — and you’ll be the person teams call when systems need to actually work (not just look pretty in a diagram).

Every week, you will repeat this loop like a professional menace to chaos (we think…)

• Observe users
• Fix workflow + data
• Ship improvements
• Measure outcomes

• Shadow teams across Ops, Marketing, Owner Revenue, Guest Revenue, + Guest Experience
• Map processes, workflows, find friction, reduce variance, and eliminate rework
• Fix forms and data capture so information is…