Financial Controller Job Orleans Massachusetts USA,Finance & Banking

Location: Orleans

About Del Mar Vacations

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.

Who We Are

Del Mar Vacations is a Veteran-owned, full-service vacation rental company managing 400+ homes across Cape Cod. Our mission is to create lifelong memories through 5-star guest and homeowner experiences, powered by a team that moves fast, solves problems, and cares a lot.

We live by: R.R.R.E.E.E. — Readiness, Responsiveness, Resolution, Empathy, Efficiency, Enthusiasm

And we’re serious about our values:

Be Reliable. Reliable. Reliable.

Think like a Guest / Homeowner / Team Member

The Obstacle is the Opportunity

Make it Happen

Be Anti-Fragile

If you like building structure inside chaos (without becoming the chaos), you’ll fit in.

The Role:

Controller

Salary range: $85,000-$120,000

We’re hiring a Controller who can run the core accounting engine and operate as a strategic right hand to Colin, our Chief Technology and Finance, Colin. This is not a “keep the books tidy” job. This is build the machine:
clean close, strong controls, sharp reporting, confident cash visibility, and finance workflows that scale as we grow. This role is based in Orleans, MA with hybrid flexibility—candidates must be local to Cape Cod or the South Shore.

You’ll work closely with our CFO (Colin), COO (Vanessa), and CEO (Luke), internal accounting team, and outsourced finance partners. You’ll bridge the gap between day-to-day accounting execution and executive-level financial clarity.

Bottom line: you’ll make the financials trustworthy, timely, and useful—so leadership can make better decisions faster.

What You’ll Own (Core Accountabilities)

Close, Controls, and Financial Integrity (The “No Surprises” Engine) Own the monthly close end-to-end: schedule, checklist, reconciliations, review, and final outputs. Ensure clean revenue recognition, accruals, prepaid schedules, and balance sheet hygiene. Build and maintain internal controls to reduce fraud, error, leakage, and “mystery money.” Keep us audit-ready all year, not just when someone’s panicking in March.

CFO-Level Reporting + Decision Support (Make the Numbers Mean Something) Produce monthly financial package (P&L, balance sheet, cash flow, KPIs, variance explanations). Deliver spend visibility and trend insights: what’s changing, why, and what we should do about it. Partner with Colin on forecasting, budget vs. actual analysis, and leadership-ready reporting. Translate financial results into clear “here’s what it means” narratives for execs and department leaders.

Cash, Working Capital, and Process Scale (Finance Ops That Don’t Break) Own cash visibility: near-term cash planning + systems to prevent surprises. Oversee A/P and A/R workflow health: accuracy, timing, approvals, and controls. Improve working capital rhythms (billing discipline, collections, payout timing, vendor terms). Build scalable workflows across systems:
Quick Books Online, Divvy, Guesty, Hub Spot, Zuper (and whatever else reality throws at us).

Tax and Compliance Coordination (Boring, Necessary, Must Be Excellent) Coordinate tax filings, forms, and payments with external partners. Maintain documentation and schedules so compliance is routine—not a last-minute ritual sacrifice.

Systems + Team Enablement (Make…


Increase/decrease your Search Radius (miles)



Job Posting Language