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)

1) 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

2) 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

3) 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: QuickBooks Online, Divvy, Guesty, HubSpot, Zuper (and whatever else reality throws at us)

4) 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

5) Systems + Team Enablement (Make Everyone Better)

• Optimize our accounting tech stack and SOPs (standard operating procedures)
  
  
  
• Create clarity across departments on coding, purchasing, approvals, and accountability
• You'll lead our 2-person accounting team and partner with outsourced finance resources.

What Success Looks Like (First 90–180 Days)

By Day 30:

• Get to know Del Mar’s business
• Close calendar in place, ID bottlenecks and quick wins
• Clear view of top problem accounts/workflows + plan to fix

By Day 90:

• Close running on-time with fewer surprises
• Monthly financial package is reliable, readable, and delivered fast
• Controls tightened around spend, approvals, and account reconciliations

By Day 180:

• Forecasting and cash visibility materially improved
• Finance workflows documented + scalable
• Leadership trusts the numbers and uses them to run the business

You Might Be a Fit If You…

• Have a Bachelor’s in Accounting (CPA preferred—equivalent experience welcomed)
• Have experience in high-transaction environments (hospitality, property management, marketplace models) is strongly preferred—this isn't a simple single-entity business.
• Bring 7+ years in accounting/finance with progressive responsibility (public + private a bonus)
• Have strong QuickBooks Online experience in a real operational environment (not just a clean SaaS demo)
• Know how to run close + controls, and you can also support forecasting, cash planning, and exec reporting
• Communicate clearly—no finance fog machine, no vague hand-waving
• Love building systems, tightening processes, and making messy things make sense
• Can lead with ownership and still play nicely with others (rare, precious, hire them)

• Process improvement, automation, or building finance ops from scratch

What’s In It For You

• 75% employer-paid health insurance (including dependents) + dental/vision + HSA
• Interesting work–every day
• 401(k) with up to 4% match
• PTO + sick time + bonus program + recognition rewards
• Professional development support (yes, real support)
• Hybrid/remote flexibility
• A real chance to help build a world-class finance function—not just maintain one
• Fun, high-accountability team that actually likes each other
  
  
  

📩 Ready to bring order, strategy, and confidence to Del Mar’s financial engine? Apply now.