About the Role:

We’re hiring a Controller who can run the core accounting engine and operate as a strategic right hand to our Chief Technology and Finance Officer. 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), our 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.

Core Responsibilities 

Drive the execution and performance of Del Mar's financial engine — delivering clean reporting, strong controls, and the cash visibility that empowers leadership to make confident decisions.

Close, Controls, and Financial Integrity

• 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 financial surprises
• Keep us audit-ready all year, not just when someone’s panicking in March

CFO-Level Reporting and Decision Support

• 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 the CFO on forecasting, budget vs. actual analysis, and leadership-ready reporting
• Translate financial results into clear narratives for executives and department leaders

Cash, Working Capital, and Process Scale

• Own cash visibility: near-term cash planning and 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

Tax and Compliance Coordination

• Coordinate tax filings, forms, and payments with external partners
• Maintain documentation and schedules so compliance is routine—not a last-minute ritual

Systems and Team Enablement

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

Qualifications

• Bachelor’s degree in Accounting; CPA preferred
• 7+ years in accounting/finance with progressive responsibility; public and private background preferred
• Experience in high-transaction environments (hospitality, property management, marketplace models) preferred
• Strong QuickBooks Online experience in a real operational environment
• Ability to run close and controls, and also support forecasting, cash planning, and exec reporting
• Clear communicator—no finance fog machine, no vague hand-waving
• Love building systems, tightening processes, and making messy things make sense
• Process improvement, automation, or experience building finance ops from scratch

Why Join the Del Mar Vacations Team

Del Mar Vacations is a Veteran-owned and operated, full-service vacation rental company on Cape Cod. We specialize in providing 5-star experiences to our guests, homeowners and each other. As a hospitality and service first culture, our team and their talents are the key to our success.

Working at Del Mar means you will be surrounded by passionate, smart, and engaged people who are focused on superior problem solving and outstanding customer service. Our ideal candidates enjoy working in a small, tight-knit, high energy and supportive team, are intellectually curious, comfortable with ambiguity, have a positive outlook, and are able to pivot quickly as things change. 

Benefits

• 2 weeks of vacation time
• 1 week of sick time
• Partially subsidized health insurance
• HSA (health savings account)
• 401k with up to 4% match
• Professional development opportunities
• Yearly bonus program (and other rewards and recognition both big and small)

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

Schedule: Full time, Monday-Friday, Occasional Weekends

Del Mar Vacation, Inc is an equal opportunity employer. All employment will be decided solely on the basis of your qualifications and merit and according to hiring needs. We are committed to creating a collaborative team and do not to discriminate based off  race, color, religion, creed, gender, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, amnesty, status as a covered veteran, military service, or any other class protected by applicable federal, state, and local law