Financial Controller

Del Mar Vacations • Orleans, MA

6d • $85,000 - $120,000 • Hybrid

About The Position

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.

Requirements

• 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

Responsibilities

• 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: QuickBooks Online, Divvy, Guesty, HubSpot, 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 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 1-10 employees