Industry: Hospitality (Multi-Property Portfolio) & Real Estate Development
Location: Whitby, ON
Reports To: Chief Executive Officer (CEO)
Position OverviewThe Chief Financial Officer (CFO) is a senior executive responsible for leading the financial strategy, capital structure, investor relations, and operational financial performance of a growing, vertically integrated hospitality and real estate platform.This role oversees multi-property hospitality operations, asset management, real estate development, and investment structures. The CFO will act as a strategic partner to the CEO and executive team, driving profitability, ensuring financial discipline, and leading
capital raising, investor engagement, and funding strategies to support aggressive growth.The ideal candidate brings
deep hospitality experience, along with a proven track record in
investor relations, fundraising, and capital markets execution.
Key Responsibilities1. Strategic Financial Leadership
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Develop and execute financial strategy aligned with organizational growth and expansion objectives
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Serve as a key advisor to the CEO on capital allocation, ROI optimization, and long-term planning
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Lead financial forecasting and modeling (short- and long-term, including 5–10 year projections)
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Support acquisitions, new developments, and phased property openings
2. Multi-Property & Hospitality Operations Finance
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Oversee financial performance across all hospitality assets using USALI standards
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Monitor and optimize key metrics including ADR, RevPAR, occupancy, GOP, and EBITDA
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Standardize financial reporting, KPIs, and dashboards across all properties
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Partner with operations teams to improve margins and drive cost efficiencies
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Implement cost control frameworks (labour ratios, COGS, departmental profitability)
3. Real Estate Development & Project Finance
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Lead financial structuring of development projects, renovations, and repositioning initiatives
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Manage development budgets, capital expenditures, and lender reporting
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Conduct feasibility studies and sensitivity analyses (occupancy, ADR, cost variables)
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Collaborate with construction, design, and project management teams
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Ensure projects are delivered on budget and aligned with pro forma returns
4. Capital Markets & Fundraising
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Lead all capital raising activities, including debt and equity financing (senior, mezzanine, LP/GP structures, syndications)
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Develop and execute fundraising strategies to support acquisitions, developments, and platform growth
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Build and manage relationships with banks, private lenders, institutional investors, and capital partners
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Own investor relations, including:
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Investor communications and reporting
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Quarterly performance updates
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Return metrics (IRR, equity multiples)
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Support structuring and scaling of investment vehicles and partnership models
5. Treasury & Cash Flow Management
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Oversee cash flow, liquidity, and working capital across multiple entities
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Optimize capital allocation and debt servicing strategies
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Manage intercompany transactions and fund flows between operating, development, and investment entities
6. Financial Reporting, Compliance & Controls
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Ensure accurate, timely financial reporting (monthly, quarterly, annual)
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Maintain compliance with accounting standards (ASPE/IFRS), tax regulations, and industry requirements
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Oversee audits, internal controls, and risk management frameworks
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Liaise with external auditors, financial institutions, and stakeholders
7. Systems, Data & Process Optimization
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Implement and scale financial systems (ERP, PMS, accounting platforms)
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Build integrated financial infrastructure and real-time reporting dashboards
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Establish standardized processes for budgeting, forecasting, and reporting
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Drive automation, data accuracy, and operational efficiency
8. Team Leadership & Cross-Functional Partnership
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Build and lead a high-performing finance team (controllers, property accountants, FP&A)
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Establish SOPs for financial operations and reporting cycles
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Partner with operations, sales, and development teams to drive accountability and performance
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Foster a culture of financial discipline and continuous improvement
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EBITDA and GOP margin performance
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Accuracy of forecasts vs. actual results
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Development projects delivered within budget (±5%)
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Cash flow stability and liquidity metrics
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Debt service coverage ratios (DSCR)
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Investor return metrics (IRR, equity multiples)
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Success of capital raising and funding initiatives
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10+ years of progressive finance leadership experience (CFO, VP Finance, or equivalent)
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Strong hospitality experience (hotels, resorts, or multi-property operations)
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Proven experience in investor relations and capital raising / fundraising
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Demonstrated success managing multi-entity or multi-property financial operations
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Experience in real estate development, project finance, and structured financing
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Deep understanding of hospitality KPIs (ADR, RevPAR, occupancy, etc.)
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Advanced financial modeling, forecasting, and investment analysis
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Experience with ERP systems, PMS platforms, and financial reporting tools
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Strong knowledge of accounting standards (IFRS/ASPE) and regulatory compliance
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Strategic thinker with strong business and investment acumen
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Hands-on leader comfortable operating at both strategic and operational levels
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Excellent communication and stakeholder management skills
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High level of integrity, accountability, and attention to detail
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CPA, CFA, or equivalent designation
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Experience in high-growth or private equity-backed environments
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Background in acquisitions, integrations, or portfolio expansion
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Base Salary: $150,000 – $190,000
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Performance Bonus: 10–40%+ (tied to growth, capital raising, and financial performance)
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Total Compensation: ~$190,000 – $300,000+
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Long-term incentives (phantom equity / profit-sharing)
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Comprehensive benefits package
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Step into a true CFO role with ownership over strategy, capital, and growth
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Lead fundraising, investor relationships, and deal execution
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Build and lead finance across a growing hospitality and development platform
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Work directly with ownership on strategy, capital, and expansion
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Join a high-growth environment with strong upside potential
Cottage Dream Vacations is committed to an inclusive, barrier-free recruitment and selection process. If you require an accommodation at any stage of the hiring process, please let us know and we will work with you to meet your needs. 