Industry: Hospitality (Multi-Property Portfolio) & Real Estate Development
Location: Whitby, ON
Reports To: Chief Executive Officer (CEO)
Position Overview
The Chief Financial Officer (CFO) is a senior executive responsible for leading the financial strategy, capital structure, 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 supporting expansion through acquisitions, development projects, and structured financing.
The ideal candidate combines deep hospitality finance expertise with strong experience in real estate development, capital markets, and multi-entity financial management.
Key Responsibilities
1. Strategic Financial Leadership
- Develop and execute financial strategy aligned with organizational growth and expansion objectives
- Serve as a key advisor to the CEO on capital allocation, ROI optimization, and long-term planning
- Lead financial forecasting and modeling (short- and long-term, including 5–10 year projections)
- Support acquisitions, new developments, and phased property openings
2. Multi-Property & Hospitality Operations Finance
- Oversee financial performance across all hospitality assets using USALI standards
- Monitor and optimize key metrics including ADR, RevPAR, occupancy, GOP, and EBITDA
- Standardize financial reporting, KPIs, and dashboards across all properties
- Partner with operations teams to improve margins and drive cost efficiencies
- Implement cost control frameworks (labour ratios, COGS, departmental profitability)
3. Real Estate Development & Project Finance
- Lead financial structuring of development projects, renovations, and repositioning initiatives
- Manage development budgets, capital expenditures, and lender reporting
- Conduct feasibility studies and sensitivity analyses (occupancy, ADR, cost variables)
- Collaborate with construction, design, and project management teams
- Ensure projects are delivered on budget and aligned with pro forma returns
4. Capital Markets & Fundraising
- Structure and manage debt and equity financing (senior, mezzanine, construction loans, LP/GP structures)
- Lead capital raising initiatives for acquisitions, developments, and platform growth
- Maintain relationships with banks, lenders, and institutional investors
- Oversee investor reporting, including IRR, equity multiples, and performance updates
5. Treasury & Cash Flow Management
- Manage cash flow, liquidity, and working capital across multiple entities
- Optimize capital allocation and debt servicing strategies
- Oversee intercompany transactions and fund flows across operating and investment entities
6. Financial Reporting, Compliance & Controls
- Ensure accurate, timely financial reporting (monthly, quarterly, annual)
- Maintain compliance with accounting standards (ASPE/IFRS), tax regulations, and industry requirements
- Oversee audits, internal controls, and risk management frameworks
- Liaise with external auditors, financial institutions, and stakeholders
7. Systems, Data & Process Optimization
- Implement and scale financial systems (ERP, PMS, accounting platforms)
- Build integrated financial infrastructure and real-time reporting dashboards
- Establish standardized processes for budgeting, forecasting, and reporting
- Drive automation, data accuracy, and operational efficiency
8. Team Leadership & Cross-Functional Partnership
- Build and lead a high-performing finance team (controllers, property accountants, FP&A)
- Establish SOPs for financial operations and reporting cycles
- Partner with operations, sales, and development teams to drive accountability and performance
- Foster a culture of financial discipline and continuous improvement
Key Performance Indicators (KPIs)
- EBITDA and GOP margin performance
- Accuracy of forecasts vs. actual results
- Development projects delivered within budget (±5%)
- Cash flow stability and liquidity metrics
- Debt service coverage ratios (DSCR)
- Investor returns (IRR, equity multiples)
- Operational cost efficiencies and margin improvements
Experience
- 10+ years of progressive finance leadership experience (CFO, VP Finance, or equivalent)
- Strong background in hospitality (hotels, resorts, or multi-property operations)
- Experience in real estate development and project finance
- Proven ability to manage multi-entity or multi-property financial operations
- Experience with capital raising, financing structures, and investor relations
Technical Skills
- Deep understanding of hospitality KPIs (ADR, RevPAR, occupancy, etc.)
- Advanced financial modeling, forecasting, and analysis capabilities
- Experience with ERP systems, PMS platforms, and financial reporting tools
- Strong knowledge of accounting standards (GAAP/IFRS/ASPE) and compliance
Leadership & Attributes
- Strategic thinker with strong business and investment acumen
- Hands-on leader comfortable operating at both strategic and operational levels
- Excellent communication and stakeholder management skills
- High level of integrity, accountability, and attention to detail
Preferred
- CPA, CFA, or equivalent designation
- Experience in high-growth or private equity-backed environments
- Background in acquisitions, integrations, or portfolio expansion
Compensation & Benefits
- Base Salary: $150,000 – $190,000
- Performance Bonus:
- 10–25% (initial phase)
- Scaling to 20–40% with portfolio growth
- Total Compensation: ~$190,000 – $300,000+
- Long-term incentives (phantom equity / profit-sharing)
- Comprehensive benefits package
- Clear path to increased compensation as portfolio expands
Why Join Us?
- Step into a true CFO role with significant ownership and influence
- Build and lead finance across a growing hospitality and development platform
- Work directly with ownership on strategy, capital, and expansion
- 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.
Job Types: Full-time, Permanent
Pay: $150,000.00-$190,000.00 per year
Benefits:
- Casual dress
- Company events
- Dental care
- Extended health care
- On-site parking
- Paid time off
- Vision care
Work Location: In person
