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

www.CottageDreamVacations.com

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