Chief Financial Officer (CFO), Whitby

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, 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 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

Lead all

capital raising activities , including debt and equity financing (senior, mezzanine, LP/GP structures, syndications)

Develop and execute

fundraising strategies

to support acquisitions, developments, and platform growth

Build and manage relationships with

banks, private lenders, institutional investors, and capital partners

Own investor relations, including:

Investor communications and reporting

Quarterly performance updates

Return metrics (IRR, equity multiples)

Support structuring and scaling of

investment vehicles and partnership models

5. Treasury&Cash Flow Management

Oversee cash flow, liquidity, and working capital across multiple entities

Optimize capital allocation and debt servicing strategies

Manage intercompany transactions and fund flows between operating, development, 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 return metrics (IRR, equity multiples)

Success of capital raising and funding initiatives

Experience

10+ years of progressive finance leadership experience (CFO, VP Finance, or equivalent)

Strong hospitality experience

(hotels, resorts, or multi‑property operations)

Proven experience in investor relations and capital raising / fundraising

Demonstrated success managing

multi‑entity or multi‑property financial operations

Experience in

real estate development, project finance, and structured financing

Technical Skills

Deep understanding of hospitality KPIs (ADR, RevPAR, occupancy, etc.)

Advanced financial modeling, forecasting, and investment analysis

Experience with ERP systems, PMS platforms, and financial reporting tools

Strong knowledge of accounting standards (IFRS/ASPE) and regulatory 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:

10–40%+ (tied to growth, capital raising, and financial performance)

Total Compensation:

~$190,000– $300,000+

Long‑term incentives (phantom equity / profit sharing)

Comprehensive benefits package

Why Join Us?

Step into a true CFO role with ownership over

strategy, capital, and growth

Lead

fundraising, investor relationships, and deal execution

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.

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