Director of Finance

About Us

We are an entrepreneurial group of companies operating across real estate, hospitality, manufacturing, wellness, education, and consumer products. Our portfolio continues to grow through acquisition, development, and innovation, creating exciting opportunities and unique financial complexity.

As our organization expands, we are looking for an experienced Director of Finance who is energized by bringing structure, consistency, and financial discipline to a dynamic multi-company environment. This is an opportunity to build—not simply maintain. You'll play a pivotal role in creating scalable financial processes, standardizing reporting across multiple operating companies, and establishing the systems and controls that will support our next phase of growth.

We're seeking someone who enjoys building strong financial foundations in entrepreneurial organizations. You'll thrive if you're naturally curious, enjoy solving complex operational challenges, and have a proven ability to simplify complexity while supporting business leaders with clear, actionable financial insights.

Reporting directly to the executive leadership team, you'll work closely with leaders across our operating companies to improve financial visibility, strengthen processes, and help drive strategic decision-making. This role requires someone who is equally comfortable developing long- term financial strategy as they are rolling up their sleeves to improve day-to- day operations.

This is a fully in-office leadership position based at our Whitby headquarters (4 Cannon Court), where you'll collaborate closely with our executive team and play an integral role in shaping the future of our growing organization.

The Opportunity

The Director of Finance will lead all finance and accounting operations across multiple operating companies. Reporting directly to the President and executive leadership team, you will establish strong financial controls, improve reporting accuracy, streamline accounting processes, and provide the financial insight necessary for strategic decision making.

The successful candidate has experience walking into organizations where accounting processes, reporting, and controls require improvement and has successfully implemented systems that create clarity, accountability, and scalable growth.

This role requires both strategic thinking and hands-on execution.

What You'll Be Responsible For

Financial Leadership

• Lead the finance function across multiple operating companies.
• Oversee monthly, quarterly, and annual financial reporting.
• Ensure accurate and timely financial statements for each entity.
• Develop meaningful KPI dashboards for executives.
• Deliver actionable financial analysis to support strategic decisions.

Multi-Company Financial Management

• Manage consolidated reporting across numerous legal entities.
• Ensure intercompany transactions are properly recorded and reconciled.
• Improve consistency of accounting practices across all operating companies.
• Develop standardized financial reporting packages for leadership.

Financial Turnaround & Process Improvement

• Assess current accounting workflows and identify operational inefficiencies.
• Design and implement improved financial processes and internal controls.
• Modernize reporting systems and eliminate manual inefficiencies.
• Build scalable accounting procedures that support future growth.
• Improve month-end close timelines and reporting accuracy.
• Lead finance transformation initiatives from planning through implementation.

Budgeting & Forecasting

• Lead annual budgeting across all business units.
• Develop rolling forecasts and cash flow projections.
• Monitor business performance against budgets.
• Recommend corrective actions when financial performance deviates from plan.

Cash Flow & Treasury

• Manage organizational cash flow.
• Optimize working capital.
• Monitor banking relationships and financing arrangements.
• Ensure appropriate liquidity across all operating companies.

Leadership

• Lead, mentor and develop the accounting and finance team.
• Establish clear accountability and performance expectations.
• Foster a culture of continuous improvement and ownership.

Compliance

• Ensure compliance with Canadian accounting standards and applicable tax regulations.
• Coordinate annual reviews, audits and external accounting relationships.
• Oversee corporate tax filings and regulatory reporting.
• Strengthen internal controls and risk management practices.

What We're Looking For

Required Experience

• CPA designation (required).
• 10+ years of progressive finance leadership experience.
• Minimum 5 years leading finance teams.
• Demonstrated experience supporting multiple operating companies simultaneously.
• Proven success entering organizations that required significant financial process improvements or operational turnaround.
• Experience implementing financial controls and improving reporting accuracy.
• Strong budgeting, forecasting, cash flow, and financial planning experience.
• Experience leading ERP, accounting system, or finance process improvements.
• Advanced Excel and financial modeling skills.

Preferred Experience

Experience in one or more of the following industries is considered an asset:

• Hospitality
• Real Estate
• Property Management
• Consumer Products
• Retail
• Education
• Multi-entity corporate environments

The Ideal Candidate

You are someone who enjoys creating order out of complexity. You don't simply maintain finance departments—you improve them.

You ask questions, identify root causes, and implement lasting solutions. You're comfortable working with entrepreneurs, adapting quickly to changing priorities, and balancing strategic leadership with hands-on execution.

You have a strong operational mindset and believe finance should help drive the business—not simply report on it.

Success in the First 12 Months

The successful candidate will:

• Improve month-end reporting timelines.
• Standardize financial reporting across all operating companies.
• Strengthen internal controls and financial governance.
• Build executive dashboards with meaningful KPIs.
• Improve forecasting accuracy and cash flow visibility.
• Establish consistent budgeting processes.
• Increase confidence in financial reporting across the leadership team.
• Create scalable finance processes capable of supporting continued business growth.

Why Join Us?

• Opportunity to make a significant impact across multiple growing businesses.
• Work directly with entrepreneurial leadership.
• Lead transformational finance initiatives.
• Diverse portfolio of industries and operating companies.
• Comprehensive benefits package.
• Stable, long-term leadership opportunity with room for growth.

If you're energized by improving businesses, building strong financial foundations, and leading change across multiple operating companies, we'd love to hear from you.

Cottage Dream Vacations is committed to providing an inclusive recruitment process. Accommodation requests can be made at any stage of the hiring process.