Build the Finance Function for a Growing Group of CompaniesWe are looking for a hands-on Director of Finance to lead and strengthen the finance function across a growing portfolio of operating companies.Our businesses span hospitality, real estate, manufacturing, wellness, education and consumer products.

That diversity creates an interesting challenge: multiple entities, different operating models and a growing need for consistent financial reporting, controls, forecasting and decision support.This is not a role for someone who simply wants to maintain an established finance department.We need a CPA who enjoys creating order from complexity—someone who can quickly understand how the businesses operate, identify what's working and what isn't, and build the financial processes, reporting and controls required for continued growth.You'll work directly with the President and leadership team and have the opportunity to make a visible impact across the organization.

What You'll OwnFinancial Leadership & Reporting

- Lead finance and accounting across multiple operating companies
- Own monthly, quarterly and annual financial reporting
- Improve the accuracy and timeliness of financial statements
- Build standardized reporting packages and executive KPI dashboards
- Translate financial results into clear recommendations for leadership

Finance Transformation
- Assess existing accounting processes, controls and workflows
- Identify gaps, inefficiencies and opportunities for automation
- Improve month-end close processes and reporting timelines
- Standardize accounting practices across operating companies
- Lead improvements to accounting systems, ERP tools and financial processes
- Build scalable processes that can support continued growth

Planning, Forecasting & Cash Flow




- Lead annual budgeting and rolling forecasts
- Develop cash flow forecasts and improve liquidity visibility
- Monitor performance against plan and identify emerging risks and opportunities
- Optimize working capital and support banking and financing relationships
- Help leadership make better decisions using forward-looking financial analysis

Team & Controls
- Lead, coach and develop the accounting and finance team
- Establish transparent ownership, accountability and performance expectations
- Strengthen internal controls and financial governance
- Coordinate external accountants, annual reviews/audits, tax filings and regulatory reporting

What We're Looking ForYou should bring:

- CPA designation
- 8+ years of progressive accounting and finance experience
- Experience leading or developing finance/accounting teams
- Strong financial reporting, budgeting, forecasting and cash-flow management experience
- Experience working across multiple companies, business units or legal entities
- A track record of improving accounting processes, controls or reporting
- Strong Excel and financial modelling skills
- Experience improving an ERP, accounting system or finance workflow
- The ability to move comfortably between strategic discussions and hands-on problem solving

Experience in hospitality, real estate, property management, consumer products, retail,



education or another multi-entity environment is an asset, but not required.

You'll Thrive Here If...You're naturally curious and don't accept "that's how we've always done it" as an answer.You enjoy digging into a business, understanding the numbers behind its operations and finding practical ways to make things work better.You're comfortable in an entrepreneurial environment where priorities can evolve quickly. You can establish structure without creating unnecessary bureaucracy, and you're equally comfortable presenting to leadership and rolling up your sleeves to solve an accounting problem.Most importantly, you believe finance should help drive the business—not simply report on it.

What Success Looks LikeDuring your first year, you'll help us:

- Shorten and strengthen the month-end close
- Standardize reporting across our operating companies
- Improve financial controls and governance
- Give leadership better KPI and performance visibility
- Improve forecasting and cash-flow visibility
- Establish consistent budgeting processes
- Increase confidence in our financial information
- Build a finance function capable of supporting continued growth

Why Join Us?This is an opportunity to have a meaningful impact rather than inherit a narrowly defined corporate role.You'll work directly with entrepreneurial leadership, gain exposure to businesses across several industries, and have the mandate to improve how finance operates across the organization.If you've ever looked at a finance function and thought, "I know how to make this better," we'd like to meet you.Cottage Dream Vacations is committed to providing an inclusive recruitment process. Accommodation requests can be made at any stage of the hiring process.

📌 Director of Finance | Multi-Company / Real Estate & Hospitality (Whitby)
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