Build the Finance Function for a Growing Group of Companies
We 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 Own
Financial 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 clear 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 For
You 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 and 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 Like
During 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 prospect 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.
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📌 VP of Finance | Multi-Company / Real Estate & Hospitality (Ontario)
🏢 Cottage Dream Vacations
📍 Ontario