Director of Finance and Investments

Downtown Toronto, ON – Hybrid

$200,000-$250,000 base plus bonus and excellent benefits

Winchesters is recruiting for a Director of Finance to join a private investment management company in Toronto. Working closely with senior leadership and external advisers, this role offers broad responsibility across investment operations, financial reporting, tax, treasury and real estate finance.

This is an opportunity for a CPA who enjoys a varied, hands-on role within a small, collaborative team. The focus is on the financial and operational execution of investment activity, with investment selection and portfolio strategy led by the investment decision-makers.

Responsibilities

- Oversee finance, compliance and investment operations across corporate and investment entities, including transaction implementation, documentation and coordination with advisers.
- Prepare and oversee financial reporting, investment performance reporting, budgets, forecasts and cash flow models.
- Coordinate tax planning and compliance with external advisers, ensuring accurate records, timely filings and payments, and effective implementation of tax strategies.
- Manage banking relationships, liquidity, intercompany cash movements and foreign exchange,



and negotiate and execute financing arrangements.
- Provide financial oversight for real estate investments and development projects, including modelling, budgeting, cash flow planning and reporting.
- Coordinate legal and governance workstreams, support board reporting, and strengthen financial processes, controls and payment procedures.

Requirements

- CPA designation or equivalent, with training at a Big Four or comparable accounting firm, and a degree in business or finance.
- At least five years of post-qualification industry experience in investment management, wealth management, real estate or a related setting.
- Experience with investments and tax, supported by strong financial reporting, modelling and analytical skills. A current tax-focused role is not required.
- Ability to manage competing priorities, work across a broad range of responsibilities and build effective relationships with senior stakeholders and external advisers.

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

📌 Director of Finance And Administration (Toronto)
🏢 Winchesters
📍 Toronto