Director of Finance And Administration

Toronto, ON
Hybrid
Posted Oct 15, 2026
1 position

$200,000–$250,000 / year

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Employment type: Full-time
Experience level: Senior · 5+ years
Minimum education: Professional degree
Posting language: English
Working hours: 40 hours per week
Seniority: Director
Application method: Direct apply is available

Job summary

Oversee finance, compliance, and investment operations across corporate and investment entities, including reporting, budgeting, forecasting, tax coordination, treasury, and financing. Provide financial oversight for real estate investments and development projects, coordinate legal and governance work, support board reporting, and strengthen financial processes and controls.

Job details

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 environment. 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.

What you’ll do

Requirements

Requires a CPA or equivalent, training at a Big Four or comparable accounting firm, and a degree in business or finance. Candidates need at least five years of post-qualification industry experience in investment management, wealth management, real estate, or a related field, along with investment and tax experience, strong financial and analytical skills, and the ability to manage competing priorities and work with senior stakeholders and external advisers.