Top Benefits
About the role
Location:
22 St. Clair Avenue East, Toronto, Ontario, M4T 2S7
About Us
Wittington Investments, Limited, a private Canadian company, is the holding company of the Weston group of companies, which includes George Weston Limited, Loblaw Companies Limited and Choice Properties REIT.
George Weston Limited is a Canadian public company, founded in 1882. George Weston has two operating segments: Loblaw Companies Limited, Canada’s largest food and drug retailer and a provider of financial services, and Choice Properties Real Estate Investment Trust, Canada’s largest and preeminent diversified REIT. With over 200,000 employees working at George Weston and its operating segments, the group of companies represent one of Canada’s largest private sector employers.
Job Description
About Us:
Wittington is a purpose-driven holding company that stewards the Weston family’s investments and philanthropic legacy. As the controlling shareholder of George Weston Limited - and through it, Loblaw and Choice Properties - we manage a global portfolio and support transformative initiatives across Canada. Wittington is also the home to charitable foundations that include the Weston Family Foundation and The Hilary and Galen Weston Foundation, which help advance Wittington’s philanthropic ambitions.
Our corporate values are the foundation of everything we do — guiding our decisions, shaping our culture, and defining how we succeed together.
- Integrity - We lead with integrity and humility
- Professionalism - We invest and serve with courage and excellence
- Long-term thinking - We prioritize long-term thinking and outcomes over short-term fixes and outputs
- Contributing - We believe that our greatest strength lies in our people, our culture and our shared purpose
The Opportunity:
As Senior Director, Investment Operations, you will be a senior leader responsible for the operational infrastructure, reporting accuracy, valuation processes, and treasury management that support Wittington’s diversified investment portfolio and the venture fund. This role blends strategic oversight with hands-on execution, ensuring that operations run seamlessly, valuations are rigorous and defensible, reporting is timely and insightful, and treasury functions maximize liquidity and capital efficiency. The role reports to the VP Finance and Treasury, who will mentor you to grow with the Company, challenge you to take on increasing levels of responsibility, innovate continuously, and develop your leadership abilities.
Key Job Responsibilities:
- Investment Operations
- Oversee trade execution, capital calls/distributions, settlement, and reconciliation across a multi-asset-class portfolio.
- Ensure portfolio data integrity, investment accounting accuracy, and timely close processes in coordination with finance teams and external administrators.
- Implement and maintain robust operational controls and governance frameworks.
- Ensure compliance with investment policies and procedures, including documentation, benchmarking, and custodian coordination.
- Investment Reporting
- Lead preparation of recurring and ad hoc investment performance reports, portfolio analytics, and exposure summaries for leadership, boards, and other stakeholders.
- Oversee the maintenance and improvement of investment systems (e.g., Northern Trust FOS) to enhance reporting flexibility and performance tracking.
- Ensure investment reports are created based on industry standards and completed and distributed with high quality and within the expected timelines.
- Build and enhance dashboards and reporting tools that deliver clear, actionable insights.
- Collaborate with investment teams to provide both qualitative and quantitative portfolio analysis for strategic decisions.
- Develop an ongoing working relationship with Investment and Finance colleagues to understand strategies, policies, and transactions as they pertain to performance measurement and other reporting.
- Valuation
- Oversee and manage the valuation process for all investments, including private equity, private funds, real estate, credit, and other assets.
- Develop and maintain valuation policies and procedures in compliance with accounting standards and industry best practices.
- Coordinate with investment teams, finance, auditors, and third-party valuation specialists to ensure accurate and timely valuations.
- Present and defend valuations to internal and external stakeholders as required.
- Treasury Management
- Direct daily treasury operations, including cash flow forecasting, liquidity management, payment processing, and banking relationships.
- Implement financing strategies and manage financial risks (e.g. FX, interest rate exposure).
- Ensure compliance with treasury-related regulatory requirements and internal controls, including segregation of duties and credit risk protocols.
- Lead automation and dashboard development to streamline treasury reporting and insights.
- Strategic & Leadership Contributions
- Support strategic decisions through financial insights on capital budgeting, investment strategies, and risk management.
- Partner with leadership to align operations, valuation, reporting, and treasury strategy with overall business objectives.
- Drive continuous improvement through technology adoption and process enhancements across investment and treasury functions.
- Stay abreast of industry standards and best practices while continuously seeking opportunities to enhance operational efficiency and mitigate operational risks
- Foster a culture of accountability, innovation, and professional development.
- Other ad-hoc duties as required.
Qualifications & Experience:
- Bachelor’s degree in Finance, Accounting, Economics, or related field required; MBA, CFA, or CPA strongly preferred.
- 10+ years of progressive leadership in investment operations, investment reporting and valuation within a private investment company, asset management firm, family office, or institutional investment environment.
- Deep knowledge of investment structures, fund administration, custody, and performance measurement.
- In-depth technical expertise in valuation methodologies for private and illiquid assets, including DCF, market comparables, and third-party appraisal processes.
- Proven ability to deliver accurate, board-ready investment reporting and defend valuations.
- Advanced treasury skills, including liquidity optimization, capital planning, and FX risk management.
- Proficiency with portfolio management systems, BI/reporting tools, and advanced Excel/data modeling.
- Strong governance and control mindset with experience building and enforcing operational and valuation policies.
- Exceptional communication, stakeholder management, and presentation skills.
- Ability to operate in a fast-paced environment with numerous competing priorities and reporting deadlines.
- Exceptional interpersonal skills with a proven ability to build trusting relationships at all levels of the organization.
- Strong team player with excellent problem-solving, communication, and client service skills, as well as the ability to take ownership and manage projects.
What We Offer:
- A friendly, collaborative, and inclusive culture
- A total rewards package that includes competitive compensation, flexible benefits as well as pension and investment plans
- Tuition reimbursement and training to help you reach your full potential
- Wellness programs and initiatives
Wittington is an equal opportunity employer committed to promoting a diverse and inclusive workplace. We know our success depends on the perspectives and contributions of all our employees. Diverse backgrounds and experiences make our business stronger.
If you are contacted for a job opportunity and require accommodation, please email people.culture@wittington.ca so we can ensure you have an accessible candidate experience throughout the recruitment process. All requests are confidential and used only to meet candidate needs.
We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted.
Number of Openings
1
Wittington recognizes Canada’s diversity as a source of national pride and strength. We have made it a priority to reflect our nation’s evolving diversity in the people we hire, and the culture we create in our organization. Accommodation is available upon request for applicants and colleagues with disabilities.
In addition, we believe that compliance with laws is about doing the right thing. Upholding the law is part of our Code of Conduct – it reinforces what our customers and stakeholders expect of us.
For more information, please visit and follow us on LinkedIn or Indeed
Please Note: If you have Employee Self Service (ESS) on Workday, apply to this job via the Workday application
Top Benefits
About the role
Location:
22 St. Clair Avenue East, Toronto, Ontario, M4T 2S7
About Us
Wittington Investments, Limited, a private Canadian company, is the holding company of the Weston group of companies, which includes George Weston Limited, Loblaw Companies Limited and Choice Properties REIT.
George Weston Limited is a Canadian public company, founded in 1882. George Weston has two operating segments: Loblaw Companies Limited, Canada’s largest food and drug retailer and a provider of financial services, and Choice Properties Real Estate Investment Trust, Canada’s largest and preeminent diversified REIT. With over 200,000 employees working at George Weston and its operating segments, the group of companies represent one of Canada’s largest private sector employers.
Job Description
About Us:
Wittington is a purpose-driven holding company that stewards the Weston family’s investments and philanthropic legacy. As the controlling shareholder of George Weston Limited - and through it, Loblaw and Choice Properties - we manage a global portfolio and support transformative initiatives across Canada. Wittington is also the home to charitable foundations that include the Weston Family Foundation and The Hilary and Galen Weston Foundation, which help advance Wittington’s philanthropic ambitions.
Our corporate values are the foundation of everything we do — guiding our decisions, shaping our culture, and defining how we succeed together.
- Integrity - We lead with integrity and humility
- Professionalism - We invest and serve with courage and excellence
- Long-term thinking - We prioritize long-term thinking and outcomes over short-term fixes and outputs
- Contributing - We believe that our greatest strength lies in our people, our culture and our shared purpose
The Opportunity:
As Senior Director, Investment Operations, you will be a senior leader responsible for the operational infrastructure, reporting accuracy, valuation processes, and treasury management that support Wittington’s diversified investment portfolio and the venture fund. This role blends strategic oversight with hands-on execution, ensuring that operations run seamlessly, valuations are rigorous and defensible, reporting is timely and insightful, and treasury functions maximize liquidity and capital efficiency. The role reports to the VP Finance and Treasury, who will mentor you to grow with the Company, challenge you to take on increasing levels of responsibility, innovate continuously, and develop your leadership abilities.
Key Job Responsibilities:
- Investment Operations
- Oversee trade execution, capital calls/distributions, settlement, and reconciliation across a multi-asset-class portfolio.
- Ensure portfolio data integrity, investment accounting accuracy, and timely close processes in coordination with finance teams and external administrators.
- Implement and maintain robust operational controls and governance frameworks.
- Ensure compliance with investment policies and procedures, including documentation, benchmarking, and custodian coordination.
- Investment Reporting
- Lead preparation of recurring and ad hoc investment performance reports, portfolio analytics, and exposure summaries for leadership, boards, and other stakeholders.
- Oversee the maintenance and improvement of investment systems (e.g., Northern Trust FOS) to enhance reporting flexibility and performance tracking.
- Ensure investment reports are created based on industry standards and completed and distributed with high quality and within the expected timelines.
- Build and enhance dashboards and reporting tools that deliver clear, actionable insights.
- Collaborate with investment teams to provide both qualitative and quantitative portfolio analysis for strategic decisions.
- Develop an ongoing working relationship with Investment and Finance colleagues to understand strategies, policies, and transactions as they pertain to performance measurement and other reporting.
- Valuation
- Oversee and manage the valuation process for all investments, including private equity, private funds, real estate, credit, and other assets.
- Develop and maintain valuation policies and procedures in compliance with accounting standards and industry best practices.
- Coordinate with investment teams, finance, auditors, and third-party valuation specialists to ensure accurate and timely valuations.
- Present and defend valuations to internal and external stakeholders as required.
- Treasury Management
- Direct daily treasury operations, including cash flow forecasting, liquidity management, payment processing, and banking relationships.
- Implement financing strategies and manage financial risks (e.g. FX, interest rate exposure).
- Ensure compliance with treasury-related regulatory requirements and internal controls, including segregation of duties and credit risk protocols.
- Lead automation and dashboard development to streamline treasury reporting and insights.
- Strategic & Leadership Contributions
- Support strategic decisions through financial insights on capital budgeting, investment strategies, and risk management.
- Partner with leadership to align operations, valuation, reporting, and treasury strategy with overall business objectives.
- Drive continuous improvement through technology adoption and process enhancements across investment and treasury functions.
- Stay abreast of industry standards and best practices while continuously seeking opportunities to enhance operational efficiency and mitigate operational risks
- Foster a culture of accountability, innovation, and professional development.
- Other ad-hoc duties as required.
Qualifications & Experience:
- Bachelor’s degree in Finance, Accounting, Economics, or related field required; MBA, CFA, or CPA strongly preferred.
- 10+ years of progressive leadership in investment operations, investment reporting and valuation within a private investment company, asset management firm, family office, or institutional investment environment.
- Deep knowledge of investment structures, fund administration, custody, and performance measurement.
- In-depth technical expertise in valuation methodologies for private and illiquid assets, including DCF, market comparables, and third-party appraisal processes.
- Proven ability to deliver accurate, board-ready investment reporting and defend valuations.
- Advanced treasury skills, including liquidity optimization, capital planning, and FX risk management.
- Proficiency with portfolio management systems, BI/reporting tools, and advanced Excel/data modeling.
- Strong governance and control mindset with experience building and enforcing operational and valuation policies.
- Exceptional communication, stakeholder management, and presentation skills.
- Ability to operate in a fast-paced environment with numerous competing priorities and reporting deadlines.
- Exceptional interpersonal skills with a proven ability to build trusting relationships at all levels of the organization.
- Strong team player with excellent problem-solving, communication, and client service skills, as well as the ability to take ownership and manage projects.
What We Offer:
- A friendly, collaborative, and inclusive culture
- A total rewards package that includes competitive compensation, flexible benefits as well as pension and investment plans
- Tuition reimbursement and training to help you reach your full potential
- Wellness programs and initiatives
Wittington is an equal opportunity employer committed to promoting a diverse and inclusive workplace. We know our success depends on the perspectives and contributions of all our employees. Diverse backgrounds and experiences make our business stronger.
If you are contacted for a job opportunity and require accommodation, please email people.culture@wittington.ca so we can ensure you have an accessible candidate experience throughout the recruitment process. All requests are confidential and used only to meet candidate needs.
We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted.
Number of Openings
1
Wittington recognizes Canada’s diversity as a source of national pride and strength. We have made it a priority to reflect our nation’s evolving diversity in the people we hire, and the culture we create in our organization. Accommodation is available upon request for applicants and colleagues with disabilities.
In addition, we believe that compliance with laws is about doing the right thing. Upholding the law is part of our Code of Conduct – it reinforces what our customers and stakeholders expect of us.
For more information, please visit and follow us on LinkedIn or Indeed
Please Note: If you have Employee Self Service (ESS) on Workday, apply to this job via the Workday application