Senior Manager Investment Operations

Winchesters; Toronto; On-site; CAD 125,000 - 150,000; Full time

Benefits offered by this job

Excellent benefits

Job summary

Winchesters is seeking a Senior Manager of Investment Operations in Toronto to build and lead a dedicated ops function from the ground up. You will own trade support, reconciliation, valuation oversight, and portfolio reporting across assets, with a hands-on approach in a small team.

The role requires 7+ years in investment operations, strong process design skills, and excellent communication with investment teams and external partners. CPA/CFA is a plus; English fluency essential.

Qualifications

• 7+ years of experience in investment operations, middle office, or fund administration.
• Experience building or significantly improving an operations function from the ground up.
• Strong understanding of trade lifecycle, reconciliation, and valuation processes.
• Excellent communication skills with investment teams, external partners, and senior leadership.

Responsibilities

• Design and implement investment operations processes, controls, and systems for a function being built from the ground up.
• Oversee trade support, settlement, and position reconciliation across custodians, fund administrators, and external managers.
• Own valuation oversight and NAV validation for private and illiquid holdings.
• Lead investment performance reporting and analysis for timely, accurate leadership visibility.
• Act as primary operational liaison to custodians, fund administrators, external investment managers, and auditors.
• Partner with the investment team and Treasury on cash movements while excluding banking from the team.
• Maintain data integrity across portfolio and accounting systems and evaluate new tools as the function matures.
• Hire, onboard, and develop the investment operations team as it grows.

Skills

Investment operations

Trade reconciliation

Valuation oversight

Portfolio reporting

Team leadership

Stakeholder communication

Education

Accounting/Finance/Business degree

Job description

$125,000-$150,000 compensation with excellent benefits

Our client is a private investment company managing a diversified portfolio across a range of sectors and asset classes. As the organization grows, they are building a dedicated investment operations function for the first time and are seeking a Senior Manager of Investment Operations to lead it from the ground up.

This is a hands-on, builder-focused role for someone who's comfortable creating processes, controls, and infrastructure where none currently exist. You'll own investment operations end-to-end — trade support, reconciliation, valuation oversight, and reporting — across all sectors and asset classes, with treasury and cash management sitting outside the scope of this team. Over time, you'll build out a small team including an Investment Operations Associate and a reporting-focused hire, though the near-term work will be highly hands-on.

Responsibilities

• Design and implement investment operations processes, controls, and systems for a function being built from the ground up.
• Oversee trade support, settlement, and position reconciliation across custodians, fund administrators, and external managers, spanning all sectors and asset classes, both public and private.
• Own valuation oversight and NAV validation, with particular attention to private and illiquid holdings.
• Lead investment performance reporting and analysis, ensuring leadership has timely, accurate visibility into portfolio activity.
• Act as the primary operational liaison to custodians, fund administrators, external investment managers, and auditors.
• Partner closely with the investment team and Treasury to ensure clean handoffs on cash movements and funding activity, while keeping banking and liquidity management outside this team's scope.
• Maintain data integrity across portfolio and accounting systems, and help evaluate and implement new tools as the function matures.
• Hire, onboard, and develop the investment operations team as it's built out, starting with an Investment Operations Associate and a reporting-focused role.

Requirements

• University degree in Accounting, Finance, Business Administration, or a related field. CPA, CFA, or CA designation an asset.
• 7+ years of experience in investment operations, middle office, or fund administration, ideally spanning multiple asset classes (public equities, fixed income, private equity, real estate, etc.).
• Experience building or significantly improving an operations function, process, or control environment from the ground up.
• Comfortable working in a small, hands-on environment without an existing team or established playbook.
• Strong understanding of the trade lifecycle, reconciliation, and valuation processes across both liquid and illiquid investments.
• Excellent communication skills, with the ability to work closely with investment teams, external partners, and senior leadership.