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WP Osborne Executive Search Inc.

Controller

Toronto, ON, Canada
Greater Toronto Area, Canada, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Nov 28, 2026
Posting language: English
Posted: Oct 29, 2026

Original job description

Starlight Investments, in conjunction with WP Osborne Executive Search, is seeking a Controller to join its Portfolio Finance team.

Controller, Portfolio Finance

The Controller will lead the finance team to ensure the financial operations of a portfolio of entities, ensuring the delivery of accurate and timely financial reporting, analysis, budgeting, and forecasting. As a key member of the portfolio finance team, the Controller will serve as a strategic business partner to the Asset Management and Investments teams, providing insightful financial and operational information to support informed decision-making and optimize property performance and investor returns. As part of the company’s commitment to innovation, the successful candidate will embrace AI and emerging technologies to improve efficiency, enhance quality, and help the broader team adapt to the evolving finance profession.

Key Responsibilities:

Investor Reporting and Financial Reporting

Lead and oversee the portfolio’s accounting operations, ensuring the accuracy, completeness, and integrity of journal entries, balance sheet reconciliations, and monthly/quarterly/annual financial reporting.
Own the preparation, review, and delivery of operating results and consolidated, pooled, and statutory financial statements.

Financial Accounting & Analysis

Lead the monthly financial close and reporting process for the portfolio, ensuring the accuracy, completeness, and timeliness of financial data, variance analysis, and management reporting.
Oversee the integrity of portfolio financial systems and reporting outputs, acting as a data steward and partnering with cross-functional teams to identify and remediate data or process issues, while driving continuous improvement initiatives to enhance accounting processes and reporting efficiency.
Lead the annual audit process, coordinating with external auditors, preparing and reviewing audit working papers to ensure the timely completion of audited financial statements.
Support financial planning and analysis, including the review and preparation of budget inputs and outputs for properties and funds.

Treasury & Cash Management

Review property manager cash calls and weekly cash flow forecasts and liquidity reporting, identifying funding requirements and trends.
Oversee loan compliance and covenant reporting, ensuring timely and accurate reporting and proactively identifying potential covenant issues or forecasting risks.

Transaction support (Acquisitions, Dispositions, Financing, etc.)

Lead the financial and accounting aspects of property acquisitions, dispositions, financings, refinancings, and other complex transactions.
Partner with internal stakeholders on acquisitions, dispositions, financing activities, and other strategic initiatives by providing financial analysis, due diligence, and accounting guidance to support informed decision-making.

Coaching and Mentorship

Lead, mentor, and develop a team of Managers and Accounting professionals by providing coaching, performance feedback, technical guidance, and professional development opportunities while fostering a culture of accountability, collaboration, and continuous improvement.

AI and Technology Adoption

Act as an early adopter and role model for AI and automation as a core tool of how work gets done within the team.
Proactively apply approved AI tools to enhance the efficiency and quality of accounting, analysis and reporting workflows, and convert into repeatable processes.
Identify, test and help implement AI-enabled process improvements.
Apply strong professional judgment to review and validate AI-assisted output, safeguarding accuracy, data integrity and compliance.

Qualifications

The ideal candidate will have a university degree in Accounting, Finance, Business, or a related field, with a CPA, CFA, or MBA, and has 5+ years of progressive accounting/finance experience, including leading a team. The candidate brings strong knowledge of accounting principles, external audit experience, and advanced Excel and Microsoft Office skills, with ERP experience required; Yardi, Power BI, and Workiva are assets. Exceptional communication, leadership, organizational, and relationship-management skills are essential, along with the ability to manage competing priorities and deadlines. The successful candidate will demonstrate sound judgment, accountability, and a continuous-improvement mindset, with experience leveraging technology, automation, and AI to enhance finance processes and operational efficiency.

Application

Qualified candidates can submit their resume via LinkedIn.

The compensation structure is comprised of a base salary that is market competitive and based on factors such as experience, education, designations, and skillset. It also includes a discretionary annual performance bonus tied to weighted performance targets and company performance, and company medical/dental benefits, healthcare spending accounts, a tiered employer matching group retirement savings plan and parking/Presto allowance. Other benefits include maternity top-up, investment opportunities in the company’s funds, summer office hours, annual company-wide volunteer day and many more.

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More about this job

Responsibilities

Lead portfolio accounting and financial reporting, including monthly close, financial statements, audits, budgeting, forecasting, cash management, and loan covenant reporting. Support acquisitions, dispositions, and financing transactions while developing the finance team and adopting AI and automation to improve workflows.

Requirements

Requires a university degree in accounting, finance, business, or a related field, with a CPA, CFA, or MBA, and at least five years of progressive finance or accounting experience, including team leadership. Candidates should have strong accounting and audit knowledge, advanced Excel and Microsoft Office skills, ERP experience, and strong communication, organizational, relationship-management, and technology-adoption capabilities.

Skills

Financial Reporting
Accounting Operations
Financial Analysis
Budgeting and Forecasting
External Audit
Treasury and Cash Management
Cash Flow Forecasting
Loan Covenant Reporting
Transaction Support
Team Leadership
Coaching and Mentorship
Advanced Excel
ERP Systems
AI and Automation
Data Stewardship
Process Improvement

Benefits

Medical and Dental Benefits
Healthcare Spending Accounts
Parking or Presto Allowance
Maternity Top-Up
Investment Opportunities in Company Funds
Summer Office Hours
Annual Company-Wide Volunteer Day

Visa sponsorship

Not detected in the job text

Keywords

Portfolio Finance
Real Estate
Accounting
Financial Reporting
Consolidated Financial Statements
Statutory Financial Statements
Monthly Close
Variance Analysis
Budgeting
Forecasting
External Audit
Audit Working Papers
Treasury
Cash Management
Liquidity Reporting
Loan Compliance
Covenant Reporting
Acquisitions
Dispositions
Financing
CPA
CFA
MBA
Advanced Excel
Microsoft Office
ERP
Yardi
Power BI
Workiva
AI and Automation

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