Controller

Controller – Multi-Entity Sports & Education Group 

Organizations: Athlete Institute, Orangeville Prep Academy (Not-for-Profit), Pretty River Sport & Entertainment, Opportunities & Pathways Foundation, Rusty Rock Inc. 

Position Summary 

The Controller is a senior finance leader responsible for overseeing all accounting, financial reporting, internal controls, and compliance activities across a multi-entity group consisting of a high-performance sports institute, a not-for-profit academy, and a sport entertainment business. 

This role manages a team of two finance staff and works closely with cross-functional leaders including CEO, CFO, President, Facility Director, and Program Director to support strategic decision-making, operational excellence, and long-term sustainability. The Controller will ensure accurate financial reporting, strong governance, and scalable financial systems suitable for a growing, mission-driven organization. 

Key Responsibilities 

Financial Leadership & Oversight 

• Lead all accounting operations for multiple legal entities, ensuring accurate and timely month-end, quarter-end, and year-end closes 
• Prepare and review consolidated and entity-level financial statements 
• Ensure consistency in accounting policies and procedures across all entities 
• Maintain and enhance internal controls, risk management, and financial governance frameworks 

Not-for-Profit & Compliance Management 

• Oversee not-for-profit accounting, including fund accounting, restricted funds, and donor/grant reporting 
• Ensure compliance with CRA regulations, not-for-profit standards, and applicable financial reporting frameworks 
• Prepare required filings, including T3010s and HST returns 
• Track event management and sponsorship activities 

Budgeting and Cashflow Management 

• Lead annual budgeting and rolling forecast processes across all entities 
• Partner with operational team to align budgets with program, facility & growth plans 
• Provide variance analysis, financial insights, and recommendations to leadership 
• Develop dashboards and reporting tools to support data-driven decision-making 
• Manage cash flow forecasting, working capital, and liquidity planning 
• Monitor revenue streams including tuition, programs, events, sponsorships, rentals, and grants 

People Management & Team Development 

• Manage, mentor, and develop a team of two finance staff 
• Set clear priorities, performance expectations, and professional development plans 
• Foster a collaborative, accountable, and service-oriented finance function 

Cross-Functional Collaboration 

• Work closely with the President to support initiatives and long-term planning 
• Partner with the Facility Manager on maintenance budgets, Capital planning and cost controls 
• Collaborate with the Program Director to ensure financial sustainability of programs and events 
• Provide financial guidance to non-financial leaders in a clear, practical manner 
• Systems & Process Improvement 
• Implement best practices for efficiency, automation, and financial transparency 

Qualifications & Experience 

• CPA designation (CPA, CA / CPA, CMA / CPA, CGA) is an asset 
• 5+ years of progressive accounting and finance experience 
• Prior experience managing multiple legal entities 
• Experience with not-for-profit accounting and compliance is an asset 
• Proven people management experience 

Skills & Competencies 

• Strategic thinker with strong analytical and problem-solving skills 
• Hands-on leader comfortable operating in a dynamic, entrepreneurial environment 
• Excellent communication skills with the ability to translate financial information for non-finance stakeholders 
• High attention to detail with the ability to manage multiple priorities 
• Strong ethics, integrity, and commitment to organizational mission 

Why Join This Organization 

• Opportunity to lead finance across a unique, mission-driven sports and education ecosystem 
• High visibility role with direct influence on strategy and growth 
• Collaborative leadership team and impactful work environment