Senior Director, Operations and Finance

OLI Careers; Toronto; Hybrid; CAD 90,000 - 120,000; Full time

Job summary

A charitable organization in Toronto is seeking a Senior Director to lead operations and finance. This role requires strong leadership skills, management experience in the non-profit sector, and the ability to oversee financial processes. The ideal candidate will have a Bachelor's degree in Business Administration and familiarity with Indigenous communities. This is a full-time position that offers a hybrid work model.

Benefits

Health Insurance

Dental Insurance

Life Insurance

Qualifications

• 7-10+ years of progressive management experience, including 5+ years in senior leadership, preferably in non-profit or charitable sectors.
• Familiarity with Indigenous communities and reconciliation initiatives is a strong asset.
• Proven ability in organizational governance, risk management, and financial principles.

Responsibilities

• Lead teams to ensure effective operations, reporting to the CEO.
• Oversee operations to ensure flawless execution.
• Collaborate on financial reporting and manage payables and receivables.

Skills

Employee Relations

Management

Conflict Management

Operations Management

Leadership

Education

Bachelor’s degree in Business Administration

CPA designation

Tools

Humi

QuickBooks

Notion

Job description

About Us

Outside Looking In (OLI) is a registered charity based in Toronto, operating across Canada for 18 years. Serving Indigenous youth exclusively, OLI is dedicated to empowering youth through the transformative power of dance education and leadership development. We deliver innovative programs that inspire self-confidence, foster resilience, and create pathways for personal and academic success. Though a small charity, we do big work! Grounded in education, we deliver high-school accredited programs in remote and isolated Indigenous communities, catalyzing youth to complete high school. As an Indigenous-led organization, for over 18 years, we have focused our programming on cultural inclusivity and community involvement by integrating Indigenous cultural values and traditions. High school completion is our mission, and the arts are our pathway. The culmination of OLI's dance programs is our annual high-profile showcase, where youth perform on prestigious stages across Canada, such as Toronto's Meridian Hall. This experience builds confidence and inspires participants to dream big.

About The Sr. Director:

• The Senior Director will lead teams of managers and frontline staff to ensure effective operations, reporting to the CEO. They will collaborate with OLI’s Financial Controller and accounting team to coordinate finances and support the CEO with the annual budget and audit processes.

Additionally, the Senior Director will play a key role in organizational governance, enterprise risk management, strategy, and policy development. This role encompasses leadership of OLI’s technology infrastructure, procurement, and human resources, fostering integration and alignment across all organizational functions.

They must have strong financial acumen to support budget development, oversee staff and vendor expenses, and organizational expenditures. The Senior Director should have a proven ability to lead compliance activities and manage complex operations. Excellent organizational and communication skills, coupled with a collaborative mindset, will ensure success in this role.

Core Responsibilities of the Sr. Director of Operations & Finance:

Operations: The Director will oversee operations to ensure flawless execution, leading collaboration with external partners and internal program staff. They will provide leadership for the development, implementation, and continuous improvement of all OLI programs to align with strategic goals. Operational leadership includes strengthening processes, systems, and resource allocation, leading transitions to new tools, managing logistics, insurance, legal matters, procurement, and ensuring operational readiness for major events like the Annual Dance Camp and Showcase.

Financial Oversight: Collaborating with the finance team, ensure prudent financial reporting, manage payables and receivables, review expenditures, and develop financial policies supporting strategic growth. They will produce accurate, timely, and transparent financial reports for diverse audiences.

Evaluate and maintain OLI’s technology infrastructure, including platforms like Humi, QuickBooks, and Notion, to enhance efficiency and security. Identify opportunities for technology improvements and ensure compliance.

Support the operational execution of key events such as the Indigenous Youth Camp and Showcase, overseeing logistics, resource allocation, vendor management, and fiscal responsibility to ensure high-quality delivery that meets organizational standards and expectations.

Human Resources: Manage HR functions, refine performance management, oversee compensation and benefits, ensure legal compliance, and lead HR initiatives including payroll and employment contracts.

Leadership: Manage governance activities, prepare for Board meetings, monitor regulatory changes, and ensure policy compliance. Collaborate with the CEO and Directors to develop and implement growth strategies, build staff capacity, foster a culture of accountability, and support revenue generation through donor reporting and asset management.

Candidate Requirements:

• 7-10+ years of progressive management experience, including 5+ years in senior leadership, preferably in non-profit or charitable sectors.
• Bachelor’s degree in Business Administration or related field; CPA designation or master’s degree with financial oversight experience is an asset.
• Familiarity with Indigenous communities and reconciliation initiatives is a strong asset.
• Experience in operations management, contract negotiations, vendor management, process optimization, and IT systems management.
• Leadership experience in HR, including payroll, performance management, and employment law compliance.
• Proven ability in organizational governance, risk management, financial principles, and managing large events.
• Strong leadership, communication, emotional intelligence, and problem-solving skills.
• Understanding of regulatory compliance and legal filings for charities.

Key Details:

• Type: Full-time, with a three-month probation period.
• Benefits: Health, Dental, Life Insurance (post-probation).
• Reports to: CEO.
• Start Date: Negotiable, ASAP preferred.
• Location: Hybrid. Must have stable internet, private workspace, and ability to attend in-office one day/week. Valid driver’s license required.

We encourage all First Nations, Métis, Inuit, and Indigenous peoples of North America to self-identify in their applications.

Required Experience: Executive level.

Key Skills:

Employee Relations, Employee Evaluation, Management, Profit & Loss, Conflict Management, Operations Management, Project Management, Budgeting, Leadership, Supervising, Financial Planning.

Employment Type: Full-Time

Experience: 7-10+ years

Vacancy: 1