Outside Looking In is (OLI) 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. OLI delivers innovative programs that inspire self-confidence, foster resilience, and create pathways for personal and academic success. While we are a little charity, we do big work! Grounded in education we deliver high-school accredited programs in remote & isolated Indigenous communities, that catalyze 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 into our programming to empower youth. High School completion is our mission, and the arts are how we get there. 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.

The Sr. Director will lead cross-functional teams of managers and frontline staff to ensure the effective implementation of OLI’s mission and strategic priorities. Reporting to the CEO and providing oversight for operations, the Director will collaborate with OLI’s Financial Controller and accounting team to coordinate the organization's finances and support the CEO with the annual budget and audit process.

 

Additionally, the 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 andhuman resources, fostering integration and alignment across all organizational functions.

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

 

Operations is the critical part of this role.

The Director will act as a “drone-level” leader, overseeing operations to ensure flawless execution, leading the collaboration and integration of external partners and internal program staff. This role provides leadership and operational direction for the development, implementation, andcontinuous improvement of all OLI programs to align with the organization's strategic goals. Operational leadership ensures seamless program delivery, with a focus on strengthening processes, systems and resource allocation. It will also lead the transition to new tools to optimize operations i.e. expense & travel management systems, logistics tools for multi-province program delivery, appropriate insurance coverage and coordinating with external legal counsel on various matters. This role is also responsible for the procurement of goods and services and ensures operational readiness ahead of critical organizational events, such as the Annual Dance Camp and flagship OLI Showcase.

Collaborating with the finance team (outsourced). Ensure prudent financial reporting practices including payables, receivables from funding partners and the flow of payments in to and out of the organization. Review and approve expenditures for and lead financial policy development and refinement for financial integrity, supporting strategic growth. This role is responsible for the production of accurate, timely and transparent financial reporting for all audiences.

· Evaluate, select and maintain OLI’s technology infrastructure to support a growing organization, which includes the integration and optimization of platforms such as Humi, QuickBooks, and Notion to enhance team efficiency and operational oversight. Identify opportunities for technology improvements and ensure system security, cost-effectiveness, and compliance.

·   Play a pivotal role in supporting the operational execution of OLI’s annual Indigenous youth Camp and Showcase, a flagship event critical to the organization’s mission and donor engagement. This entails oversight of logistical planning, resource allocation, and vendor management while ensuring fiscal responsibility to deliver a quality show that audiences, Indigenous communities and donors have come to enjoy and expect. 

·  Manage the overall HR function and refine OLI’s performance management, compensation, and manages employee benefit programs and relationship with providers to support a high-performing and engaged team. The Director ensures compliance with employment legislation, and leads key HR initiatives, including the integrity of payroll and employment contracts. 

· Manage organizational governance activities, including preparing for Board (and its committees) meetings, maintains and reports on necessary governance documentation adhering to best practices. Monitor legislative & regulatory changes to enhance risk management frameworks and ensure policies are current and compliant.

·  Be the organizational leader. Collaborate with the CEO and Associate Directors to develop and implement organizational strategies that enable growth, including development of evaluative frameworks that demonstrate the organization’s operational performance and impact.  To accomplish this, the role leads andcoaches direct reports, including associate directors, building their capacity and foster a culture of accountability and continuous improvement.

·  Support revenue generation by ensuring donor reporting requirements are met, including preparing and analyzing financial components of funding applications, budgets, and program spending reports. This includes managing goods donated in kind. The Director leads efforts to manage organizational assets, including in-kind inventory management. Develop and execute strategies for asset liquidation or reallocation when necessary.

●   Minimum of 7-10 years of progressive management experience, including 5 years in a senior leadership role, preferably in the non-profit or charitable sector. A Bachelor’s degree in Business Administration, or a related field;a CPA designation or master’s degree with financial oversight experience in the annual audit process areconsidered assets.

●  Familiarity with Indigenous communities, cultures, and reconciliation initiatives is considered a strong asset.

●   Demonstrated experience in operations management, including contract negotiations, vendor management, and process optimization.

●   Is tech savvy and can critically assess and manage IT systems and platforms with the ability to identify and implement technology solutions to enhance efficiency.

●  Experience in human resources leadership, including payroll management, performance management systems, compensation reviews, and employment legislation compliance.

●  Track record of managing organizational governance, including preparing for Board and Committee meetings, risk management, and policy development.

●   Ability to analyze operational challenges, provide defensible recommendations for improvement and sustainability. Has a demonstrated financial acumen, can apply principles of cash flow management, budgeting, forecasting, financial reporting, and variance analysis. Ideally, has a strong understanding of non-profit sector requirements, the Canada Not-for-Profit Act, and donor reporting requirements.

●   Experience overseeing large, complex events including operational logistics, resource allocation, vendor coordination, and budget management.

●   Strong leadership and team management skills, with the ability to coach, mentor, and develop staff at all levels of the organization.A

 Exceptional communication skills, with the ability to distill complex financial and operational information into clear, actionable insights.

●   High emotional intelligence to lead the organization, with the ability to build trust and cultivate a positive culture. Demonstrated ability to manage multiple functions, solve problems efficiently, and drive results under tight timelines. 

Understanding of regulatory compliance and familiarity with legal filings related to charitable organizations.

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