Senior Director, Operations and Finance

ABOUT OUTSIDE LOOKING IN This is an exciting opportunity for someone to assume a key senior role on the leadership team of our charity, which serves Indigenous youth in Canada. Outside Looking In, while we may be a small organization, we do big work! Outside Looking In is an Indigenous-led education organization serving Indigenous youth across Canada for 18 years. We are Canada’s largest Indigenous youth charity, and we present Canada’s largest live youth performance every year in Toronto at the Meridian Hall to an audience of thousands. This role works closely with the CEO and will help to lead us in delivering on our mandate. JOB SUMMARY: The Senior Director of Operations oversees all operational, administrative, and financial functions. This role directs and manages the operations related to the successful delivery of OLI’s core programs. This is a senior role, leading teams of managers and frontline staff who deliver programs and engage with community partners while other members of the leadership team focus on day-to-day programming responsibilities. The scope of this role includes all supporting functions such as finance, operations management, human resources, technology, and performance management. DETAILED ROLE DESCRIPTION: Organizational Leadership Collaborate with the CEO and Leadership Team on strategic planning initiatives. Implement strategic and annual business plans, ensuring integration across all organizational functions, including programs, communications, human resources, development, and finance. Partner closely with the development team to align programs with funding opportunities and support program leaders in fundraising efforts. Develop, maintain, and oversee systems and processes that ensure efficient management of daily program staff activities and support the organization's overall goals. Lead the ongoing IT infrastructure development to meet the growing organization's needs, including hardware and software solutions. Work with the CEO to ensure effective Board management, including planning for (agendas, board motions, minutes, etc.), and participate actively in regular Board meetings. Play a key role in managing overall compliance and enterprise risk management. Support CEO in the development and refinement of the strategic plan, including the creation of all strategic planning processes and documents, and prepares for presentation to various audiences. Take a leadership role in the development of organizational policies, monitor for changes to best practices, and make recommendations to the CEO and board. Manage all governance documentation and ensure they are updated and current as necessary (bylaws, regulatory filings, etc.). Financial Leadership: Develop the annual budget, ensure goals are met, review financial performance, and enhance program budgeting and reporting practices, including cash flow management, variance reporting, and budget forecasting. Oversee and provide direct guidance to bookkeeper and other finance roles. Coordinate all audit activities, ensuring timely and accurate completion. Review and approve the preparation and finalization of quarterly and annual financial reports and key metrics for the Board. Provide timely financial reports to the CEO, offering insights into the organization’s economic health, including cash flow, expenditures, and budgetary progress. Regularly monitor financial trends, identify potential risks, and recommend strategic actions to ensure financial stability. Report to the Board on financial matters, ensuring clarity around the organization's financial position, key metrics, and budget adherence. Develop recommendations to the CEO for long-term financial sustainability. Program, Team, and Staff Management: Lead and manage all staff and activities to effectively meet organizational goals, ensure integration across all areas and measure programmatic impact towards achieving the OLI mission. Identify opportunities for organizational and programmatic growth. Develop and maintain metrics consistent with relevant plans and create a system of ongoing evaluation, ensuring robust work plans and alignment between the individual, team, and organizational goals and priorities. Supervise, coach, and collaborate with senior program staff to ensure programmatic and team success. Plan and organize internal staff meetings, including preparing agendas and troubleshooting internal management issues. Envision, plan, and execute events to increase staff integration, support organizational goals, and build team orientation. Manage and refine the organizational performance management process and systems, including overall compensation and benefits programs (liaises and negotiates with external vendors and manages associated HRIS platforms related to human resource functions). Administration Oversee day-to-day operations of the overall organizational administration. Manage office leases, vendor relationships, and contracts, ensuring compliance with organizational policies. Coordinate and maintain an inventory of office supplies, equipment, and services to support staff. Support staff in navigating office logistics and liaise with property management and external vendors for maintenance and office-related concerns. Technology and IT Management Oversee the management of all hardware, software, and technology services, ensuring system security, functionality, and efficiency. Manage relationships with external IT vendors and service providers, ensuring cost-effective and quality service delivery. Stay abreast of emerging and best-in-class technologies that enable and enhance organizational operations (i.e., use of AI tools). Ensure data security and compliance with legal and organizational standards, including implementing cybersecurity measures. Plan for and manage technology infrastructure improvements, upgrades, and maintenance. Provide IT support and training to staff, ensuring they have the necessary tools and resources for their work. REQUIREMENTS: Bachelor's degree in Business Administration, Management, Finance, or a related field. A Master’s degree or relevant professional certifications would be an asset. At least 7-10 years of management experience, with at least 3 of these in a senior management role and in a non-profit or similar organizational environment. Proven experience in strategic planning, financial management, and operational oversight, preferably in a growing organization. Experience in managing budgets, cash flow, and financial reporting, including working with auditors and overseeing financial compliance. Proven track record in governance, risk management, compliance, and enterprise compliance, particularly in non-profit or charitable sectors. Experience working in a multi-disciplinary team environment with a focus on collaboration and inclusion. Understanding of regulatory compliance and familiarity with legal filings related to charitable organizations. Key Details: Type: Full-time with a three-month probation period. Benefits: Health and Dental, Life Insurance (after probationary period). Reports to: CEO. Start Date: ASAP. Location: Hybrid. All applicants must have access to a stable internet connection and a private working space. All applicants must be able to attend in-office days at our Toronto office. We encourage all First Nations, Metis and Inuit peoples or Indigenous peoples of North America to self-identify in their applications. #J-18808-Ljbffr