Regional Director, Community Investments

Purpose

In collaboration with a team of Regional Directors, lead the efficient and effective delivery of the OTF Investment Strategy. Oversee and lead outreach, counselling, assessment and monitoring activities delivered by Program Managers within an assigned geographic area ensuring excellence in grant- making and customer service. At the same time lead teams of volunteers who bring knowledge of local needs to the assessment and decision -making stages of the process. As a member of the Leadership Forum, champion and help to deliver the strategic direction of the foundation through inter-departmental collaboration to plan and deliver on the OTF business plan.

Key Areas of Responsibility

Program Management

• Work collaboratively within the department and across the organization to provide input to and oversee delivery of the Ontario Trillium Foundation Investment Strategy

• Lead Program Managers to deliver accountability and provide excellent customer service

• Oversee volunteer understanding and implementation of the Investment Strategy and OTF policies, processes and standards

• Oversee funding recommendation processes within assigned areas - providing leadership in analysis and resolution of issues and ensuring on-going compliance with policies and standards

• Provide leadership in the analysis and resolution of sometimes contentious and, or complex issues

• Work collaboratively and within assigned areas to oversee and support effective and efficient program delivery (confirming compliance with policies, processes and standards, and ensuring responsive outreach and counselling, accurate and timely assessments, and helpful and accountable monitoring)

• Problem solve and apply good judgement to decision-making

• Feed information as required to corporate reports including quarterly progress on KPIs

• Provide input to the OTF Risk Registry and Framework and implement mitigations to ensure accountable and accessible granting practices and value for money in the use of public funds

Strategic Leadership

• Champion the strategic direction of the Foundation internally and externally

• Provide strategic advice to the Vice President, Granting, on grant issues, and resource management

• Work collaboratively and provide input as required to department and organization al strategies for achieving business plan goals

• Oversee staff and volunteer understanding of OTF priorities, business needs, policies, processes and procedures

• Effectively manage change on an on-going basis

• Provide input on and oversee sustainable measures to mitigate identified risks

• Work collaboratively to develop and implement strategies for achieving departmental and business plan goals (operational and organizational)

• Oversee a local operational budget within the context of a larger department budget

• Oversee training and learning opportunities for staff and volunteers to understand sector and community needs as related to the OTF Investment Strategy

• Collaborate with OTF leaders to successfully deliver the business plan

Performance Management

• Lead, coach, and mentor a high performing team to deliver on OTF’s Investment Strategy and Business plans as applied to Community Investment department priorities and responsibilities

• Support Program Managers located in various parts of the province to provide efficient, effective and excellent customer service

• Provide ongoing guidance, feedback, recognition and coaching to staff

• Drive excellence amongst staff by ensuring robust support, encouraging development opportunities and by helping staff to see the link between their function(s) and the OTF mandate and business plan

• Provide inclusive leadership in employee recruitment, retention and professional development.

• Conduct semi-annual performance reviews with direct reports, and address performance

• problems as they occur

• Support professional development, learning and maintenance of a strong team including succession planning for the future

• Support exceptional delivery of granting through the OTF Investment Strategy

• Identify and manage resources needed to achieve objectives in assigned team areas

Financial Management

• Lead target setting/decision-making of grant allocation targets for assigned area

• Work collaboratively to set and oversee operational budgets for assigned area and within department budget

• Problem solve and apply good judgement to decision-making pertaining to applicant/grantee financial statements, financial health and/or financial capacity

Skills and Attributes

• Supervisory, leadership and collaborative skills

• Ability to lead a team, be part of a team and maintain a positive attitude

• Ability to think independently

• Conceptual, analytical and problem-solving skills

• Ability to use good judgment and exercise good decision-making

• Ability to motivate self and others generating a high level of performance

• Strong understanding of OTF’s Investment Strategy and granting policies

• Excellent interpersonal, communication and presentation skills

• Experience with Change Management

• Resilience and ability to work under the pressure of multiple deadlines and cyclical demands

• Familiarity with Financial Statements

• Experience working in a digital setting - a high degree of comfort with technology and various platforms

• Willingness and ability to travel in Ontario (once encouraged under public health guidelines)

• Granting experience an asset

• Distance management skills an asset

• Bilingualism (French & English) required

Leadership Competencies

• Inclusive Leadership

• Accountability, Excellence & Agility

• Create a Vision for the Future

• Nurture Growth

• Collaborate

• Lead Change

• Be Decisive

Experience and Education

• Post-secondary degree in a relevant discipline.

• Five to seven years’ progressive and relevant experience or an acceptable equivalent in education and experience.

• Experience working within a high-performance culture

• Experience building and leading teams in a dynamic environment

• Experience with decision-making and managing change

• Project management experience

• Knowledge of/ experience with the diversity of OTF’s clientele and stakeholder groups

How we support diversity, inclusion and accessibility

We are building an inclusive workforce that reflects the communities we serve. We encourage everyone interested in working with us to apply, including people with disabilities, Indigenous, Black and racialized individuals, as well as people from all ethnicities, cultures, sexual orientations, gender identities and gender expressions.

Learn more about the work the Ontario Trillium Foundation is doing to create an inclusive, anti-racist, accessible and diverse workplace:

• Diversity, equity and inclusion initiatives
• Accessibility
• Anti-discrimination Policy 

OTF is committed to accommodating applicants with disabilities throughout the hiring process, in accordance with the Accessibility for Ontarians with Disabilities Act (AODA). This job posting falls under the Public Service of Ontario Act, 2006.

The use of AI is not used to screen, assess, or select applicants.

While we thank all applicants for their interest, only those selected for an interview will be contacted.

Application Deadline: January 23, 2026