Chief Program Officer

3 days ago

Toronto, Canada Outside Looking In Full time

**Introduction**

The Chief Program Officer (CPO) will provide strategic leadership for OLI programmatic and community impact activities, lead the development and expansion of a collaborative approach between OLI and community partners, and lead OLI’s longstanding charitable and community capacity-building programs. The CPO will have the exciting opportunity to help take one of Canada’s most innovative and vibrant philanthropic organizations to its next level of impact. The CPO reports to the President and CEO, serves on OLI’s leadership team, and will grow the program team as necessary over the next 3 years of OLI’s Strategic Plan. In addition to staff, the position will interact with committee members, board members, donors, and external partners.

**About OLI**

Outside Looking In (OLI) is a national registered charity that has been providing programming for Indigenous youth since 2007. Through experiential education that explores self-expression, embracing challenges, and shaping the journey to success, Outside Looking In supports and empowers Indigenous youth from high school to their career path of choice.

**Position Description**

The Chief Program Officer (CPO) will provide strategic leadership for OLI programmatic and community impact activities, develop and expand a collaborative approach between OLI and community partners, and lead OLI’s longstanding charitable and community capacity-building programs. The CPO will have the exciting opportunity to help take one of Canada’s most innovative and vibrant philanthropic organizations to its next level of impact. The CPO reports to the President and CEO, serves on OLI’s leadership team, and will grow the program team as necessary over the next 3 years of OLI’s Strategic Plan. In addition to staff, the position will interact with committee members, board members, donors, and external partners.

The CPO works to advance OLI’s mission and to:

- Serve as OLI Canada’s lead charitable consultant and direct its capacity-building and convening programs
- Build and lead a program department of 5 current FTE, and hire additional employees as necessary
- Facilitate engagement of OLI’s Investor Partners in strengthening OLI Canada and our Charitable Partners
- Work with the CEO on the execution of all strategic goals and initiatives.

**PROGRAM DEVELOPMENT**
- Be the key leader and representative for OLI, which includes the planning and implementation of a shared system of referrals, social capital efforts, data collection and evaluation and requires interacting with families, direct line staff, program supervisors, CEOs, OLI donors and volunteers, and the evaluation teams.
- Lead inclusive, collaborative, and efficient internal processes around the operationalization and implementation of OLI’s core and inter-connected programs, which include:

- OLI Dance
- OLI Future Leaders
- OLI Entrepreneurship
- OLI Indigenous Rising Stars
- OLI Alumni Accelerator

**TEAM MANAGEMENT & LEADERSHIP**
- Hire, manage, coach, and mentor a growing team of program associates, inspiring them through a period of change as we develop and transition to new programmatic frameworks and approaches.
- Lead, inspire, and facilitate OLI’s Community Partners in their volunteer engagement with OLI programs, including management of a portfolio of community partner-powered working groups.
- Develop and promote inclusive processes for feedback, alignment, and development of support for OLI’s charitable and community partners.
- Support OLI ‘s (volunteer) Lead Partners in managing the charitable teams by providing strong project management skills, and thought leadership, and facilitating positive team dynamics.

**COMMUNITY RELATIONSHIPS**
- Internally and externally model our transition from a “knowing organization” to a “learning organization,” focused on asking the right questions and lifting up the expertise of our charitable partners.
- Serve as the lead representative for OLI’s programs and impact, including as a speaker and convener.
- Maintain active and broad external engagement to ensure awareness of local community needs and opportunities, as well as a broad understanding of trends and needs in the regional and national OLI, charitable and philanthropic ecosystems
- Build and maintain relationships with relevant peers in local philanthropy, government, the charitable sector, and the business community that may lead to collaborations and partnerships to leverage our resources and increase our impact.
- Serve as a guide and coach to OLI Partners to help them deepen their knowledge of charitable and philanthropy and enhance their charitable capacity-building skills.

**Qualifications**

All OLI employees have the following responsibilities:

- Represent OLI’s principles, values, culture, and community investment philosophy
- Build strong relationships based on trust, mutual respect, humility, equity, and partnership
- Actively inspire, engage, and

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