Job Posting


“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.”

The Organization—Outside Looking In
Established in 2007, Outside Looking In (OLI) is a national charity and Indigenous-led organization that supports and empowers Indigenous youth in their career path of choice. Offering opportunities to be actively engaged in the arts, OLI provides Indigenous youth with an outlet to be creative and to find a safe space where they can perform, learn, connect, be heard, and feel connected within their community. In turn, this encourages Indigenous youth to stay in school and complete their education.

As the organization faces unprecedented demand, OLI provides a full cycle of programs across Canada that assist and support youth from the Intermediate grades, through high school, post-secondary education and career preparation. OLI offers accredited Dance, Leadership, Work-Study, and Entrepreneurship programming to communities, organizations, Friendship Centres and Public-School Boards across Canada.
Along with academic support, OLI programs add value and key support for schools through:
• Providing structure and routine
• Creating a safe space for social interaction
• Promoting the importance of well-being and physical health
• Elevating aspirations and life goals
• Fostering a sense of belonging
• Instilling an appreciation for music and dance

All OLI programs are infused with the values and teachings of long-term commitment, accountability, responsibility, and perseverance. OLI’s approach to experiential learning—combining classroom time with regular dance rehearsals and instruction from a professional choreographer—offers participants a unique channel to showcase their talents and accomplishments. Overall, OLI graduates are living proof that an arts education can lead to greater confidence and a self-determined future.
In addition, and on the path to Reconciliation, OLI offers Canadians with a safe place to learn about Indigenous Peoples, beyond what they see and read in the media. Recent story-telling initiatives have revived an Indigenous tradition while inviting non-Indigenous audiences to connect with the realities of OLI participants. In turn, OLI youth are able to learn more about what is happening outside of their communities and to get a glimpse of potential opportunities. Each spring, OLI’s Annual Showcase is held at Meridian Hall in downtown Toronto, the largest soft-seat theatre in Canada. The Annual Showcase, which is Canada's largest Indigenous youth performance, features youth from current participating communities and highlights the successes of program participants throughout the year. Audiences are invited to learn about the youth participating in the show as well as join in the celebration of their accomplishments.
OLI’s Strategic Plan was recently refreshed, and its focus revolves around five interconnected goals, including:

• To achieve sustainable, operational excellence, that keeps pace with the organization’s growth
• To create a fundraising mission that resonates with all Canadians and reaches a broad and diverse audience through various marketing channels
• To offer rich and relevant programs to Indigenous youth that enhance life skills and empower self-confidence
• To entertain and educate through OLI's Annual Showcase, which transforms the lives of Indigenous youth and our audiences
• To expand OLI's presence nationally as a top-tier non-profit organization and grow its reputation for good governance and unwavering results
For more information about OLI, please visit

The Role—Chief Executive Officer

As the founding Chief Executive Officer (CEO) of OLI steps down from the organization’s most senior leadership position, the Board is seeking potential candidates to fill the role. Candidates must have a passion for empowering Indigenous communities, appreciate and understand the transformative power of the arts (especially dance), maintain an energetic approach toward stakeholder and community relations while understanding the importance and relationship between Indigenous values and education.

Reporting to the Board of Directors, the CEO is responsible for all OLI activities and operations and provides leadership and support to advance the OLI vision and priorities. Collaborating with the board, the CEO develops OLI’s strategy and creates operational plans to fulfill the organization’s mandate. The CEO is responsible for overseeing OLI’s staff and programs and for maintaining an inclusive and respectful organizational culture. Building on the OLI brand and growing its presence across the country, the CEO will devise an action plan to expand OLI’s programs and increase the positive impacts for Indigenous youth. The CEO will continue to build on existing strategic relationships while actively seeking new partnerships across all stakeholder groups.

The CEO is also responsible for the following:
Leadership & Management:
• Oversee administrative functions including finance, fundraising, communications, reporting and systems
o Recommend timelines and resources needed to achieve organizational goals
o Ensure effective systems are in place to track and report progress and results
o Regularly communicate results to the board, donors, and other key stakeholders
• Lead, coach, develop and retain OLI’s high-performance leadership team
• Actively engage and energize OLI’s volunteers, board members, donors, partners and funders
• Develop and maintain a strong working relationship with the Board of Directors; Seek and build board involvement to guide the strategic direction and impacts of OLI programs nationally
• Ensure ongoing, high-quality programs are offered by OLI and a high standard of excellence is consistently achieved
• Ensure rigorous, consistent program evaluation
• Introduce new program ideas that support the organizations mission, vision and values
Fundraising & Communications:
• Act as OLI’s main spokesperson and lead all media, community, government, partner and donor relations
• Expand revenue-generating and fundraising activities to support existing program operations and expand OLI programs and presence across Canada, in alignment with board’s strategic vision
• Build the OLI brand; Deepen and refine all aspects of communications, from digital strategies to more traditional external relations
• Generate new opportunities through existing and new relationships and partnerships
Planning & Growth:
• Support the expansion of OLI program offerings for Indigenous communities across Canada
o Continue to build new partnerships and relationships in new locations
o Create connections with political and community leaders to expand OLI’s network and presence across a diverse range of communities
• Inspire regional and national replication of the OLI model by utilizing multiple communication channels and emphasizing youth successes, stories and results

Candidate Requirements and Attributes:
• Advanced degree, ideally an MBA, with at least 12 years of senior management experience
• Lived experience with Indigenous cultures and ways of being and knowing; An ability to lead in a culturally safe and respectful way with diverse Indigenous participants, communities and organizations
• Direct experience effectively leading and scaling a regional and/or national performance- and outcomes-based organization; Ability develop and operationalize strategies to grow an organization
• Experience working directly in the non-profit field
• Strong marketing, public relations, fundraising and relationship management skills; Proven ability to develop, operationalize strategies and grow an organization
• Unwavering commitment to quality programs and data-driven program evaluation; Strong project management skills
• Strong administration and management experience; Ability to coach and manage staff, develop high-performance teams, set and achieve strategic objectives, and manage a budget
• Experience and familiarity with youth programming
• Past success working with and reporting to a Board of Directors with the ability to cultivate existing board member relationships
• Exceptional written and verbal communication skills; A persuasive and passionate communicator with excellent interpersonal skills
• Knowledge of an Indigenous language would be an asset
• A values-based and action-oriented individual who leads with a combination of the following qualities: entrepreneurial, adaptable, innovative, passion, integrity, positivity, mission-driven and self-directed
• Location: GTA - OLI head office is on the Six Nations of the Grand River Territory with an administration office in downtown Toronto
• Travel: The role requires frequent travel to remote communities within Canada; Applicants must have a valid driver’s license and be able to travel by air

Location: The OLI headquarters is located within Six Nations of the Grand River territory and the administrative office is located in downtown Toronto. It would be appropriate for the successful candidate to reside within the Greater Toronto Area (GTA)
The City of Toronto
The name Toronto is derived from the Mohawk word “tkaronto,” which means “where there are trees standing in the water.” It is the traditional territory of many nations, including the Mississaugas of the Credit, the Anishnabeg, the Chippewa, the Haudenosaunee, and the Wendat peoples. It is now home to many diverse First Nations, Inuit and Métis peoples, along with other Indigenous groups that represent this valued community.

Toronto has a population of 2.8 million people, making it the largest city in Canada, the fourth-largest city in North America, one of the top 25 cities globally for its quality of living, and the best place to live in Canada, according to MoneySense.

Toronto welcomes 40 million tourists a year. It supports a lively art and culture scene that includes museums, galleries, performing art organizations, and many festivals (including the Indigenous Art Festival). Toronto is recognized as one of the most diverse and multicultural cities in the world.

The Greater Toronto Area
The GTA is divided into four regional municipalities: Durham, Halton, Peel and York. Together with Toronto, it has a population of approximately 6.5 million people. The GTA is vast. It extends along Lake Ontario to the east and west, and north of the Toronto city centre.
Some notable neighbourhoods in the GTA include Brampton; Burlington; Markham; Mississauga; Oakville; and Richmond Hill.

To Apply
Please note that preference will be given to Indigenous applicants.

Please submit a cover letter and resume to Your cover letter should include a description of your personal connection to Indigenous peoples and communities; and, how you have successfully led programs and/or services that are respectful and inclusive of traditional knowledge and cultural teachings.

Application Deadline: 
Wednesday, February 1, 2023
Type of Work: 
Full Time
Education Level: 
University (Graduate)
Additional Languages: 
Knowledge of an Indigenous language would be an asset
Prefered Method(s) of Application: 
By E-Mail

Employer Details

Leaders International

Wenda Lee
1 Rideau Street
Ottawa, ON K1N8S7