National Indigenous youth program Outside Looking In partners with Sun Life to build pathways to careers in tech

Small Business Canada

For many Indigenous young people living in remote communities across Canada, geographic isolation can present a barrier to career planning resources, mentorship, education, and opportunities. Outside Looking In (OLI)a national Indigenous youth charity is helping to change that through a partnership with Sun Life centered on increasing exposure among Indigenous youth to digital literacy and in-demand career avenues in technology.

Students from nine Indigenous communities participate in Sun Life Discovery Day in partnership with Outside Looking In (CNW Group/Outside Looking In)
Students from nine Indigenous communities participate in Sun Life Discovery Day in partnership with Outside Looking In (CNW Group/Outside Looking In)

Sun Life Discovery Week, an immersive technology career education summit, which took place from February 13 – 15, 2024, saw youth from nine Indigenous communities converge on Toronto for three jam-packed days of seminars, hands-on learning, post-secondary discovery, and mentorship from industry leaders. Made possible by Sun Life, the summit featured programming at Sun Life, Microsoft, and Toronto Metropolitan University, and covered topics ranging from artificial intelligence to information technology, cyber security, cloud computing, entrepreneurship and digital technology start-ups, career pathways, human resources, financial technology, and more.

Sun Life invited Microsoft to be part of the Discovery Week experience, and expand the Alumni’s exposure to a wide variety of technology careers. For OLI Alumnus Kai Wood, a seminar with Gillian Vaughn, an Indigenous Software Engineer at Microsoft, was a pivotal moment, helping to shift his perspective and cement his desire to build a career that merges art with technology. As a student at Assiniboine Community College for creative digital arts, he now hopes to bring Indigenous storytelling to the forefront through video game design. 

“I don’t often see people like myself represented in spaces and it can feel like Indigenous people aren’t welcome. It often makes me want to give up,” said Wood. “Hearing from an Indigenous person at Microsoft who is succeeding in a career I aspire to helps me understand a new perspective, and it gives me the courage to carry on. My Discovery Week experience was important because it has shown me that everyone can be included and have a place.”

“Providing access to resources, mentorship and learning opportunities is an important way to drive equity and inclusion. We work hard at Sun Life to create a sense of belonging and Sun Life Discovery Week is an extension of that,” said Laura Money, Executive Vice-President, Chief Information and Technology Innovation Officer, Sun Life. “We’re thrilled to partner with Outside Looking In to help us continue creating a diverse pipeline of talent and ensure the best, diverse perspectives are shaping how we deliver Client impact.”

Sun Life Discovery Week is part of the Tech for Life stream of OLI’s Alumni Career Development Program. In its third year, the OLI Alumni Program is designed to meet the needs of Indigenous youth ages 18-26 as they transition from high school toward their future careers, with a focus on leadership, professional and career development, strengthening personal and life skills, and employability.

“Sun Life employees have been integral to our Alumni program success, generously donating their time to provide guest lectures on career and technology industry trends,” said Hope Sanderson, CEO at OLI. “We’re thrilled with our partnership for Sun Life Discovery Week. Together we can help break down barriers by building access to valuable information, skills and connections, to drive greater opportunity for Indigenous youth, especially for young people living in areas where these types of resources and opportunities generally do not exist.”  

Through the Alumni program, youth take part in weekly seminars and attend guest lectures on topics ranging from digital and financial literacy, program management, human resources, law, health and wellness, and more. The program also offers mentorship with leading professionals and field trips to urban centres, post-secondary institutions, and businesses to learn about establishing personal financial objectives, academic admissions processes, and career avenues.

Participants of the OLI Alumni Program are graduates of OLI’s flagship dance program, OLI Dance, a high school-accredited dance program that empowers Indigenous youth in grades seven to 12 to do well in school, graduate high school, become community leaders and discover their full potential.

OLI Alumni taking part in Sun Life Discovery Week come from nine communities across Canada:

  • Gakijiwanong Anishinaabe Nation, ON
  • Garden Hill First Nation, MB
  • Iqaluit, NU
  • Membertou First Nation, NS
  • Native Canadian Centre of Toronto, ON
  • Pikangikum First Nation, ON
  • Pinaymootang First Nation, MB
  • St. Theresa Point First Nation, MB
  • Wasagamack First Nation, MB

Many of OLI’s Alumni will return to Toronto, along with more than a hundred OLI Dance program participants, for Canada’s largest Indigenous youth performance – OLI’s 17th Annual Showcase, taking place at Meridian Hall this May. Additional information about the 2024 Showcase will be announced in the coming weeks.

Since the inception of its dance program in 2007, OLI has played a critical role in empowering thousands of Indigenous youth from over 30 communities and achieving high school graduation rates of over 96 per cent while improving academic standing, health and wellbeing. Over 80 per cent of youth participants report improved mental health and self-esteem; 90 per cent report an increased level of importance on education, and 86 per cent report better grades.

About Outside Looking In

Founded in 2007, Outside Looking In is a nationally registered charitable organization that aims to empower Indigenous youth through the transformative art of dance, while they pursue education, increase their mental and physical health, and engage in self-expression. For information, visit

About Sun Life

Sun Life is a leading international financial services organization providing asset management, wealth, insurance and health solutions to individual and institutional Clients. Sun Life has operations in a number of markets worldwide, including Canada, the United States, the United Kingdom, Ireland, Hong Kong, the Philippines, Japan, Indonesia, India, China, Australia, Singapore, Vietnam, Malaysia and Bermuda. As of December 31, 2023, Sun Life had total assets under management of $1.40 trillion. For more information, please visit

Sun Life Financial Inc. trades on the Toronto (TSX), New York (NYSE) and Philippine (PSE) stock exchanges under the ticker symbol SLF.

Media Contacts:

Rise PR on behalf of OLI
Andrea McLoughlin

Adrienne Kakoullis
[email protected]

For Sun Life
Kelsey Rutherford
[email protected]

SOURCE Outside Looking In

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