Job Board
Outside Looking In

Director, Sponsorship and Development

Posted On: March 17, 2022
Closing On: April 18, 2022

Location: Hybrid / Remote
Effective: ASAP
Employment Type: fulltime
Level: intermediate
Salary Range: 80000-90000


Outside Looking In is seeking a Director, Sponsorships and Development, to join our newly created Development team. As the Director, Sponsorships and Development, you will be part of an inclusive organization that provides educational and support services for indigenous youth across Canada, from fly-in reserves to urban youth.
The ideal candidate has exceptional organizational, communication, and relationship management skills. As a primary contact for sponsors and donors, the Director, Sponsorships and Development, will play a key role in their cultivation and stewardship.


Outside Looking In (OLI) is a national registered charity 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.
OLI runs various programs throughout the year at locations across Canada. Some of our programs include a national high school accredited dance program, a leadership program, and a work-study program. For more information about OLI, please visit

Position Overview

  • Proactively identify, cultivate and solicit sponsorships to achieve fundraising goals.
  • Maintain and foster strong long-term relationships with all sponsors.
  • Develop sponsorship packages and submissions.
  • Ensure all contractual obligations are effectively tracked and delivered within set timelines.
  • Strengthen the overall structure for sponsorships management – including policies, procedures and database management.
Major Gift Donor Program 
  • In collaboration with the Marketing and Communications team, develop a major gift donor program – including benefits, stewardship, and retention.
  • Participate in each step of the donor pipeline including: research, identification, cultivation, briefing, request for support, follow up, stewardship, and recognition.
Grant Writing:
  • Research and identify proposals, grants, and other public/private funding opportunities within Canada for education, health and economic development.
  • Complete grant applications and proposals.
  • Meet proposal deadlines by establishing priorities and schedules for information gathering, writing, reviewing, and obtaining approvals.
  • Serve as the primary contact for granting entities.
Ambassador Program:
  • Develop a national volunteer-based “Ambassador Program” to assist in raising awareness of OLI’s mission and support fundraising initiatives – including goals, milestones and annual review of the Ambassador team.
  • Build strong long-term relationships and steward Ambassadors through regular discussions and meetings (virtual and in-person).
  • Research, develop and implement a platform to assist with national volunteer fundraising initiatives.
Annual Event Strategy
  • Develop and execute a strategic approach to OLI’s annual event with a focus on maximizing revenues all while delivering an outstanding experience for all attendees.

Key Details:

  • Type: Full-time with a three-month probation period.
  • Benefits: Health and Dental, Life Insurance (after probationary period).
  • Reports to: Vice President, Development and Communications.
  • Start Date: ASAP.
  • Location: Remote. All applicants must have access to a stable internet connection and a private working space.
  • Travel: Travel to remote communities within Canada as well as to Toronto for meetings.
We encourage all First Nations, Metis and Inuit peoples or Indigenous peoples of North America to self-identify in their applications.


  • Bachelor’s Degree in Public Relations, Marketing, Communication, or an equivalent combination of appropriate education and experience.
  • 6-8+ years of proven experience in planning, leading and managing fundraising and development projects – ideally in a non-profit setting.
  • Skilled in creating powerful and captivating written and oral communications for fundraising (including grant writing).
  • Ability to convey complex ideas through simple and concise materials.
  • Expert negotiator and relationship builder – with a proven record for cultivating strong and lasting relationships.
  • Flexible and able to multi-task; can work within a remote, fast-moving environment.
  • Experience using CRM systems to manage stakeholder relationships.
  • Experience in sales is considered an asset.
  • Comfortable using MS Office and GSuite.