Job Board
Outward Bound Canada

Head of Engagement and Development

Posted On: June 28, 2022
Closing On: July 21, 2022

Location: Preference for GTHA; Hybrid work environment is well-established
Effective: August 2022
Employment Type: fulltime
Level: beginner
Salary Range: $110,000 to $125,000 annually

Head of Engagement and Development

Outward Bound Canada is committed to inclusion and strives to have broad representation that reflects the diversity of Canada. We encourage applications from candidates who identify as Black, Indigenous, People of Colour or People of the Global Majority, members of the 2SLGBTQIA+ community, and all other equity-deserving groups


As a key member of the Outward Bound Canada leadership team, the Head of Engagement & Development is responsible for collaborating with other leaders to drive a positive growth mindset within the organization. All members of the leadership team are responsible for their own objectives, with the understanding that each member also supports their colleagues in achieving their objectives. This is a team effort. The success of the organization will largely depend on a highly collaborative and supportive leadership team.

The Head of Engagement and Development supports a team of philanthropy and advocacy professionals to build resilient funding streams. You will be the face of Outward Bound’s fundraising. The leader delivers a key role in supporting outreach, and donor relations, in collaboration with your colleagues in Marketing Communications, Operations, and Program.


Location: Preference for GTHA; Hybrid work environment is well-established

Term: Full Time

Salary: Commensurate with experience

Benefits: Comprehensive benefits package and Employee Assistance Plan

Reports To: Andrew Young, Executive Director

Application Deadline: July 21, 2022

Anticipated Start Date: August 2022


  • Grow your experience to the next level by providing both strategic and tactical direction.


  • Develop and manage a diverse philanthropy program including foundation, corporate and major gifts programs. Create a clear vision and strategy for a robust fundraising program.
  • Build a solid prospect management, research, and donor stewardship program to support retention, revenue generation, and fundraising (e.g.: identification, cultivation, and solicitation) of major gifts from individuals, corporations, and foundations.
  • Top line accountability for philanthropy-related revenue and expenses.
  • Participate in the shaping and management of the organizational budget, and inform financial modeling and decision-making.
  • Make major gift calls to donors independently and with staff and Board members.
  • Lead and direct Outward Bound’s Major Gift and other fundraising campaigns (i.e., Giving Tuesday, end-of-year), providing clear direction to team members about responsibility and goals.
  • Develop and maintain exceptional relationships with donors, potential donors, volunteers, staff, senior management team, and Board.


  • Support an environment in which staff are developed and empowered to deliver excellence and reach their full potential through the focused application of their talents and creativity, and through cross-functional collaboration.
  • Lead, manage and mentor a philanthropy team to continue to improve the philanthropy impacts both externally and internally through collaboration, diplomatic solutions, and partnership development
  • Engage Board members and other volunteers to extend and expand philanthropic reach.
  • Raise the level of engagement of Board members overall, coaching and motivating them, and providing them with the necessary information and tools to achieve fundraising objectives.


  • Own the revenue line for Philanthropy including responsibility for developing, managing, and monitoring the department’s annual budget.
  • Develop, refine and implement policies, procedures, and reports to ensure appropriate donor stewardship and retention.
  • Oversee the effective use and function of the donor / CRM database (NetSuite).
  • Work with the finance team to track financial and program performance.
  • Prepare plans and reports for the Executive Director and the Board of Directors where appropriate.


OBC recognizes relevant skills and knowledge can be gained through volunteer and life experiences as well as professional and educational backgrounds. Please outline in a brief cover letter why your passions and leadership growth align with OBC’s vision.

  • You are looking to advance your career in development and are excited to build a growing team and philanthropy program over the next 3-5 years
  • You thrive on building relationships, systems, and processes and successfully clarify ambiguous situations
  • A visionary, inspirational leader, with a great understanding of social systems of power and commitment to changing dominant narratives.
  • University degree or equivalent combination of work experience and education.
  • Minimum 10 years of successful and progressive philanthropic experience and/or fund development experience.
  • Demonstrated track record managing/growing diverse revenue streams, ideally with a focus on major gifts.
  • Digitally savvy and a strong communicator
  • Superior interpersonal skills, including the ability to relate effectively with people at all levels both internal and external.
  • Exceptional writing and presentation skills and the ability to effectively communicate to a diverse constituency.
  • Strong management skills, with the ability to mentor, coach, and supervise philanthropy and marketing professionals.
  • Ability to develop and manage budgets.
  • Demonstrated ability to identify, develop and close gifts.
  • Experience working with a non-profit Board of Directors.
  • Resilient, flexible, creative, and extremely adept at achieving tangible results while working in a dynamic, highly pressured, and often remote environment with minimum supervision.



Apply for this position by submitting your cover letter and resume as one PDF using this form.

Learn more about this role and check out our other current job openings here.