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Position: Director, Leadership Giving (Full Time)
Organization: Outward Bound Canada
Location: Toronto, ON (Open to Remote)

Immediate Supervisor: Head of Marketing & Philanthropy
Start date: Immediately

Outward Bound Canada is committed to helping Canadian youth change the trajectory of their lives. With young people desiring to thrive in an unpredictable and changing world, OBC, a registered charity, offers social-emotional education through experiential adventures in the outdoors. Since 1969, OBC has inspired over 150,000 participants, with a particular emphasis on providing greater access to those facing socioeconomic barriers, to discover their potential. These experiences develop resilience, social and emotional intelligence, and environmental leadership to contribute to a better, more compassionate, and resilient society. The impact of our work on young people in Canada is found in our recent case for support.


Outward Bound Canada is seeking an experienced fundraising professional with a strong track record of securing and managing five- and six-figure donations. The Director, Leadership Giving will be responsible for leading the cultivation, solicitation, and stewardship of OBC’s major gift portfolio (donations of $15,000+). Reporting to the Head of Marketing and Philanthropy, the Director will oversee a portfolio of 75-125 donors and prospects while working collaboratively with other members of the Philanthropy Team and the Fundraising Cabinet. The Director will identify opportunities to welcome new donors to OBC, while also strengthening existing relationships, leading to greater engagement with OBC’s mission, increased giving levels and multi-year pledges. In addition, the Director, Leadership Giving will provide leadership of OBC’s legacy giving campaign and supervision of those tasked with managing annual and special events.


  • Develop and maintain an in-depth knowledge of OBC programs and funding priorities.
  • Provide strategic oversight of the major gift portfolio (donations of $15,000+), building relationships with individuals and organizations capable of this level of support.
  • Establish an effective stewardship program for various levels of major gifts, which includes appropriate reporting and engagement activities.
  • Establish goals to move donors up the giving cycle and solicit multi-year pledges.
  • Work collaboratively with the rest of the Philanthropy Team to ensure successful execution of fundraising and stewardship strategies, programs and to maximize revenue.
  • Maintain a challenging but realistic portfolio of major gift prospects to cultivate, solicit and steward, both personally and in tandem with senior staff and volunteers.
  • Develop the organization’s legacy giving program and promote with key stakeholders.
  • Support the Executive Director (ED), Head of Marketing & Philanthropy, Board members, Fundraising Cabinet and volunteer committees in coordinating and implementing national fundraising efforts.
  • Provide leadership in the design and execution of annual and special events including third party events and community opportunities that raise funds in support of Outward Bound Canada and increase engagement.
  • Ensure systems are in place to provide acknowledgement, recognition, reporting, and effective communication for donors and prospects.
  • Organize, manage and track fundraising activities and information, ensuring donor activity is maintained in Salesforce.
  • Utilize prospect research tools to identify and qualify potential major gift donors as well as the cultivation and solicitation of prospects to meet revenue targets.
  • Assist in the creation of donor communications and fundraising materials in collaboration with the Philanthropy and Marketing teams.
  • Represent OBC at fundraising events and on fundraising projects as required.
  • Provide relevant and engaging reporting programs for the major donor program.
  • Other duties as assigned.


  • Minimum of 5-7 years major gifts and/or gift planning experience for a registered charity.
  • Certificate in Fundraising Management or Fundraising Executive designation (CFRE) an asset.
  • Experience working with senior volunteers and advancement staff.
  • Must have excellent prospecting skills and proven ability to uncover leads from databases and other sources.
  • Proven track record in major gift cultivation and solicitation activities.
  • Demonstrated awareness of the donor relationship cycle (identification, cultivation, solicitation, stewardship); principles of moves management and solid understanding of how major gift activities relate and connect to other major gift areas within development such as events, stewardship, research, annual and planned giving.
  • Flexible and adaptable; able to work both independently and as part of a team; proven ability to set priorities; work with minimal supervision and meet deadlines.
  • Proficiency with Salesforce, MS Office including Word, Excel and Outlook, and high degree of comfort with a donor database for tracking prospect activity.
  • Excellent interpersonal skills and a positive attitude to work effectively and collaboratively with a variety of stakeholders such as volunteers, donors, and alumni.
  • Superior organizational, administrative, analytical, verbal and written communication skills.
  • Exceptional attention to detail, ability to develop and execute complex plans and manage multiple priorities and deadlines.
  • Professional presence, sound judgment, diplomacy and tact. Ability to maintain confidentiality and work with sensitive information.
  • Position requires a police background check, including a Vulnerable Sector Check.
  • Evening and weekend work will be required from time to time.


Cover letters and resumes can be submitted via our application database: Click Here To Apply

Please identify the position as “Director, Leadership Giving” when you apply & please indicate you saw this posting at GoodWork.

Salary Range: $80,000-$100,000/year and a comprehensive benefits package.

Application deadline: August 13, 2021 (applications will be reviewed on a rolling basis)

Outward Bound Canada is an equal opportunity employer, we recognize that people come with a wealth of experience beyond the technical requirements of a job, if your experience is close to what you see listed, please consider applying. Outward Bound Canada strives to have a broad representation that is reflective of the diversity of Canada and values the diversity of people and communities and is committed to inclusion in our organization. We encourage applications from all individuals who will help us achieve our goals, including women, racialized people, members of the 2SLGBTQIA+ community, and all other equity-deserving groups.

We thank all applicants for their interest; however, only candidates selected for an interview will be contacted. Please let us know if you require accommodations at any stage during the hiring process.


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Note: This posting is provided on an "As Is" basis and for general informational purposes only. People and Planet (also known as "GoodWork") is not responsible for the content, accuracy, timeliness, completeness, legality, reliability, quality or suitability of this posting. We do not screen or endorse the organizations or individuals involved. If you decide to accept an offer of employment, volunteering or any other arrangement, you do so at your own risk and it is your responsibility to take all protective measures to guard against injury, abuse, non-payment or any other loss. Please read our full Terms & Conditions.

Current status: Open/apply now.   Date posted: Jul 16 2021    ID: 60662