Posted On: 2020-01-09
Closing On: 2020-02-01
Location: Toronto, Ontario
Effective: As soon as possible
Employment Type: Full-Time
Level: Senior

Job Description

Position:                                  Director of Philanthropic Giving (Full Time)

Immediate Supervisor:           Head of Marketing & Philanthropy

Location:                                 Toronto, ON

Start date:                               February 2020

Since 1969, Outward Bound Canada (OBC) has inspired thousands of people to discover their true potential and contribute to a better, bolder, more compassionate and resilient society. A registered charity, OBC provides challenging adventures in the outdoors that develop self-respect, awareness of others, interpersonal skills, and a sense of accomplishment. With many Canadian youth struggling to thrive in an unpredictable and changing world, OBC is committed to helping them change the trajectory of their lives. OBC also offers a select number of programs for adults, including courses that support women who have experienced violence and/or abuse and veterans facing post-deployment.   


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 of Philanthropic 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 of Philanthropic Giving 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.


  • 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;
  • 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.


  • University degree or relevant post-secondary education;
  • 5-7 years experience in fundraising with a proven track record of success in Major Gifts;
  • CFRE Certification 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;
  • Evening and weekend work will be required from time to time.


Cover letters, resumes and trip logs can be submitted via our application database:

Click Here To Apply

Please identify the position as “Director of Philanthropic Giving” when you apply.

Application deadline: January 31, 2020

Outward Bound Canada is an equal opportunity employer. We thank all applicants for their interest; however, only candidates selected for an interview will be contacted.