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Current Opportunities

Director of Philanthropy | Calgary Academy

The Organization

Headwater Learning Foundation (HLF) is a non-profit entity that connects a network of educators with partners and communities committed to improving and transforming education. By providing financial means and assistance, HLF provides security and sustainability to organizations pushing the boundaries of educational change. The Foundation is part of the Headwater Learning Group, which also consists of Calgary Academy and Headwater Learning Solutions.

The Headwater Learning Group began with Calgary Academy Society. Through the partnership with related organizations, Headwater Learning Foundation and Headwater Learning Solutions, the organizations are broadening their collective impact to foster and support the advancement of education.

Calgary Academy was founded in 1981 and is a private school renowned for empowering unique learners to unleash their potential while pursuing lives of passion and purpose. Since its earliest days as pioneers in inclusive education, Calgary Academy has lived and breathed by a simple yet profound ethos: place the individual needs of each student at the heart of everything they do. Rooted in this commitment, the spirit of Calgary Academy is embodied by a unique and authentic energy. The organizationā€™s growth-oriented, nurturing and inclusive culture promises that each student will be empowered to exceed their own expectations and to believe in the boundless opportunities the future holds. Hope, belonging, and a palpable sense of optimism fill the school and hearts of all employees. Calgary Academyā€™s four pillars and guiding principles are woven throughout innovative programming proven to be incredibly successful since its inception; however, the true essence of Calgary Academy can only be captured by a feeling that is difficult to portray with words but undeniable in spirit. It is a feeling that fosters safety and life-long loyalty, and it is why Calgary Academy is a place so many families, students, staff, and alumni are so proud to call home.

Vision: To be a beacon of possibility for richly personalized, engaging learning experiences that empower learners to pursue lives of passion and purpose.

Mission: We design engaging, dynamic, student-centered experiences that nurture a caring, inclusive culture and instill a love of learning.

For further information about Calgary Academy, please visit:

For further information about Headwater Learning Solutions, please visit:

The Opportunity

Job Title: Director of Philanthropy

Reports to: Direct line to the Executive Director of Finance & Corporate Services and indirect line to the President & CEO

Direct reports: 2

Location: Calgary, AB


Reporting directly to the Executive Director of Finance and Corporate Services and indirectly to the President and Chief Executive Officer, the Director of Philanthropy will work in partnership to assist in the further development and full implementation of the fund development plan for Headwater Learning Foundation, Calgary Academy and Headwater Learning Solutions. This individual will oversee the organizationsā€™ fundraising efforts in the areas of major gifts and planned giving. The fund development team exists for the mutual benefit of all three organizations and their stakeholders. The successful candidate will demonstrate strong leadership in establishing and developing long-term philanthropic relationships with high-capacity prospects and donors while leading a team of fundraisers. The Director of Philanthropy will work independently and collaboratively with all departments in building out operational successions. This individual is a self-starter who will balance their time between contributing to fundraising strategy, identification, cultivation, solicitation and stewardship of a portfolio of prospects and donors and coaching a high performing team. The Director of Philanthropy will develop and implement strategies that promote long-term sustainable growth and deepen the organizationsā€™ relationships with donors.

Key Accountabilities


  • Lead the development and implementation of the Capital Campaign developing high level metrics surrounding the success of the Campaign
  • Successfully deliver on specific revenue targets related to the Capital Campaign
  • Develop strategies to solicit and secure major gifts, including prospect research, customized proposal writing, presentations and direct involvement in major gift solicitations
  • Communicate the organizationsā€™ objectives in a persuasive and inspiring manner with all stakeholders
  • Build and increase support for the organizations through active participation in identifying, cultivating and stewarding relationships and connections

Strategic Development:

  • Lead the continued development, implementation and expansion of the fund development program
  • Contribute to sustaining a culture of philanthropy through sharing the impact of philanthropy on ability to advance mission and vision, and supports new program development and initiatives
  • Support the organizationā€™s 4-year strategic plan


  • Counsel and guide the organizationsā€™ methods for fundraising and the role of philanthropy
  • Establish performance metrics, drive the team to results and regularly report progress to the leadership team and Board of Governors/Directors
  • Build out team capacity through investing time into coaching and mentorship
  • Successfully manage fundraising budget

First Year Deliverables / Measures of Success

Success in the first year will be determined by the candidateā€™s ability to:

  • Successfully demonstrate the capability to ā€˜hit the ground running,ā€™ as it relates to the Capital Campaign
  • Firmly establish themselves as a trusted advisor within the organizations
  • Support the achievement of defined goals for direct reports including metrics to evaluate success
  • Develop new and enhance existing relationships with donors and key stakeholders
  • Develop and actualize a fund development strategy
  • Actively participate in securing major gifts

Candidate Profile


  • Bachelorā€™s Degree
  • CFRE certification is considered an asset


  • Minimum ten yearsā€™ of progressively responsible fundraising experience and a proven record of successful cultivation and solicitation of major gifts (five and six figure gifts)
  • Minimum five yearsā€™ experience leading a team
  • Demonstrated working knowledge of planning and execution of capital campaigns
  • Solid knowledge of ethical principles and best practices relating to fundraising, prospect research, donor relations and communications
  • Previous experience and familiarity with Raiserā€™s Edge
  • Strong understanding of budgeting processes and data management

Competencies and Attributes

  • Conveys a high degree of comfort in identifying, contacting, and developing new major gift prospects
  • Possesses superior interpersonal skills, demonstrating diplomacy and foresight
  • Demonstrates an outgoing, positive, group-win approach and a willingness to learn, teach and share
  • Exemplifies excellent verbal and written communication skills
  • Successfully manages multiple competing priorities in a fast-paced environment
  • Demonstrates professional maturity, resourcefulness, and self-discipline in engaging in the pursuit of the organizations
  • Displays an ability to focus on the big picture without losing sight of the details in cooperation with the fund development team
  • Develops and maintains cooperative, successful working relationships with staff, donors and volunteers through exceptional influencing, tact, and diplomacy skills
  • Thinks strategically and creatively about engaging donors, developing plans of action, and following through
  • Demonstrates presence, self-confidence, sound judgment, and superior problem-solving ability


The Headwater Learning Group is committed to equity, diversity and inclusion and recognizes that a diverse team benefits and enriches our work and is essential to operational excellence. We welcome applications from all qualified individuals and encourage women, members of racialized communities, Indigenous persons, persons with disabilities, and persons of any sexual orientation or gender identity to confidentially self-identify at time of application. In accordance with provincial legislation, accommodation will be provided throughout the recruitment, selection and/or assessment process, upon request, to applicants with disabilities. All qualified candidates are encouraged to apply.

How to Apply:

Please send your resume in Word or PDF format to: Copy and Paste the following job title and code and place it in the subject line of your email so we can identify the job and confirm receipt of your application:
A020987 (ANOH-027674) Director of Philanthropy | Calgary Academy - AB - Calgary and Area (OTIAPPLY)

Please note that only those candidates meeting the selection criteria, established by our client, will be contacted further. Although we may not contact you directly for this particular role, all applications will be reviewed as we would like to consider you for future opportunities that may be appropriate. We encourage you to continue to visit our website at as our opportunities are updated on a regular basis.