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Current Opportunities

Director of Philanthropy – Calgary Academy


Headwater Learning Foundation 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 organization’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 Academy’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.

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

The 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:

Headwater Learning Solutions is a non-profit entity with the vision to be a catalyst for equity and innovation in learning. While the goal from the very beginning was to broaden Calgary Academy’s impact on education and shape the future of learning, HLS began to see a distinct trend in the unmet needs of learners, and the vision around equity and innovation in education solidified. Its greatest challenge is developing a system that ensures learners can gain and hone skills that will prepare them for everything life has to offer. By bringing bright minds together, we’re driving lasting change in schools, communities and the education system. Adapting the success of the Calgary Academy model to help other underserved learners has already made an impact in underfunded inner-city schools and on-reserve schools.

For too long, education systems have missed the students on the margins. Success for most learners is not enough. Headwater Learning Solutions exists to meet the needs of all learners.

For further information about Headwater Learning Solutions, please visit:



Job Title: Director of Philanthropy

Reports to: Direct line to the Executive Director of Finance and Corporate Services and indirect to the President and Chief Executive Officer

Direct Reports: 2

Location: Calgary, Alberta



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 organizations’ 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 organizations’ 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 organizations’ 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 and provide input into the organizations’ new, upcoming 4-year strategic plan


  • Counsel and guide the organizations’ 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


  • Opportunity to develop a culture of philanthropy in an organization that has a strong reputation and focused on making a difference in the lives of students and their families
  • To work in a small, closely knit campus environment, across all levels of the organization and to witness firsthand the success of your efforts
  • To be a leader in the organization working closely with the Executive Leadership Team, Board and CEO
  • Join an organization that believes in the principles of Respect, Enthusiasm, Altruism, Commitment and Honesty (REACH)
  • Opportunity to be a builder, leave a legacy and develop the strategy, readiness, and plans for future capital campaigns



Success in the first year will be determined by the candidate’s ability to:

  • Successfully demonstrate the capability to ‘hit the ground running,’ 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



The successful candidate will have the following:


  • Bachelor’s degree


  • Minimum ten years’ of progressively responsible fundraising experience and a proven record of successful cultivation and solicitation of major gifts (five and six figure gifts)
  • Minimum five years’ experience leading a team
  • Demonstrated working knowledge of planning and execution of capital campaigns
  • CFRE certification would be desired
  • Solid knowledge of ethical principles and best practices relating to fundraising, prospect research, donor relations and communications
  • Previous experience and familiarity with Raiser’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



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:
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.