Alamo Heights School Foundation
From Strategic Planning to a $10M Endowment Campaign
The Challenge:
Alamo Heights is one of the most affluent communities in San Antonio, which leads to the common assumption that its public schools must be well-funded. The reality tells a different story. Like districts across Texas, Alamo Heights ISD faces a widening gap between what the state provides and what a premier public education truly requires. The Alamo Heights School Foundation understood this gap but faced a harder challenge: how to mobilize a community to give generously when most residents assume their schools already have what they need? Our partner needed a clear, actionable roadmap, not a lengthy traditional strategic plan, to turn that understanding into action. And they needed messaging that could shift a deeply held misconception about school funding in an affluent community.
Our Approach:
Cielo began working with the Foundation in the summer of 2024, starting with a Board retreat designed to help leadership dream big and define what the Foundation needed to accomplish by 2030. From that session, we developed a Strategic Action Plan, a faster, higher-level alternative to a traditional strategic plan, built for a Board ready to move. To ground the plan in real community sentiment, we interviewed more than fifteen key stakeholders, including current and former Board members and donors across a range of demographics and giving levels. Those conversations shaped messaging that named the funding gap plainly and invited the community to help close it. That messaging was adopted first by the Foundation Board, then by district staff, and has since spread throughout the community. We also helped reimagine the Foundation’s annual appeal strategy, writing the copy and supporting the design of its appeal card and other external-facing materials. As the refreshed strategy and messaging took hold, one Strategic Action Plan priority, a new endowment campaign, moved sharply up the timeline. In the summer of 2025, the Foundation again called on Cielo, this time to lead an Endowment Campaign Feasibility Study ahead of a bold $10 million campaign to grow the Foundation’s endowment. We interviewed more than thirty-five donors, prospective donors, and friends of the Foundation, and delivered a comprehensive report with clear recommendations for moving forward. Following the Board’s unanimous vote to move forward in late fall 2025, Cielo has continued to serve as strategic counsel to the Board and Campaign Committee, developing the campaign’s full case for support and providing ongoing training to the Campaign Committee at its regular meetings.
From Our Partner:
“We had the privilege of working with Cielo Strategy Group, and the experience truly exceeded our expectations. We chose them because of their extensive expertise and deep understanding of our donor base, and they delivered on every level. From the beginning, they took the time to listen to our unique needs and challenges, ensuring that their recommendations were tailored to our organization’s goals and values. With their expert guidance, we refined our messaging and developed a clear and inspiring vision for the future. They were instrumental in helping us craft a strategic plan with actionable next steps that will drive meaningful progress for our organization.”
– HEATHER MCFARLAND, EXECUTIVE DIRECTOR, ALAMO HEIGHTS SCHOOL FOUNDATION
The Outcome:
It has been a joy to watch the Foundation’s momentum build. Since implementing its Strategic Action Plan and refreshed messaging, the Foundation has more than doubled its monthly donor base and hired its first Major Gifts Officer, a direct recommendation from the plan. Foundation grants to the District have grown every year since 2020, and in 2026 the Foundation granted a record $2.5 million to Alamo Heights ISD, its largest gift ever and more than double its 2020 level. That gift alone funds 30 teaching positions. The Foundation’s endowment has grown in parallel, from roughly $6.5 million in 2020 to nearly $13 million today, fueled by disciplined investment performance and a $5 million campaign completed in 2022 to 2023. Building on that momentum, the current $10 million campaign will grow the endowment to $25 million, generating an estimated $1 million in guaranteed annual funding for the District. With this foundation in place, the Foundation is on track to reach its goal of $4 million in annual giving to Alamo Heights ISD by 2030, doubling its impact once again and ensuring the district’s tradition of excellence is funded by design, not by chance.