Jay Goulart is the founder of Big Philanthropy and is recognized nationally as a leading fundraising strategist, solicitation coach, and advancement innovator. Over the past 20 years, he has served on the front lines of independent school fundraising, personally managing more than 2,000 donor solicitations ranging from annual support to transformational philanthropy.

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Jay is a CASE Crystal Apple recipient for teaching excellence and a CASE Laureate. He is often referred to as “the consultant to the consultants” for his work training advancement professionals, school leaders, and campaign volunteers in the art and science of philanthropic conversations, as well as for his uniquely insightful analytic models.

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In 2013, Jay became the first nonprofit professional invited by IBM to help design a philanthropic application utilizing Watson. Long before artificial intelligence became mainstream, he recognized its potential to transform relationship-driven fundraising.

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Today, Jay has developed a suite of AI-powered tools designed specifically for independent schools and advancement teams. These innovations include:

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• Mastering the Ask — an AI-supported solicitation training platform designed to help fundraisers and volunteers build confidence and effectiveness in high-stakes donor conversations.

• The Philanthropic Bridge Framework — a relationship-centered methodology that helps advancement professionals move donors thoughtfully from surface-level engagement toward trust, depth, partnership, and legacy-level philanthropy.

• The Alignment Engine — a next-generation relationship intelligence platform that measures donor readiness, tracks relationship movement, and provides strategic insight that makes traditional moves management alone increasingly obsolete.​

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Jay’s work challenges many of the legacy assumptions within fundraising through innovative data analysis and relationship intelligence frameworks that question what the sector has measured — and valued — for decades. His work is grounded in a belief reinforced by mentors throughout his career: the quality of the questions we ask ultimately determines the quality of the outcomes we achieve. For more than fifty years, philanthropy has largely measured activity volume — visits, proposals, moves, and transactions — while often failing to assess the depth, timing, trust, and emotional readiness that actually drive transformational giving. Jay’s work argues that transformational philanthropy is not primarily created by the quantity of activity, but by the quality, sequencing, and human depth of relationships. His frameworks and analytics challenge organizations to move beyond legacy metrics and begin asking more meaningful questions about connection, alignment, trust, and relationship movement — the very factors that often determine whether extraordinary philanthropy occurs.