Speaking, Moderating, and Facilitation
Moderated Conversations, Panels, and Interviews
The most compelling conversations begin with great questions and the willingness to listen.
Drawing on more than a decade of interviews with philanthropists, nonprofit leaders, innovators, and changemakers, Jay brings curiosity, preparation, and a conversational style to the stage. Whether interviewing a distinguished guest, moderating a panel, or facilitating a public forum, he creates an environment where people feel comfortable sharing their experiences, perspectives, and ideas.
From intimate one-on-one conversations to major conference stages, Jay helps audiences connect with the people and stories shaping our world.
Keynotes and Plenaries
Jay Frost brings insight, energy, and decades of experience to keynote presentations that challenge assumptions, spark new ideas, and inspire action. Each presentation is tailored to the audience, the occasion, and the opportunities ahead.
Stand Out!
Are you still pursuing your biggest ambitions, or has the daily grind gotten in the way? In this engaging and thought-provoking presentation, Jay challenges audiences to rediscover what matters most, confront the obstacles holding them back, and make better use of their most precious resource: time. It's an invitation to think bigger, act with greater purpose, and stand out in work and life.
Faster, Smarter, Greater: The Future of Donor Intelligence
Artificial intelligence, predictive analytics, and increasingly sophisticated data tools are transforming fundraising. But does having more information make us better at connecting with people? Drawing on decades at the intersection of philanthropy, technology, and human relationships, Jay explores how organizations can harness new tools without losing sight of what drives generosity: trust, empathy, and a shared sense of purpose. The challenge isn't simply to become faster and smarter. It's to become greater at what we do.
General Sessions, Breakouts, and Workshops
Jay combines practical insights, fresh perspectives, and engaging storytelling to create sessions that inform, challenge, and inspire. From emerging technologies and fundraising strategy to leadership and human connection, each session encourages participation and provides ideas audiences can put to work.
Beyond the Prompt: AI, Human Judgment, and the Future of Fundraising
Artificial intelligence is moving beyond writing appeals and answering questions to reshaping how nonprofits identify donors, manage relationships, make decisions, and organize their work. But which applications deliver real value, and where must human judgment remain in control? Jay explores the rapidly evolving opportunities and risks of AI, from predictive analytics and intelligent agents to data privacy, organizational readiness, and donor trust. Participants will discover practical ways to evaluate emerging technologies, strengthen their teams, and put AI to work without losing the human connections at the heart of philanthropy.
The Power of Questions: Listening, Leadership, and Human Connection
What makes a conversation meaningful? And how can asking better questions change the way we understand and influence others? Drawing on hundreds of interviews with philanthropists, leaders, innovators, and changemakers, Jay explores the art of asking questions that reveal motivations, challenge assumptions, and create deeper connections. Through practical examples and interactive discussion, participants will discover how curiosity, thoughtful inquiry, and genuine listening can transform relationships and open unexpected possibilities.
Seal the Deal: The Psychology of Trust and Transformational Giving
Why do people give, and what inspires them to make extraordinary commitments? Jay explores the psychology of trust, the motivations behind generosity, and the relationships that make transformational philanthropy possible. Drawing on research, real-world examples, and decades of fundraising experience, this session examines how to build credibility, uncover donor aspirations, and move from initial engagement to lasting philanthropic commitment.
The Six Pillars of Fundraising Success: Meeting the Challenges of Our Times
Successful fundraising demands more than great solicitation skills. It requires strategic thinking, technological fluency, emotional intelligence, and a commitment to ethical practice. In this interactive session, Jay explores six essential pillars of fundraising success, from identifying prospective donors and building authentic relationships to inspiring generosity, engaging volunteers, and navigating a rapidly changing philanthropic landscape. Participants will explore how to strengthen their fundraising practices while remaining true to their organizations' missions and values.
Power Prospecting: Finding Your Major Gift Opportunities of the Future
Where will your next major donors come from? Jay explores how to identify individuals with the capacity and inclination to make transformational gifts, drawing on advances in prospect research, wealth intelligence, and data analytics. Whether preparing for a capital campaign or expanding major gift fundraising, participants will discover new ways to find, understand, and connect with the people who can make their missions possible.
Tales from the Crypt: Horror Stories of Fundraising
From spectacular missteps to astonishing lapses in judgment, fundraising has produced its share of unforgettable disasters. Jay brings some of the field's funniest, strangest, and most cautionary tales to life, revealing what happens when good intentions go terribly wrong. Equal parts entertainment and education, this lively session offers lessons in judgment, ethics, and human nature that participants won't soon forget.
Board Retreats
An effective board retreat creates space for honest reflection, fresh thinking, and shared purpose.
Jay works with board and staff leadership to design and facilitate retreats tailored to each organization's mission, culture, and challenges. Through thoughtful questions, candid conversation, and collaborative exploration, participants assess where they stand, clarify where they want to go, and identify the steps needed to get there. The goal is a more engaged, aligned, and energized leadership team, ready to turn shared ambitions into meaningful action.