Preparing the Next Generation to Thrive with Ashley Birtwell, Head of School at Sewickley Academy
OCTOBER 6, 2026Success doesn't always follow a straight path, and sometimes the most meaningful opportunities are the ones you never planned for.
“If we all waited until we felt entirely prepared, my goodness, we'd be stalled in our careers.”
Greg Weimer sits down with Ashley Birtwell, Head of School at Sewickley Academy, for a conversation about leadership, fulfillment, resilience, and what it takes to prepare the next generation for a rapidly changing world.
Ashley’s journey has taken her from studying organizational behavior at MIT to working abroad in India and ultimately finding her calling in education. Along the way, she learned the value of embracing unexpected opportunities, having the courage to step outside your plan, and staying connected to what brings purpose to your life. Today, those lessons shape how she leads and how she thinks about helping young people develop the confidence, relationships, and critical-thinking skills they will need for the future.
In this episode, gain insights on:
- Outside the plan: why some of life's greatest opportunities come from being willing to step outside your plan
- Achievement vs. fulfillment: how to recognize when achievement isn't the same as fulfillment
- Always learning: why continuous learning and investing in yourself are essential to personal and professional growth
- A changing world: how AI, technology, and social media are changing the way young people learn, connect, and prepare for the future
- Let them struggle: why allowing kids to struggle can help build grit, confidence, and problem-solving skills
- Connection endures: how relationships, empathy, and human connection remain essential to meaningful leadership and a lasting legacy
Greg Weimer
Chief Executive Officer, Chairman — Confluence Financial Partners
Greg is passionate about helping individuals and families maximize their lives and legacies. His journey began in 1986 as a financial advisor, and he went on to join American Funds Distributors in 1993, where he became senior vice president and served on the Board of Directors.
Greg attended the University of Pittsburgh, where he earned a business degree with a concentration in computer science and mathematics. He serves on the Board of Directors of UPMC Children’s Hospital of Pittsburgh, is Vice Chair of the Children’s Hospital of Pittsburgh Foundation, and is a Knight of the Order of Malta.
He was named Italian Man of the Year by the Pittsburgh Italian Scholarship Fund in 2024 and received the Community Caritas Award from Catholic Charities of the Diocese of Pittsburgh in 2025.
