Pete du Pont Freedom Foundation (PDFF) is proud to announce Robert L. Siegfried, Jr., the CEO and Founder of The Siegfried Group, as our 2025 Honoree. A visionary entrepreneur, steadfast community advocate, and devoted believer in individual responsibility and principled leadership, Rob exemplifies PDFF’s mission to empower people and transform communities.
Rob’s leadership journey began more than four decades ago when he set out to redefine helping financial executives not only become better leaders, but also live with greater purpose, clarity, and conviction.
His work extends far beyond boardrooms and balance sheets. Rob created a name for himself through philanthropy, mentorship, innovation, and public service, and shaped the lives of thousands, always guided by a core belief that personal accountability is the foundation of true success and that effective leadership starts from within.
A Career Rooted in Conviction and Hard Work
Rob began his professional career at Arthur Young (now Ernst & Young) in 1981, working in Baltimore and building a stable and what he would call “predictable” path to becoming a partner. In 1988, with a clear vision of doing things differently, he left the safety of his traditional accounting career to found The Siegfried Group in his hometown of Wilmington, Delaware.
It wasn’t an easy start. Rob had a lot at risk financially, and failure was not an option. He recalls sitting on the floor of his first office, phone in one hand, phone jack in the other, as he waited for furniture to arrive. His wife, Kathy, left her job to join him, as did a close colleague. Together, they built what Rob describes as a grassroots operation driven by values and purpose rather than resources or reputation.
His goal was simple: to create a firm that provided not just financial guidance but emotional fulfillment for its clients, employees, and stakeholders. “I wanted the firm to provide emotional gratification to all the stakeholders, including myself, my clients, and my employees,” Rob explains. “Emotional gratification became part of my definition of the firm’s success.”
Today, The Siegfried Group serves many of the Fortune 1000 companies in the United States through its 19 offices, has more than 1,300 employees, and continues to help CFOs and executive teams clarify what matters most — then delivers elite financial talent to make it happen.
From those humble beginnings to now, Rob consistently focuses on what truly matters — not just profit, but the ability to make lasting impact.
Success: A Matter of Character, Freedom, and Dreams
For Rob, success isn’t defined solely by titles or profits; it is measured by the integrity of one’s character, the fulfillment derived from living in alignment with personal values, and the freedom to pursue one’s dreams relentlessly. “I’ve come to realize that everybody defines success differently,” he says. “To me, success is what’s going to bring you emotional gratification and fulfillment.”
Rob believes that freedom, responsibility, motivation, and inspiration are all deeply connected. “If you delegate authority to someone else, then your results are not going to be consistent with what your dreams are. You need to have the freedom to pursue whatever your dream is, because that’s where you find the energy that’s needed to be more disciplined, humble, ambitious, courageous — all the things that you need to embrace to be successful.”
Whether it was walking away from a secure career, making profound personal decisions, or founding a company with little more than ambition, grit, and access to a phone jack, Rob has always trusted his inner compass.
Helping Students Lead
Rob always understood the power of leadership. As a young man, he looked up to his parents, business leaders, and mentors, and quickly came to a realization: If I want my business to succeed, I need to become a better leader.
At first, that meant driving results, making smart decisions, and setting direction. But over time, Rob’s definition of leadership shifted.
“I realized that leadership is personal,” Rob shared. “I can’t lead anyone or anything well unless I’m first effective at leading myself.”
That insight launched a deeper journey. Rob studied successful leaders, explored his own values, and focused on becoming the most authentic, impactful version of himself.
His passion for leadership development soon turned outward. In 2016, after expressing concern about a lack of direction and ambition he saw in young people, his daughter Jacqueline offered a simple suggestion: “Dad, the most impactful thing you could do for kids is talk to them.”
That one conversation led to the creation of Siegfried Youth Leadership Program® (SYLP), an immersive program for 8 – 12th grade students that focuses on topics such as individual leadership, entrepreneurship, and creating bigger futures. SYLP is supported through a close partnership with Rob and Kathy’s alma mater, the University of Delaware (UD), as well as Junior Achievement of Delaware.
This close partnership is rooted in personal history. Having developed emotionally-gratifying relationships within the UD community, and to honor the corresponding impact these relationships have had on their lives and success, Rob and Kathy have donated more than $75
million to UD for various initiatives and programs. Initially, they pledged more than $6 million for the Siegfried Initiative for Entrepreneurial Leadership, which is led by the Center for Economic Education and Entrepreneurship (CEEE) and Horn Entrepreneurship.
Most recently, they donated an additional $71.5 million to fund the creation of Siegfried Hall, an impressive, state-of-the-art, student-centric learning space that will maximize experiential learning and collaborative programming. The gift will also establish the Siegfried Institute for Leadership and Free Enterprise, an idea lab that will research and teach the capabilities and characteristics of effective leadership and explore the vital role that the basic principles of limited federal government, rule of law, and free enterprise play in supporting individual freedoms and developing effective individual leadership.
As a proud UD alumnus, Rob has maintained a decades-long relationship with the University. He has received the Alumni Award of Excellence, been inducted into the UD Wall of Fame, and served 20 years on the Alfred Lerner College advisory board, including five years as the Chair. “It was a very humbling experience realizing how many professors helped me,” Rob recently reflected. “My time at UD and the people, professors, and relationships I built there were very instrumental to me.”
In addition to the entrepreneurship and leadership programs at UD, Rob pledged $6.5 million to Evans Scholars Foundation, an organization that provides deserving golf caddies with transformational college educational experiences. Around the same time, he also made an ongoing commitment to Saint Edmond’s Academy, consisting of full tuition assistance for 16 underprivileged students.
Outside of Delaware, Rob and Kathy have a close affinity for High Point University (HPU), their sons’ alma mater, contributing more than $2 million to build the Siegfried Leadership Fellows Program.
Join Our Mission
As the 2025 Freedom Award Honoree, Rob is honored to be recognized and grateful for the opportunity to share his perspective.
At the core of his leadership philosophy are ambition, courage, humility, and love. These aren’t just character ethic traits he talks about, but values he works to live by and instill in others. “Personal growth is never just personal,” Robs shares. “Improving your life, improves the lives of everyone around you.”
As we celebrate Rob’s impact, we invite you to join us in carrying PDFF’s mission forward.
We are currently seeking additional sponsors, donors, and champions to help bring the next generation of bold ideas to life. Whether you’re interested in underwriting development services or making a financial contribution, your support plays a vital role in shaping a stronger, more inclusive economy in Delaware.
For more details on getting involved with PDFF, contact Lynn Roberts at [email protected]. Your contribution helps invest in strategic, practical resources to position businesses for success, ultimately creating jobs and improving communities across Delaware.
Attend the 2025 Freedom Award Event
The Pete du Pont Freedom Foundation is honored to celebrate bold innovation and the enduring legacy of Governor Pete du Pont with the 2025 Pete du Pont Freedom Award. The award will be bestowed during a ticketed event on Wednesday, September 10, at the iconic Hotel du Pont, bringing together Delaware’s most influential business leaders for an evening of connection and inspiration. Visit the event registration page to secure your tickets.