Caryn Siebert: The Powerhouse Who Paved the Way  

There are leaders, and then there are trailblazers who break barriers, turn around, extend a hand, and pull others up with them. Caryn Siebert is so much more than a force in the insurance industry; she is the force. With a career spanning nearly 40 years, she has risen, endured, shattered glass ceilings, and ensured others have a clearer path to follow. Her influence is unmatched, her support unwavering, and her legacy? It continues to unfold in the most dazzling way possible. 

As we celebrate Women's History Month 2025, we must honor this glittering leadership, mentorship, and resilience icon. This woman has made it to the top and is making sure others do, too. 

A Year of Triumphs: When Momentum Becomes Legacy 

For most professionals, earning a CLM (Claims & Litigation Management Alliance) Lifetime Achievement Award would be the pinnacle of a career. But for Caryn, it was just the beginning of a year filled with groundbreaking recognition. In 2024, she was honored with the ALM/PropertyCasualty360 Luminary Award for her work across charities, mentorship, and DEI initiatives. And just when she thought the whirlwind of accolades had peaked, the Insurance Business America Hall of Fame came calling. 

“After picking myself off the floor and asking the caller to repeat what he said, you can only imagine the joy—both personally and professionally—of this honor,” Caryn said. 

But the most Caryn thing about this moment? Instead of basking in the spotlight, she turned it outward, crediting the employees and mentors who shaped her journey. The world may celebrate her achievements, but Caryn sees them as fuel to uplift others, push boundaries, and redefine what is possible for women in this industry. 

Mentorship: The Heartbeat of Her Leadership 

Caryn’s career is a masterclass in leadership. Aside from the roles she has held, Caryn’s leadership is showcased by the people she has elevated along the way. From her involvement with RISE (Rising Insurance Star Executives) to championing DEI initiatives, Caryn has actively shaped the future of this industry. Caryn is also much more than a participant in the Claims and Litigation Management Alliance; she is a driving force, actively mentoring and fostering a culture of learning and growth. Her passion for education and access led to establishing the Combined Claims Conference (CCC) Scholarship Program, ensuring that the next generation of claims professionals has the resources to succeed. Outside the insurance industry, Caryn’s impact continues with the California State University Fullerton Caryn Seibert Business Writing Scholarships. 

The impact is clear: her mentees are rising. Caryn has nominated and supported professionals for awards, promotions, and executive roles, proving that true leadership is more than personal success. True leadership creates, develops, and illuminates pathways for others to shine. 

Lessons in Influence: The Power of Relationships 

With all her accolades, what’s the biggest lesson Caryn has reinforced this year? 

Relationships matter. 

More people than ever have reached out to her, seeking advice, mentorship, and career transitions. In a time when professional landscapes are shifting at lightning speed, Caryn remains a constant source of guidance, wisdom, and opportunity. 

Caryn watches as former colleagues have circled back, now in positions of power, recognizing the value of a trusted partner in navigating complex industry challenges. Her vast network is deeply rooted in genuine connections, mentorship, and an unwavering belief in the people she supports. 

Her advice to professionals? Don’t wait until you need a new role to network. Build relationships proactively, nurture them, and invest in the success of others. 

The Evolution of a Visionary: What’s Next for Caryn Siebert? 

At a time when many are eyeing retirement, Caryn is doubling down on impact. 

While she embraces new experiences, spends precious time with her mother, and continues her adventures, she remains deeply committed to the industry. She sees the next wave of transformation unfolding—through AI, data analytics, and technology-driven innovation—and is excited to help shape it. 

This shift will create new roles, opportunities, and even higher compensation for claims and underwriting professionals. Caryn is ready to help the next generation step into these game-changing positions. 

Caryn is in no way slowing down—she is amplifying. 

Caryn’s Golden Rule: Lead With Impact, Leave a Legacy 

Caryn’s career is so much more than what she has accomplished. Caryn’s legacy is about the footprints she has left for others to follow. She’s been a CEO, a C-suite executive, a legal expert, and a thought leader. The most important role, she IS a champion for people. Caryn transformed companies, launched initiatives, and changed lives through her mentorship, philanthropy, and leadership. She built a legacy that will endure long beyond her time in the industry—a legacy that says success isn’t just about climbing higher; it’s about reaching back and lifting others with you.  

And let us be real. Caryn has not just built a legacy, Caryn Seibert is a legacy. 

Her advice? No two journeys look the same. Embrace the detours, lean into the challenges, and never stop paying it forward. 

Caryn Siebert: A Name That Will Echo for Generations 

Caryn’s name will forever be etched in the history of the insurance industry—not just for her achievements but for the way she made people feel, the opportunities she created, and the culture of mentorship she cultivated. 

She is a glitter sister, a brilliant form of resilience, and a leader who redefines what’s possible. 

As we celebrate Women's History Month 2025, there is no better moment to say: Caryn Siebert, you didn’t just make it—you changed the game for all who come after you. 

Thank you. 

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