Boston, June 17, 2026 — Founder and CEO, Gage Caligaris of Ledgebrook was named an EY US Entrepreneur Of The Year® 2026 New England Award winner.
After earning a degree in Applied Mathematics from Harvard and trading derivatives at Barclays, Gage entered the insurance industry through Liberty Mutual's actuarial program, becoming the fastest person ever to complete the Casualty Actuarial exams. He later led Liberty Mutual's New Mobility business, growing it from under $50 million to more than $450 million in premium.
That combination of technical expertise, industry knowledge, and entrepreneurial vision became the foundation for Ledgebrook, which is modernizing the global specialty (re)insurance market through technology, AI, and exceptional service. By bringing together top insurance and engineering talent and fostering a culture where employees share directly in the company's success through equity ownership, Ledgebrook has built a differentiated platform focused on delivering outstanding outcomes for brokers and customers alike.
“I am honored to receive this recognition. While it is a personal achievement, it is also a reflection of the incredible team, customers, and partners who have helped make our success possible. I am proud of what we have accomplished together and grateful for the opportunity to lead such a talented organization. This award is a celebration of our shared journey and the exciting opportunities ahead.”
- Gage Caligaris, Founder and CEO of Ledgebrook
Now in its 41st year, the Entrepreneur Of The Year program honors business leaders for their ingenuity, courage and entrepreneurial spirit. It celebrates original founders who bootstrapped their business from inception or raised outside capital to grow their company, transformational CEOs who infused innovation into an existing organization to catapult its trajectory and multigenerational family business leaders who reimagined a legacy business model to strengthen it for the future.
Regional winners were chosen by an independent panel of past winners, top CEOs and business leaders. Judges assessed candidates on long-term value creation, entrepreneurial spirit, purpose-driven commitment, and significant growth and impact.
As a New England award winner, Gage will now be considered by the national judges for the Entrepreneur Of The Year 2026 National Awards, which will be presented in November at the annual Strategic Growth Forum®, where high-growth CEOs, Fortune 1000 executives and investors converge to shape the future of business. The National Overall Award winner will move on to compete for the EY World Entrepreneur Of The Year™ Award in May 2027.
The Entrepreneur Of The Year program has recognized the leadership of entrepreneurs such as:
JasonMcGowan,
Crumbl Cookies
Reid Hoffman | Jeff Weiner,
LinkedIn Corp.
Saeju Jeong,
noom
Allison Ellsworth | Stephen Ellsworth,
poppi
Jitendra Mohan | Sanjay Gajendra | Casey Morrison,
Astera Labs
Carolyn Rafaeilian,
Alex and ani
John V. Oyler,
BeOne Medicines
Shelly Ibach,
Sleep Number
Howard Schultz,
Starbucks Coffee Company
Holly Thaggard | Amanda Baldwin,
Supergoop!
Jodi L. Berg,
Vita-Mix Corporation
Michael Happe,
Winnebago Industries
CarlosVentura,
Feast & Fettle
Bill Creelman,
Spindrift Beverage Co.
Kate Haviland,
Blueprint Medicines
Sponsors
Founded and produced by Ernst & Young LLP, the Entrepreneur Of The Year Awards include presenting sponsors PNC Bank, Cresa, LLC, Marsh Risk, SAP, and the Ewing Marion Kauffman Foundation. In New England, sponsors also include regional Platinum sponsor, DLA Piper, regional Gold sponsor, ADP, and regional Silver sponsor, Stagedge.
About Entrepreneur Of The Year®
Founded in 1986, Entrepreneur Of The Year® has celebrated more than 11,000 ambitious visionaries who are leading successful, dynamic businesses in the US, and it has since expanded to nearly 60 countries and territories globally.
The US program consists of 17 regional programs whose panels of independent judges select the regional award winners every June. Those winners compete for national recognition at the Strategic Growth Forum® in November where national finalists and award winners are announced. The national overall winner represents the US at the World Entrepreneur Of The Year® competition. Visit ey.com/us/eoy.
EY | Building a better working world
EY is building a better working world by creating new value for clients, people, society and the planet, while building trust in capital markets.
Enabled by data, AI and advanced technology, EY teams help clients shape the future with confidence and develop answers for the most pressing issues of today and tomorrow.
EY teams work across a full spectrum of services in assurance, consulting, tax, strategy and transactions. Fueled by sector insights, a globally connected, multi-disciplinary network and diverse ecosystem partners, EY teams can provide services in more than 150 countries and territories.
All in to shape the future with confidence.
EY refers to the global organization, and may refer to one or more, of the member firms of Ernst & Young Global Limited, each of which is a separate legal entity. Ernst & Young Global Limited, a UK company limited by guarantee, does not provide services to clients. Information about how EY collects and uses personal data and a description of the rights individuals have under data protection legislation are available via ey.com/privacy. EY member firms do not practice law where prohibited by local laws. For more information about our organization, please visit ey.com.
© 2026 Ernst & Young LLP.
All Rights Reserved.
ED None
This material has been prepared for general informational purposes only and is not intended to be relied upon as accounting, tax, legal or professional advice. Please refer to your advisors for specific advice.
About Ledgebrook
To learn more about Ledgebrook and opportunities to join our team, please visit www.ledgebrook.com or email info@ledgebrook.com.
