LEDGEBROOK INSURANCE - Key Persons


Calvin Webster

Job Titles:
  • Staff Software Engineer
Calvin has 15 years of software engineering experience and has worked in small startups with complex scheduling software to large goverment contractors, leading the development of the UI for large scale data processing applications. He loves using technology to help solve problems and is passionate about building quality software. In his spare time he enjoyes playing Magic: The Gathering, surfing and hanging with his family. Calvin currently lives in Charleston, SC with his wife and 4 children. Calvin holds a B.S. in Molecular Biology from the University of North Carolina at Pembroke.

Gage Caligaris - CEO, Founder

Job Titles:
  • CEO
  • Founder
Prior to entering the world of insurance, Gage used his degree in Applied Mathematics from Harvard to trade exotic commodity derivatives at Barclays. His insurance career started in the Actuarial program at Liberty Mutual where he became the fastest person ever to pass the Casualty Actuarial exams. From there, various management positions culminated in the role of Senior Director of New Mobility Products where he spearheaded growth from <$50M to >$450M in GWP. His unique combination of entrepreneurial drive & deep insurance industry expertise represent the foundational bedrock of Ledgebrook. Gage lives in the Greater Boston area with his wife and two children.

Jeff Snook

Job Titles:
  • Vice President - Actuarial
Jeff brings 30+ years of experience in the insurance industry working in Actuarial and Product Management roles. Jeff's career began with Crum and Forster in their Actuarial department. His role included pricing for Personal and Commercial lines of business. Crum and Forster's re-structuring in 1993 resulting in the creation of Coregis Insurance Company. Jeff was part of a select group invited to work at newly formed Coregis Insurance Company. An excellent opportunity to learn from industry leaders brought in with goal to sell the company. While working as a pricing actuary for the Property & Casualty Division, Jeff worked closely with Marketing, State Filing, Underwriting, and claims departments. The Business model broke down legacy silo barriers between departments and facilitated strong collaboration in product development / management. After Coregis was sold, Jeff left to work as pricing actuary for IFG Companies. IFG Companies, is a privately owned property casualty insurer with focus excess and surplus lines business. At IFG Companies Jeff was able to take lessons learned from Coregis and work closely with Underwriting, IT, and Claims departments. In addition to providing actuarial support for Primary General Liability, Commercial Property, and Excess Liability lines of business, Jeff also focused on Portfolio management for both Binding Authority business as well as Brokerage operations. Jeff holds a B.S. in Actuarial Science from Lebanon Valley College and resides in Elon North Carolina with his wife Lynn.

John Mullen

Job Titles:
  • Chief Underwriting Officer - General Liability
John has experience within multiple facets of the insurance industry. He began his career in Underwriting within the Excess & Surplus lines space prior to spending time as a Retail Insurance Broker. From there, he's had the opportunity to represent multiple regional and global insurance carriers in various Underwriting and Underwriting Leadership roles throughout his career. John joins Ledgebrook most recently from Liberty Mutual where he led the strategy, development and build out of appetite, risk tolerance and profitability in the Large Casualty space, a portfolio comprising $1Billion in GWP. Previous to that, John led both Industry and Underwriting company wide initiatives during his career at Zurich North America in their Middle Markets segment. He holds dual Bachelor degrees in Risk Management & Insurance and Financial Management with a minor in Business Administration. John holds a MBA in Insurance & Risk Management as well as the CPCU and AAI designations. He's spent time as a CPCU Chapter Past President, but most important to him, he enjoys spending his time with his wife and two daughters in Michigan.

Leslie Achor

Job Titles:
  • Executive Underwriter
Leslie brings with her 30+ years of experience in the insurance industry. Roles ranging from the retail side as a licensed insurance agent to the company side in field underwriting to underwriting leadership. Her most recent 20+ years have been spent on the E&S side of the business, spending most of those years with Lexington Insurance Company. Starting out as a Casualty Underwriter and culminating as Casualty Branch Manager of the New Orleans office, building extensive experience in primary and excess casualty business for Energy, Construction and Products risks of all sizes. Leslie is a native of the New Orleans metropolitan area, where she currently resides with her husband and son, and a grown daughter nearby.

Marlon Orozco

Job Titles:
  • Senior Underwriter
Marlon first started his insurance career with Sompo International formerly known as Endurance in 2014. Upon entry he quickly went up the ranks from back-office support to Underwriting for the E&S Primary Casualty Team. His focus was on Manufacturing, Contracting, Hospitality and Real Estate. In addition to underwriting, he was responsible for assisting the team with decision making reports to keep track of profitability using an analytical approach. He also worked in conjunction with multiple departments in order to create efficiency within the E&S Primary Casualty through an offloading process. This allowed the team to grow efficiently with proper administrative support within other departments. In addition, he managed an MGA book of business that consisted of Amusement Parks and Motorsports accounts. He holds a B.S. in Finance from William Paterson University in Wayne, NJ. His biggest enjoyment is spending time with his wife and two boys in Pennsylvania.

Michael McMyne

Job Titles:
  • Chief Claim Officer
Mike began his career as a Property & Casualty insurance claim professional in 1979 with the Safeco Insurance Company as a multi-line outside claims adjuster. During his diverse career he has managed most aspects of a property and casualty claim operations from personal and commercial auto, large national accounts, environmental and chemical exposure, catastrophic injuries, technical training, quality assurance, litigation management and excess & surplus lines property and casualty claims. Mike holds a Bachelor of Science degree in Law Justice from Glassboro State College (now Rowan University) and a JD from Western New England University School of Law. Mike lives in Western Massachusetts with his wife and has three adult daughters and seven grandchildren.

Nathan Hall - CTO

Job Titles:
  • Chief Technology Officer
Nathan started his career with PricewaterhouseCoopers working in the Capital Markets and Accounting Advisory group. He left to return to his true passion of coding and co-founded an accounting SAAS product for law firms. He then spent the better part of the next decade as a principal engineer in a variety of industries, including healthcare and fintech. He helped scale small engineering teams from the tens to the hundreds, and helped craft the architectural vision those companies rely on. Nathan holds his M.S. in Accounting and B.S. in Commerce with a concentration in Finance, both from the University of Virginia. He lives in Birmingham, AL with his wife and two sons.

Nicolette Oster

Job Titles:
  • Senior Underwriter
Six years ago, Nicolette changed career paths, switching from a role as an Executive Assistant to an entry level Assistant Underwriting position at a managing general agency and wholesale broker. After the first year in her new career, she took an opportunity to relocate her family from Minneapolis, MN to Denver, CO to assist with establishing a new office. She continued her career with both Northern States Agency and Ringwalt & Liesche Co., members of the Berkshire Hathaway family of companies, where she placed small to medium-sized commercial lines business while training new hire assistants and underwriters. Most recently she completed the CPCU designation. She currently resides in the Denver area where she is inspired daily by her husband and their two small children. They keep her very busy!

Steve Mills

Job Titles:
  • President - E & S
Steve brings 30+ years of insurance industry experience to Ledgebrook. His experience spans multiple distribution channels and segments of the industry, including standard lines package, large account casualty, casualty facultative reinsurance and excess & surplus lines. Steve's career progression includes a variety of field production, product line management and leadership roles. His most recent experiences have focused exclusively within the E&S space where he's held E&S leadership roles of increasing responsibility at both large and small organizations. Steve is passionate about building and leading underwriting teams that deliver market relevant solutions coupled with profitable growth. Steve holds a Bachelor of Science in Business Administration from The Ohio State University with dual concentrations in Risk Management & Insurance and Finance. He currently lives in the Greater Atlanta area with his wife and two daughters.