Meet Our Leaders

John W. Glomb, Jr.
CEO

Quick Facts:

• CEO of Tokio Marine North America & Philadelphia Insurance Companies
• Executive Management Team, Tokio Marine Holdings
• Board of UPenn Rowing and AIM Academy

Mr. John W. Glomb, Jr.'s career began as a management and professional liability underwriter with National Union, an American International Group (AIG) member company. His tenure with AIG consisted of assignments in New York, Chicago, and finally, San Francisco as a Regional Vice President. John also worked at Banc of America Securities LLC for six years in the Financial Institutions Investment Banking practice. He joined Philadelphia Insurance Companies in 2007 as Senior Vice President of the Management and Professional Liability division. In 2009, he took on responsibility for PHLY's entire Underwriting department as Senior Vice President. John was appointed Chief Underwriting Officer in January 2011. He currently serves as President and CEO of PHLY.

In January of 2021, he was appointed CEO of the shared services company, Tokio Marine North America Services (TMNAS). Two years later, he became CEO of TMNA, Inc., the holding company for four Tokio Marine Group companies in the U.S., including PHLY, TMNAS, Tokio Marine America, and First Insurance Company of Hawaii. John also holds the role of Executive Officer within the Executive Management Team at Tokio Marine Holdings, the ultimate parent company of PHLY.

John received a received a B.A. in economics from the University of Pennsylvania and was a four-year member of the nationally ranked Heavyweight Rowing team. He was part of a gold medal-winning U.S. Heavyweight Rowing team at the World University Games. John also received an M.B.A with a concentration in Finance and Strategic Management from the Wharton School of the University of Pennsylvania. He serves on the University of Pennsylvania Rowing Sports Board and the Board of Trustees of AIM Academy - a school (grades 1-12) for children with language-based learning differences. He is also a member of the Breaking Barriers Steering Committee for Children's Scholarship Fund Philadelphia. John and his wife Franny live in Wyndmoor, PA with their four children.

Masahiro (Masa) Koike
TMNA Deputy CEO

Quick Facts:

• Managing Executive Officer, Tokio Marine Holdings
• Chairman, Board of Directors for Tokio Marine America and First Insurance Company of Hawaii
• Board member, 5 Tokio marine Group companies

Mr. Masa Koike has spent his entire professional career with the Tokio Marine Group (TMG), starting as a Reinsurance Trainee in the international reinsurance department at Tokio Marine and Nichido Fire Insurance Company (TMNF) in 1994. After serving various roles and responsibilities at TMNF, he was promoted to Head of Underwriting for the aerospace department in 2014. From there, he moved to the United States as EVP and Head of Operations for the U.S. Branch of Tokio Millennium Re AG (TMR), a subsidiary of TMNF. Masa was serving as Chief Operating Officer and Head of the U.S. Branch by the time TMG sold TMR to Renaissance Re in 2019. He returned to Japan to work again for TMNF, serving as General Manager and Group Leader of the corporate planning department for TMNF until 2021.

In 2021, Masa joined Tokio Marine Holdings, Inc. (TMHD), the ultimate parent company of TMNF, as General Manager and Group Leader of the corporate planning department. He was promoted to Executive Officer and General Manager of the corporate planning department in 2022. Masa currently serves as Deputy CEO for Tokio Marine North America (TMNA) in the United States and as Managing Executive Officer of TMHD in Tokyo, Japan. He has served both roles since 2023.

Masa received his B.A. in law from Keio University in Tokyo, Japan and earned his M.B.A. from Standford Graduate School of Business. He currently serves as a board member of several TMG companies including Tokio Marine North America, Philadelphia Insurance Companies, PURE Insurance, Tokio Marine Canada, and Tokio Marine Seguradora. He is also a chairman of the board for Tokio Marine America and the First Insurance Company of Hawaii.

Caryn Angelson
Chief Legal & Chief HR Officer

Quick Facts:

• Chief Diversity & Inclusion Officer of Tokio Marine Holdings
• Licensed attorney in New York and California
• Executive Management Team, Tokio Marine Holdings

Before her tenure at Tokio Marine North America Services (TMNAS), Caryn practiced at prominent law firms in California and New York. She honed her skills as a litigator, specializing in employment and human resource ("HR") matters. She embarked on her journey with the Tokio Marine Group ("TM" or "Tokio Marine") in 2001 when she joined the HR department. Upon her arrival at TM, Caryn actively engaged with colleagues, including both local employees and a diverse array of expatriates on assignments from Japan. Fast forward to 2011, a decade later, Tokio Marine experienced significant growth, marked by numerous acquisitions and was now considering the establishment of a shared services entity to support its newly acquired U.S. companies. In this pivotal moment, Caryn was entrusted with the role of Chief HR Officer for this emerging entity, TMNAS, overseeing administration, corporate communications and facilities. She also assumed the role of Chief Legal Officer. In 2022, Caryn took on the role of Deputy CDIO (Deputy Chief Diversity & Inclusion Officer) at Tokio Marine Holdings (TMHD). As of April 1, 2024, Caryn was promoted to Executive Officer and Chief Diversity & Inclusion Officer of TMHD.

Caryn received her B.S. in consumer economics and housing with distinction from Cornell University and her Juris Doctorate from Harvard Law School, cum laude. She is a licensed attorney in the states of New York and California. She is also a Client Advisory Board member of Willis Towers Watson and a governing body member for New York Chief Human Resource Officer's communities, Evanta/Gartner. Caryn is married and has a son in high school and a daughter in college; her daughter is on her University's equestrian team.

Karen A. Gilmer-Pauciello
Chief Financial Officer

Quick Facts:

• EVP, CFO and Treasurer of Tokio Marine North America and Philadelphia Insurance Companies
• Certified Public Accountant in the Commonwealth of Pennsylvania
• Member of American & Pennsylvania Institutes of Certified Public Accountants

Prior to joining Tokio Marine North America Services, Karen A. Gilmer-Pauciello began her career as an auditor at PricewaterhouseCoopers LLC in Philadelphia in 1988. She spent seven years as the Vice President & Controller of Admiral Insurance Company and previously held financial management positions at several insurers.

In 2005, Karen joined Philadelphia Insurance Companies (PHLY) as Vice President & Controller before being promoted to Senior Vice President in 2009. She serves as Chief Financial Officer (CFO) at Tokio Marine North America Services (TMNAS). She is also the Executive Vice President, and Treasurer at Philadelphia Insurance Companies (PHLY) and Tokio Marine North America (TMNA). TMNA is the parent company of PHLY and TMNAS, and is a wholly owned subsidiary of Tokio Marine Holdings, Inc. In her current role, Karen is responsible for all financial and tax accounting and reporting, corporate budgeting/planning, treasury activities, and serves as a liaison with the Company's external investment advisors and auditors.

Karen holds a B.A. in accounting and an M.B.A. (finance concentration) from LaSalle University in Philadelphia. She is a Certified Public Accountant in the Commonwealth of Pennsylvania and a member of the American & Pennsylvania Institutes of Certified Public Accountants. She and her husband, who are parents to three adult children, reside in Wyndmoor, Pennsylvania.

Joe Kilroy
Chief Actuarial Officer

Quick Facts:

• Senior Vice President of Tokio Marine North America Services
• Fellow of the Casuality Actuarial Society (FCAS)
• Member of American Academy of Actuaries (AAA)

Mr. Joseph Kilroy had an extensive career at Aon Global Risk Consulting, leading their retail actuarial practice. He joined Tokio Marine North America Services (TMNAS) in September 2021 as Senior Vice President and Chief Actuarial Officer. Joe is responsible for the TMNAS Actuarial team and the services it provides to Philadelphia Insurance Companies (PHLY), Tokio Marine America (TMA), and First Insurance Company of Hawaii (FICOH).

Joe holds a B.A in mathematics from Dartmouth College. He is a Fellow of the Casualty Actuarial Society (FCAS), and a member of the American Academy of Actuaries (MAAA). Joe and his wife Carolyn have three children and live in Drexel Hill, PA.

Rob Middleton
Chief Internal Auditor

Quick Facts:

• Senior Vice President of Tokio Marine North America Services
• M.B.A from Villanova University
• B.A. from Dublin University

Mr. Robert E. Middleton began his career as an external auditor at KPMG in Dublin, Ireland in 1987. He spent 10 years as the Head of Internal Audit at ING Direct, USA. Rob also held previous audit positions at several financial services companies. He joined our team at Tokio Marine North America Services (TMNAS) in 2012 and serves as Senior Vice President and Chief Internal Auditor. He is responsible for providing Internal Audit services for each of the Tokio Marine North America Companies including Philadelphia Insurance Companies (PHLY), Tokio Marine America (TMA), First Insurance Company of Hawaii (FICOH).

Rob holds a B.A. in finance from Dublin University and an M.B.A. in finance from Villanova University. Rob lives in Malvern, PA with his wife, and he is the father of three adult children.

Bob Pick
Chief Information Officer

Quick Facts:

• Group Deputy Chief Information Officer for Tokio Marine Holdings
• Executive sponsor for TMNAS Diversity Equity Inclusion and Belonging (DEIB) Council
• Chair for the Board of Trustees of the Philadelphia Youth Orchestra Music Institute

Mr. Robert Pick joined Tokio Marine North America Services (TMNAS) in 2014 after 16 years in major media and telecommunications, as well as an audit and consulting stint with PricewaterhouseCoopers. He is a regular conference and podcast speaker on topics ranging from Insurtech and insurance trends, legacy modernization, and most recently, Generative AI (Artificial Intelligence). As the Executive Vice President & Chief Information Officer at TMNAS he leads our team in providing a full suite of digital and technology services to Tokio Marine North America companies, as well as point services including Business Continuity Management and Information Security to Tokio Marine sibling companies such as Reliance Matrix and Tokio Marine Mexico.

Bob is also the Group Deputy Chief Information Technology Officer for Tokio Marine Holdings, working to support Tokio Marine companies worldwide. Additionally, he is the executive sponsor for the TMNAS Diversity Equity Inclusion and Belonging (DEIB) Council.

Bob is the Chair of the Board of Trustees of the Philadelphia Youth Orchestra Music Institute. In the past, Bob served as a member of the Advisory Board for the Johns Hopkins University Press, the Client Advisory Board for NTT, the Strategic Advisory Board for Guidewire, the CIO (Chief Information Officer) Council for Blumberg Capital, and the Customer Advisory Board for Duck Creek. He holds a B.A. from McDaniel College, Phi Beta Kappa, an M.A. from Cornell University and completed an additional two years of doctoral coursework and reading. Bob resides in Perkiomenville, PA with his wife, lazy basset hound, and sometimes resident daughter who is a junior in college.