James L. Holmes, Jr.
Chief Executive Officer
Jim Holmes founded Sentinel knowing that structured, measurable, and smart processes drive results. With over 20 years of professional experience in positions including Controller, Vice President of Finance, Chief Financial Officer, Director of Operations, and Chief Operating Officer at companies in the United States and abroad, Jim possesses the industry insight required to help clients protect investments, assets, and businesses.
As CEO, Jim focuses on Sentinel’s overall strategy and direction to ensure alignment with the firm’s vision. He cultivates and maintains strong relationships with clients and stakeholders while identifying new business opportunities, driving innovation, and fostering a culture of continuous improvement.
Nicole Wise, CPCU, CRM, CIC
President, Sentinel Risk Advisors
With more than 30 years of commercial insurance marketing experience, Nicole brings extensive knowledge and leadership to Sentinel spanning account analytics, client service plan customization, placement strategies, and customer engagement.
Nicole assumed the role of President for both Sentinel Risk Advisors and Sentinel Risk Performance Group on June 1, 2025. These divisions collectively deliver innovative services and solutions for commercial and personal risk management in addition to loss prevention, transportation fleet consultancy, and claims advocacy.
As President, Nicole oversees all aspects of the divisions’ operations, from sales and marketing to client service and administration, ensuring the firm meets its financial and operational goals.
Rob Krieg, JD, CEBS
Managing Director, Employee Benefits
Rob joined Sentinel in spring of 2023 as the firm’s Managing Director of Employee Benefits. Owner of a law degree and recognized as a Certified Employee Benefits Specialist (CEBS), Rob serves as one of the lead consultants for Sentinel Benefits Consulting.
Rob previously worked as an Area Vice President where he helped clients design, implement, and manage the employee benefit program that best met their organizational needs for recruiting, retaining, and rewarding employees. This followed more than 10 years of experience gained at Hill, Chesson & Woody first as the firm’s Compliance Officer, and then as a Principal Health and Welfare Consultant. The Richmond University graduate earned his law degree at the University of Maryland Law School and began his career as Assistant State’s Attorney at the Baltimore County Government.
Will Rike, CPA
Chief Financial Officer
As Chief Financial Officer, Will is responsible for managing the firm’s financial activities, monitoring cash flow, and evaluating strengths and weaknesses to ensure financial prosperity. In addition, Will oversees the Human Resources and Information Technology departments.
Will has a wealth of experience in accounting spanning over 20 years across multiple sectors including hospitality, financial services, international private equity, and investment banking.
