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Our associates are our greatest asset, and we promote a culture of high performance that encourages career and professional development.


Only big insurance brokers can supply everything clients need. Only small ones offer the personalized service they deserve. Hilb Group is the best of both. We grow by partnering with entrepreneurial local brokers who deliver old-fashioned personal service. We support you with the valuable resources of a big player. Our clients and partners get more that way – the Hilb Difference.

“Each new partner brings increased opportunities and enhanced expertise, local community and market presence, and well-developed client relationships, which are the key to fostering growth and providing innovative resources and solutions for all of our associates and customers. We are building something special.”

– Ricky Spiro, CEO, Hilb Group



Build relationships
Be transparent
Do what you say you will do


Communicate often
Be responsive
Be respectful of others
Embrace diversity


Be honest
Be accountable
Do the right thing


Love what you do
Show empathy for others
Have fun


At Hilb Group, we believe growth happens when you support and invest in one another. Associates have the opportunity to learn new skills and expand their networks – and are encouraged to do so through unique, comprehensive sales training and development opportunities.


When you join Hilb Group, you will advance your business knowledge, build professional skills, and gain meaningful work experience. Opportunities are available in each of these areas:

Finance & Accounting

Provide valuable financial solutions, mitigate business risks, enhance transparency, and identify business opportunities while ensuring we maintain a stable bottom line.

Human Resources

Deliver innovative human resource programs and strategies that support organizational growth, recruit and onboard top talent and acquired associates, and provide excellent compensation and benefit options to our associates.

Information Technology

Use strategic thinking and technology to find solutions that drive business initiatives and improve the user experience.


Promote our specialties and expertise, increase brand awareness, provide corporate, regional, and client communication and marketing efforts, and strengthen our positioning as a premier broker.

Mergers & Acquisitions

Work with the M&A team to grow our company organically through the acquisition of solid, established agencies that fit our corporate growth strategy.

Sales & Account Management

Learn new skills and expand your networks. New to the industry producers have the option to choose between two training paths: Property & Casualty or Employee Benefits and receive cutting edge sales training, in class development, and mentorship with our industry experts.


Richard G. Spiro

Chief Executive Officer

Ricky Spiro brings over 30 years of experience in the insurance and financial services sectors to the Hilb Group. From 2008 to 2016, he was Executive Vice President and Chief Financial Officer of The Chubb Corporation (Chubb), which was one of the world’s largest publicly traded property and casualty insurers. Before joining Chubb, Ricky was an investment banker specializing in advising the insurance industry on mergers and acquisitions, initial public offerings and equity and debt financings. Ricky was a Managing Director in the financial institutions investment banking group at Citigroup Global Markets Inc. (Citigroup) where he worked from 1999 to 2008. He held a variety of positions in Citigroup’s financial institutions group, including Head of North America and Head of Insurance Investment Banking. He began his investment banking career at The First Boston Corporation in 1986 where he was a Managing Director in the financial institutions group. He graduated from Princeton University with an A.B. degree in Economics. Ricky was also a member of the Board of Overseers of the School of Risk Management at St John’s University.

Richard G. Spiro

Chief Executive Officer

(804) 414-6509

R. Judson Elliott, Jr.

EVP – Mergers & Acquisitions

Jud Elliott was one of the founding members of the Hilb Group leadership team in 2009. Jud has over 30 years of industry experience, primarily in the employee benefits space. He began his career in 1983 as a group sales representative with The Travelers. He subsequently held senior leadership roles on both the insurance carrier side and the brokerage side of the industry, including Vice President, Major Accounts for BCBS of Georgia and South Region Head of Employee Benefits for Marsh. Jud is a graduate of the University of Georgia, where he earned a BA degree as well as a MBA from the Terry College of Business.

R. Judson Elliott, Jr.

EVP, Mergers & Acquisitions

(804) 414-6506

Ryan Havermann

SVP – Mergers & Acquisitions

Ryan Havermann is the Vice President of Mergers & Acquisitions for the Hilb Group. He is responsible for sourcing and executing agency acquisitions and facilitating integration work streams. Prior to joining the Hilb Group, Ryan worked for Harris Williams & Co., an international investment bank, providing M&A advisory services to clients in a variety of industries. Ryan began his career as a management consultant in Washington D.C. focused on strategy and business process improvement advisory services. Ryan earned his MBA from the University of Virginia, Darden School of Business, and his BBA in Finance from the University of Georgia.

Ryan Havermann

SVP, Mergers & Acquisitions

(804) 414-6508

Liam Duffy

Associate – Mergers & Acquisitions

Liam Duffy is an Associate on the Mergers & Acquisitions team at the Hilb Group. Liam is responsible for sourcing and executing agency acquisitions, acquisition due diligence, legal document review, and facilitating post-deal integration. Prior to joining the Hilb Group, Liam worked in M&A at Harris Williams, an international investment bank headquartered in Richmond, Virginia. Liam earned his MBA from the University of Virginia, Darden School of Business and his Bachelor of Arts also from the University of Virginia.

Liam Duffy

VP, Mergers & Acquisitions

(804) 381-4362