The Insurance Library 2024 Insurance Professional of the Year Award Will Be Presented to Royce Cross, Chairman of Cross Insurance, on October 4, 2024

Royce Cross, Chairman of Cross Insurance

Royce Cross, Chairman of Cross Insurance, will receive the Insurance Library’s 2024 Insurance Professional of the Year Award. Sonya Ross, the Library’s President and Board Chair, will present the award at a luncheon gala on Friday, October 4, at the InterContinental Boston. See below for ways to support this event.

About Royce Cross

Mr. Cross began his career at Cross Insurance in 1970, manually typing policies under the guidance of his father, Woodrow Cross, founder of the agency. Royce took on greater responsibilities over the years and was named President of the company in 1983, later taking on the role of Chairman.

Over more than five decades, Mr. Cross has helped shape and steer his family’s namesake agency into becoming not just an insurance staple of Bangor, Maine, but one of the largest insurance providers in New England. As the result of more than 170 mergers and acquisitions, Cross Insurance now has more than 1,100 employees in more than 50 offices in Maine, Massachusetts, New Hampshire, Vermont, Rhode Island, Connecticut, New York, and Florida.

“This award is very much about my father and his contribution to the business,” remarked Jonathan Cross, CEO of Cross Insurance. “At the heart of this legendary adventure is a man that loves his business, loves this industry, and is at his best when he’s doing a deal. For several years now I have challenged others in the industry to find me someone else that loves this business more than my father, and so far nobody has yet to find one.”

Cross Insurance provides an extensive range of insurance and financial products, including personal and commercial lines insurance, employee benefits, and surety bonds. Its

customers range from individuals and sole proprietors to large private and publicly traded companies. Among its more well-known clients are Kraft Sports and Entertainment–includig the New England Patriots and the New England Revolution–and the Boston Red Sox.

History of the IPYA

The Insurance Professional of the Year Award was first made possible by the establishment in 2001 of the Richard B. Simches Fund. Mr. Simches, who founded Safety Insurance Company, believed that it was important to recognize outstanding individuals in the insurance industry. The award was created by the Library’s Board of Trustees in the tradition of an award bestowed annually from the 1950s through 1996 by the Boston Board of Fire Underwriters.

Since 2002, when the Library first presented this award, a broad cross section of members of the insurance, financial security, risk management, and legal communities has gathered to recognize an individual who demonstrates outstanding leadership and exemplifies qualities that foster commitment to, understanding of, and respect for the insurance industry.

OCTOBER 4, 2024, GALA

The gala will start at 10:30 a.m. with an extended time for socializing, networking, and bidding on an array of items at the always-popular Silent Auction, which benefits the Library’s programs and operations. A cash bar will be open. The luncheon will start at Noon in the ballroom, followed by the award ceremony.

Purchase Sponsorships
Visit this page to learn about sponsorship opportunities and to purchase a sponsorship. Sponsors will receive an email with an invoice, information on payment (we prefer check or ACH), providing their logos, providing names of guests, and how to pre-order bottles of wine. All sponsors will receive a tax receipt after the event, which will state the tax deductible portion of the purchase.

Purchase Individual Seats
Visit this page to purchase individual seats. All purchasers of individual seats will receive a tax receipt after the event, which will state the tax deductible portion of the purchase.

Sign the Congratulatory Letter in The Standard
Visit this page to learn how an organization or individual not purchasing a sponsorship may have their logo or name included in the congratulatory letter that will be published in The Standard.

Donate to the Library in Honor of Royce Cross
Visit this page to learn how organizations or individuals, including those who cannot attend the gala, wishing to acknowledge Royce Cross for his receipt of the award may donate to the Library in his honor. Those donating at least $500 will have their logos or names included in the congratulatory letter published in The Standard and will be acknowledged in the event program.

Donate Silent Auction Items
If you or your organization wish to donate items to the Silent Auction, please contact Sarah Hart, the Library’s Education and Event Coordinator, at events@insurancelibrary.org. To see a list of the items already donated, visit this page.

Click Here for a Brief History of the Insurance Professional of the Year Award

Past Winners of Insurance Professional of the Year Award