Sentry news and thought leadership

Sentry earns national award from TIME as one of America’s Best Mid-Size Companies, reflecting the values and dedication of associates.

AM Best cites Sentry’s capital and balance sheet strength, the diversity of its business lines, and a track record of stable operating performance as reasons for the company’s strong financial rating.

Sentry earns national recognition from Forbes as one of America’s Best Employers for New Grads in 2025—see how we’re supporting early career talent.

Tournament officials, alongside representatives from Sentry, announced over $747,000 gifted to local nonprofits to support key initiatives across West Maui.

A Sentry survey finds 82% of large business leaders are experiencing higher stress levels this year, driven by supply chain issues and ongoing economic uncertainty.

The 2025 Sentry Scholars recipients display a wide range of interests. To date, the Sentry Foundation has provided $118,500 to Maui students through the program.

Pete Anhalt, currently president of Sentry’s Dairyland^® brand, will lead The General^® following Sentry’s acquisition of the non-standard auto brand.

Sentry earns spot on Newsweek’s list of top workplaces for women.

Forbes once again recognizes Sentry as a workplace leader based on an independent survey of 217,000 U.S. workers.

The General’s new A+ (Superior) rating reflects Sentry’s balance sheet strength, operating performance, and favorable business profile.

The Sentry Pickleball Complex in Plover—partially funded by Sentry's $500K donation—will offer 12 courts for players of all ages and abilities this summer.

New survey data of 1,000 U.S. business owners and C-suite leaders indicates executives are more stressed in 2025 as businesses forecast external risks.

Sentry finalized its acquisition of The General^® from American Family Insurance, enhancing its leadership in non-standard auto insurance with expanded capabilities.

With an additional $1M donation to Maui United Way, Sentry continues its commitment to youth mental health services after the wildfires.

Sentry Insurance employees come together during their annual United Way campaign, raising $1.7 million to support their communities.

Sentry moved up one spot on the 2024 Wisconsin 75. Its success reflects a long-term growth strategy, forecast to continue in 2025.

Sentry Insurance announces acquisition of The General^® from American Family Insurance, expanding its presence in the non-standard auto market.

In its annual survey, Forbes recognizes Sentry among Wisconsin’s best employers for the eighth consecutive year.

The Sentry Insurance Foundation is donating $150K to the Pu’u Kukui Watershed Preserve to support the organization’s critical work as the primary water source for the west side of the island.

New program will offer primary and excess E&O coverage for insurance, real estate, and miscellaneous licensed professionals.

AM Best points to a “favorable” business profile as a reason for the superior rating.

The Sentry, alongside representatives from Sentry Insurance, announced that more than a dozen Maui non-profit organizations benefitted from the 2024 event, which generated $735,694 in charitable funds.

Mutual insurer’s expansion into marine cargo will offer admitted and non-admitted cargo capacity to Falvey’s broker partners.

Exciting recognition: Sentry named by Newsweek as a top workplace for women. Learn about our commitment to supporting and empowering our employees.

The 2024 Sentry Scholars recipients display a wide range of interests. To date, the Sentry Foundation has provided $93,000 to Maui students through the program.

Headquartered in Stevens Point, Wisconsin, Sentry joins a select group of just 400 companies nationwide that made the list.

Team recognized for trucking expertise, tailored services, and customer satisfaction.

The Malama Keiki Initiative aims to support Lahaina and West Maui children in healing from the devastating wildfires that took place in August 2023.

Sentry Insurance employees come together during their annual United Way campaign, raising $1.668 million to support 17 communities.

Plano-based team offers Texas businesses greater access to insurance and risk management services.

Sentry’s commitment included a surprise visit and donation to four Maui non-profits. The company will also recognize The Sentry event qualifiers by making a $2,000 donation in each player’s honor for the 2024 event.

The Technology Innovation Initiative is focused on accelerating K–12 learning through innovative uses of technology. Four Stevens Point school partners were awarded funds as part of the program.

Sentry credits technology innovation, market expansion, and talent investment for placement on Deloitte’s Wisconsin 75 list— a ranking of the 75 largest private companies in Wisconsin.

Sentry obtains ISO 27001 certification—the gold standard—with its rigorous, structured approach to data management.

Sentry is donating $150K to Maui Food Bank and $228K to Maui United Way—a portion of these funds was raised by Sentry associates, retirees, and board members, then matched by the Sentry Foundation.

Advancing 13 spots from 2022, Forbes ranks Sentry among Wisconsin’s top 35% of employers.

Sentry establishes scholarship program to aid students, invest in El Paso’s future.

Recognizing the road to recovery will be long, Sentry is donating $275,000 to address immediate needs in the aftermath of Maui wildfires—and the Sentry Foundation will match employee donations.

AM Best points to a “favorable” business profile as a reason for the superior rating.

Tournament officials and Sentry representatives announced that more than a dozen Maui non-profits received funding from the 2023 Sentry Tournament of Champions.

Sentry signed a three-year renewal as a Featured Product provider of the American Trucking Associations (ATA).

Predictive tool to help identify early risks for chronic pain and psychosocial factors, promoting improved workers’ comp outcomes.

The reforms include elimination of one-way attorney fees and fee multipliers for all lines of insurance, modernization of Florida’s bad faith law, and protection of small businesses.

The reforms include elimination of one-way attorney fees and fee multipliers for all lines of insurance, modernization of Florida’s bad faith law, and protection of small businesses.

Optional telematics program offers premium discounts and more efficient claims processes for transportation customers practicing safe driving.

Sentry-led Connected Communities initiative brings together Maui and Stevens Point breweries for collaborative IPA: Hula Badger.

Denver-based team to offer regional businesses greater access to insurance and risk management services.

Sentry Foundation gift will help the university create a state-of-the-art facility to house its Sentry School of Business and Economics.

The Borderplex Region’s bilingual workforce and growing, diversified economy a draw for the mutual insurance group’s newest field office.

With a combination of in-person events, employee pledging, and a contribution from the Sentry Insurance Foundation, Sentry raised more than $1.6M for United Way.

Forbes names Sentry among its Best-in-State Employers. This is the sixth consecutive year Sentry has been named one of Wisconsin’s best employers.

The honor reflects the mutual insurer’s commitment to helping fill community gaps year-round on island, not just during the Sentry Tournament of Champions.

In the wake of Hurricane Ian, the Sentry Foundation pledged $25,000 to the Florida Disaster Fund and matched employee donations.

Trends in telematics, social inflation, and diversity in trucking highlighted at 20th Sentry Agency Transportation Conference.

The Women in Trucking Foundation is dedicated to advancing and empowering women in the trucking industry through education.

Sentry credits technology investments, growth, as reasons for its continued business success and climb to 650 on the Fortune 1000.

Extending through 2035 continues the insurer’s strong support of the Maui community and the game of golf.

Former VP of Underwriting to lead Sentry’s excess and surplus (E&S)/specialty lines division.

2022 charitable donations generated surpassed last year’s record by more than $100,000, and brought the total raised since 1999 to more than $8 million.

With 40 years of experience in golf course management, Sentry will begin offering commercial insurance to golf courses.

The upscale hotel will serve destination golfers, visitors to the central Wisconsin community, and the mutual insurance group’s business clientele.

Forbes names Sentry one of America’s Best Midsize Employers in 2022 based on survey of 60,000 workers.

By building upon shared values and exchanging mutually beneficial ideas, the initiative strengthens growing connections between Maui and Stevens Point, Wisconsin.

Scholarship program provides $15,500 in support of Maui public high school graduates staying on the Hawaiian islands for college.

Sentry donates $100K to Maui United Way to provide meals to 1,500 children during their winter break from school.

This proactive step will help cultivate a safe environment for the mutual insurance group’s employees and guests at its offices across the country.

Sentry Foundation donates $1.5 million to honor Cherry Starr and her late husband, legendary Packers’ quarterback Bart Starr, co-founders of Rawhide.

Through this partnership, Sentry will help expand golf-related programs that help kids and teens build character.

Based on a survey of 80,000 U.S. employees, Forbes named the central Wisconsin mutual insurance group to its third-annual ranking of America’s best employers by state.

Risk assessment tool aimed at helping dealerships identify, measure, and reduce risks.

Mutual insurance group moves up 12 spots on 2021 list based on total revenues.

Sentry partnered with the Wisconsin Professional Golfers’ Association of America to become title sponsor of the Wisconsin State Women’s Open golf championship.

Sentry charitable impact tops $1 million as the Tournament of Champions raises a record amount for nonprofits since the event moved to Maui in 1999.

Sentry becomes USGA’s sixth corporate partner. The Wisconsin-based mutual insurance company aims to broaden golf’s reach and advance the game in innovative ways.

The USGA’s 43rd U.S. Senior Open Championship will be held at SentryWorld in Stevens Point, Wisconsin from June 29–July 2, 2023.

Sentry Insurance Foundation donates $250,000 to the Maui Food Bank to help island residents and businesses during the pandemic.

Sentry Insurance Foundation scholarship program supports students staying on the Hawaiian islands for college.

The conversion, effective January 1, 2021, expands the company’s mutual structure and improves its ability to offer more products and services to customers.

Sentry among 75 employers in Wisconsin named to the second-annual list.

Community, cultures of Stevens Point, Wis., and Maui will be on display at the Sentry Tournament of Champions on face masks designed by students.

The Wisconsin 75™ Distinguished Performer award the result of Sentry’s ongoing commitment to building better communities.

Chad Bates brings Wisconsin values and experience running luxury properties to the new boutique hotel at SentryWorld in Stevens Point, slated to open in 2021.

Employees increased their personal pledges and conducted a spirited, two-week virtual campaign to address rising need in their communities.

The Sentry Insurance Foundation’s $15 million in donations to boost technology in Stevens Point schools helped students transition smoothly to e-learning.

More than a dozen charities benefited from the 2020 event, which surpassed $7M raised for community nonprofits since the Tournament of Champions moved to Maui in 1999.

Sentry Insurance Foundation makes community-focused donations aimed at making a direct impact at the local level where Sentry associated live and work.

Community-focused donation to the United Way of Portage County aimed at making a direct impact at the local level.

Community-focused donation to Maui United Way aimed at making a direct impact on the island community.

The International Association of Golf Tour Operators (IAGTO) names SentryWorld a quality assured golf course for the 2020 season.

Being title sponsor through 2030 enables mutual insurer to continue to build relationships with customers while positively impacting the Maui community.

Sentry donates $200,000 to the Arizona Leadership Foundation to fund scholarships to private schools for financially disadvantaged students.

The Golf Course Owners of Wisconsin has named SentryWorld—located here in Stevens Point—its 2019 Destination Golf Course of the Year.

Establishing the Sentry Deanship will boost training programs and help secure access to quality healthcare for families in central Wisconsin.

With a Sentry Insurance Foundation donation, the Stevens Point Curling Club says it can now construct a state-of-the-art curling center in 2020.

Backed by employees’ ingenuity and giving hearts, Sentry raised more than $1.5 million for United Way at its offices countrywide.

With a $125,000 donation from Sentry Insurance Foundation, the University of Wisconsin-Stevens Point will build a Green Circle Trail plaza in Schmeeckle Reserve.

New mutual holding company structure better positions insurer for growth while preserving mutual-based culture.

The foundation offered the donation after Luna, a beloved police dog who joined the force last year, died unexpectedly due to organ failure.

The on-course, upscale hotel in Stevens Point, Wisconsin, will serve the company’s business clientele, golfers, and visitors. It will open in spring of 2021.

More than a dozen nonprofits benefited from the 2019 PGA TOUR event. Sentry also established a scholarship program for Maui public high school students.

Sentry continues to climb the Fortune 1000 rankings, having moved up 114 slots since 2015.

Forbes names Sentry one of America’s Best Midsize Employers in 2022 based on survey of 60,000 workers.

Our enhanced analytics program improves our claims professionals’ ability to leverage predictive models and modern technology to manage workers’ compensation claims.

State-of-the-art facility will help mutual insurer attract and retain quality employees.

Sentry climbs the Fortune 1000 list, and Forbes includes Sentry among America’s Best Employers for Women and Best Midsized Employers.

Backed by employees’ energy and enthusiasm, Sentry raised more than $1.5 million for United Way at our offices countrywide.

SentryWorld is proud to host the 71st U.S. Girls’ Junior Championship on July 22–27, 2019. It’s the first course in Wisconsin to host this prestigious event.

The gift recognizes officers’ response to a nearby workplace shooting. It will help the department develop a K-9 team.

New Stevens Point program is based on Sentry’s highly successful Madison internet technology co-operative program, focused on training IT-related college students.

Sentry gives UW-Stevens Point $4 million donation to create a new major in data analytics, and endow two faculty positions.

Sentry grows Regional business by opening a Pacific Region office in Irvine.