Recognizable by the Revolutionary War patriot sentry logo the company has used for decades, Sentry Life Insurance itself has been around for more than a century since it was started in 1904. Operating as a mutual insurance company based out of Wisconsin, Sentry Life was another insurance consortium started by a number of hardware associations to give a group insurance protection to the association members. Over time, the company has evolved to now being a full-fledged insurance business corporation offering the full portfolio of consumer risk protection in property-casualty, auto insurance, health coverage, group health, and life insurance to individuals and business clients.

Sentry companies and subsidiaries include the following:

Sentry Insurance a Mutual Company
Sentry Life Insurance Company
Sentry Life Insurance Company of New York
Sentry Equity Services, Inc.
Sentry Select Insurance Company
Sentry Casualty Company
Sentry Lloyds of Texas
Dairyland Insurance Company
Dairyland County Mutual Insurance Company of Texas
Dairyland Cycle Insurance
Middlesex Insurance Company
Patriot General Insurance Company
Parker Services, L.L.C.
Parker Centennial Assurance Company
Peak Property and Casualty Insurance Corp.
Viking County Mutual Insurance Company
Viking Insurance Company of Wisconsin

As of 2012 the company boasted over $11 billion in assets, rounded, and a surplus in policy holder funds of almost $3.4 billion, providing the company plenty of buffer for losses and claims. These funds represent the protected interests of over 1 million policyholders total. The Sentry Insurance Group itself is made of a 17 different companies and subsidiaries, ranging from strict auto insurance to property-focused services to life insurance. All of the given subsidiaries feed into the strength and capacity of the overall company through their specialties and line of insurance products.