Through all the change and growth Henderson Insurance has remained true to the Core Values that the company was built upon.  The company feels the pinnacle statement within the values is: We put the client in the middle of everything we do.

Dave Reidy

President and CEO, Henderson Insurance Inc.


While the Henderson name has been part of the Saskatchewan insurance circles since the early 1900’s it wasn’t until 1965 that it began its journey to becoming one of Saskatchewan’s premier insurance brokerages.

In 1965, Frank Reidy purchased the small local agency and began to build.  Frank had a passion for business, insurance, and helping people.  These passions were the impetus for Henderson Insurance’s current unique approach to the business.  Frank saw a need for a brokerage to offer advice around the management of risk.  Together with his family, staff, partners and the support of insurance companies he grew and adapted the business through the 1960’s, 1970’s and 1980’s.  Throughout this time the company had branches in Regina, Calgary, Winnipeg, Saskatoon, and its home office in Moose Jaw.

In the 1980’s, the second generation of the Reidy family began to join the firm.  Greg Reidy joined Henderson Insurance in 1984 after receiving a Bachelor of Science (Mathematics) from the University of Regina.  His forward thinking and innovation in the areas of technology and risk over the next several years moved the company forward and set the table for the next big company change.  Greg assumed the role of President and CEO in 1995.

In 1990, Rick Smith joined Henderson Insurance after a successful career in sales and sales management with a direct writing insurance company.  Rick brought a much different and needed approach to sales.

Later in the 1990’s, Dennis and David Reidy joined the company after careers in teaching and coaching.  These two brought skill sets around program and team building, culture building, planning, accountability and leadership.  These two additions lead to the perpetuation of the company from Frank to Greg, Dennis, Rick and David in 1997.  This ownership structure remains intact today.

The next 7 years was highlighted by great growth.  The company began to be exposed to a variety of new industry segments such as Farm Equipment Dealers, Non-Profits, Ski Hills, Auto Dealers and Manufacturers.  However, they stayed true to their past and continued to grow in the Commercial Construction industry due to their expertise in the handling of Contract Surety Bonding.

In September of 2004, the company went through another transition when David Reidy assumed the role of President and CEO.  Greg stepped down to assume the role of Chief Operating Officer of the family held Henderson Hail Agencies. This provided Dennis (CEO of Henderson Hail) needed support to grow that venture.

During the following five years the company again had tremendous growth.  This growth was not only in revenue numbers but also in the amount of staff, the diverse backgrounds and abilities of the staff, and the creation of a dynamic leadership team.  Further, the company acquired Jordon Ewart Insurance in Regina giving the company a much sought after Regina location.

CEO David Reidy states “Businesses in Moose Jaw gave Frank an opportunity in the mid-1960’s when his company was very small.  They gave him the opportunity because they trusted him.  It is critical that we all recognize this, even though we are now exponentially larger and do business throughout many areas of Canada, that our clients give us that same opportunity every day.  It is something that we must not ever forget or take for granted.”

Henderson Insurance is poised to continue growing, and innovating into the future.