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Who is Robert O'Connor?  The purpose and hope of this section is to give you some greater insight and understanding into who Robert O'Connor is, not only Professionally but Personally as well.

Executive Summary

  • Robert was born in Stirling Scotland and grew up in the seaport of Liverpool.

  • He has had a diversified career touching on various vocations.

  • He was educated in a seminary boarding school in England, were he studied for the priesthood.

  • Destiny did not call for that perceived vocation.

  • His first major calling was to go to sea.

  • For 3 years he sailed on The Empress of England and was rapidly promoted to Fist class sommelier and purser’s writer.

  • In 1965 Robert emigrated to Canada.

  • An eventful evening had him enter the insurance business.

  • Rising from being a successful agent, Robert was promoted to management in the sale and marketing of insurance.

  • A few years later he was selected as Director of Training of sales and marketing managers for Canada. Travelling the breadth and width of Canada.

  • In the mid 70’s Robert grew restless; he missed the conducting the art and science of one-to-one selling.

  • He accepted a position with a major multi-faceted corporation as their President of insurance operations.

  • The corporation grew with his expertise, and bought 12 insurance brokerage firms, all negotiations done directly by Robert.

  • After a half dozen years Robert found he needed greater challenges and formed his own Mergers and Acquisitions (M&A) corporation as the advisor to the industry.

  • For going on 4 decades, he harnessed the trust of brokerage owners and sold more insurance brokerage firms than anyone in Canada!

  • He has also attended the Supreme Court of B C many times, as an expert witness on insurance brokerage valuations.

  • He is now semi-retired, accepting selective assignments that would benefit both he and a prospective client. Mainly in the sale of insurance brokerages, but also valuations for any reason.

Professional & Consulting Services

Insurance professional with proven successful experience in sales and marketing, valuation, mergers and acquisitions, training and education, consulting and general management.

Skilled Master of Ceremonies and speaker on a broad range of topics.

 Consulting Services Offered to the Insurance sector:


•           Operations optimization.

•           Analysis of the income and expense statements to maximise profit.

•           Sales training and sales course development.

•           Training sales managers in the art and science of closing the sale.

•           Strategic planning.

•           Developing marketing strategies and sales plans.

•           Company valuations.

•           Merger and acquisition negotiations.

•           Agency start-up support and established agency needs analysis.

•           Coaching and motivation.


Other Services Offered

•           Master of Ceremonies for events or meetings.

•           Speaking assignments. Skilled at speaking on a wide variety of topics.

References & Insights Assessment

The Insights assessment is highly accurate for you Robert. Specific phrases that resonated with me are as follows:

  • Structured and organized.

  • Never ending search for self-knowledge and self-identity.

  • Neat and orderly.

  • Goes to great lengths to fulfil responsibilities and obligations.

  • Tends toward perfectionism.

  • May dig his heels in to defend something he believes in.

  • Cares deeply.

  • Is very loyal.

  • Tends to take people and situations at face value.

  • Concerned with what is right.

It is emphasized that the above points are only those that most impressed me with the report’s accuracy and in no way is intended to lessen the validity of the entire report.


Personal Perspectives

Based on my interaction with Robert that started in 1980.  Here are some positive perspectives that I have:

  • Extremely focused on subjects of interest which are pursued with intensity and detail.

  • Superior photographer.

  • Outstanding communicator both orally and verbally.

  • Honest and trustworthy.

  • Generous with time and money.

  • Compassionate and caring.

  • Dedicated to his family.

  • Kind and does not expect reciprocity from those on whom he lavashes his attention.

  • Has presence and is a natural leader.

  • Conservative.

  • Looks for the good in people and gives them the benefit of the doubt.

In summary Robert has enriched my life and if there were more Robert O’Connor’s in the world it would be a far better place.



  • Born in Stirling Scotland, Baptized a Roman Catholic in Glasgow 

  • Has received 5 of the 7 Sacraments

  • Dedicated to his faith

  • His studies have led him to a deeper understanding of his faith

  • Grace, the soul’s heart, the soul, and eternity, Robert has studied with great intensity 

  • Robert Is looking forward to eternal life 



  • Robert is a lover of spiritual wisdom

  • His belief in spiritual alchemy holds great interest

  • He salivates, over all of philosophy’s great quotes

  • The hyperbole and euphemisms of Jesus capture his imagination

  • Good quotes crystallize his thinking

  •  Robert can easily separate the wheat from the chaff.



  • Robert has been a Sommelier 

  • An insurance broker

  • A sales and marketing manager

  • An executive of a multi branch-insurance network

  • The director of training for one of Canada’s foremost risk takers

  • Robert has represented more insurance brokers than anyone, in the sale or purchase of insurance brokerages, and valuations.

Tony Watts, October 23, 2022

Psychology Counsellor


Robert, you made a very large impact on the industry in your 40 plus years. You were a tremendous advocate for stronger valuations and as a result there was better liquidity and higher prices for owners who otherwise might have hung on and settled for mediocrity in their business as long as dividends and income could be taken.


Your actions allowed the bold souls (a few at first, then many) to invest and invigorate the broker channel.


All the Best,



Senator Scott Tannas

Former President/CEO and founder of Western Financial Group




Robert is like a father and grandfather and spiritual consigliere and business confident to me and I hold him in very high regard.


So needless to say, if you’re a friend of his, then you are a friend of mine.

Tom Siracusa

President & Managing Partner

iCare Insurance


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