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How Canadian advisors can establish a path to success by generating new opportunities in the health benefits field 

“I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance.” Steve Jobs

Starting a new career as a self-employed individual in today’s climate can be a daunting task. Whether you were laid off during the pandemic or you want to own your own firm, working on commission can be frightening but it doesn’t have to be. 

Hopefully, you’ve made the decision after crafting a well-thought-out plan, but, more importantly, after deciding WHY you are taking the leap. Is it flexibility? An opportunity to generate more income? Maybe you enjoy the idea of being your own boss. All of these are relevant however I think the importance lies in finding the right balance of the following; What are your needs? What are you good at? What can you be paid for? and what do you love? This concept is known as “Ikigai” and its origins are thought to be native to Okinawa Japan. Coincidentally enough the Okinawan language (uchinaaguchi) does not have a word for retirement. This approach to life could also be one of many reasons why Okinawan’s have historically per capita the most centenarians in the world in what is known as a blue zone. However recently there has been an increase in influence from the Western world (fast food, less exercise, stress from modern living). This has created a loss of a feeling of Ikigai in the younger generations contributing to the drop in Okinawa’s life expectancy.

Blue zone – Wikipedia

While starting on your path typical questions that arise are where will I get clients? How will I approach decision-makers? What if things don’t work out? Am I ready for this? This is completely normal. 

Having worked more than 15 years in the financial services industry as both an advisor for business owners and decision-makers and as an account executive working with thousands of advisors, I have come across re-occurring patterns in generating new business. Below is a further explanation of these themes in greater detail, followed by specific success stories.


Why am I doing this? Most advisors have a specific purpose which is often the catalyst that drives their effort. Just as important is their ability to set themselves apart and stand out. A former colleague who now runs his own practise with another former co-worker once asked me this question while I was making cold calls in my nascent career “why should a prospect listen to you and not the other advisors who called them today?” It had a profound effect on the approach I took with how I conducted business and helped me focus on finding a way to stand out. 

The 4 common differentiators I found with most advisors are the following; Work experience/knowledge, Network, Industry Designations, Personality/Approach to work. Each advisor combines their own unique mix. I have met advisors with plenty of credentials but lack character and/or business acumen. Others have plenty of work experience with great work ethic but lack the network to prospect. Some hold prestigious designations but don’t have the industry knowledge to match. What I have found was that what you lack in one area is important to make up in another. Having all 4 is the ideal recipe for success.

There is a famous and often over-used saying, “Hard work beats talent when talent isn’t working hard.” As cliché as it is, it’s extremely relevant in the group benefit’s landscape which can often be described as a number’s game.


In Ontario alone there are 444, 702 small business (1-99 employees). LinkedIn and company websites are a great place to find the potential decision makers. Working the path of least resistance like your social network is often a starting point for most fledgling advisors. Many advisors work with the following; family, friends, former colleagues, Facebook, Instagram, recreational leagues, services or professionals you use like your dentist or physiotherapist.

Key Small Business Statistics 2023 (

You may have work experience or education in another industry which would make it easier to break the ice and strike up a conversation. I’ve worked with advisors who focused on construction or fitness because of their prior work experience for example. Some advisors focus on a specific geographic area, size of company, or market (golf courses in Halton region or start-up tech companies under 100 lives).

Each region and municipality in Ontario often has an excel spreadsheet, online database or pdf that can be downloaded or purchased for free.

Other common places to find leads or business are; referrals from existing clients or people you know, a referral plan with business lawyers, accountants, bankers, lead generation companies, classified ads, leaving business cards and/or marketing documents in high traffic areas, attending events specific to your approach (new professionals like doctors, lawyers, engineers, Human Resources, start-up companies looking for investments, government funding for businesses) targeting franchises and asking for leads from your account executives at difference insurance companies.

Finally, there is the option of purchasing an advisor’s block or working in tandem with an advisor who specializes in other services (Property and Casualty or Life Insurance).


A well thought out value proposition unique to you is extremely important. Just as important and something that is often overlooked is not just your method but your tone of delivery. Will you be cold calling, emailing, messaging via social media or walking in person (yes, some people still do this). Will you focus on a plan service agreement such as better turnaround times, caps at renewal, access to enhanced services or products like a more robust EAP (Employee Assistance Plan), involve a TPA (Third Party Administrator) or the often overused reduced pricing. How forward will you be in pushing for a meeting? Will you at a minimum ask for the carrier and renewal date and ask to follow up at a better time?

Success Stories

Below are a few examples of actual sales advisors made based on some of the topics mentioned above.


After following up with the office manager of a large multinational company on numerous occasions checking in on the benefits plan, the advisor was eventually transferred to the CFO and eventual decision maker. After the advisor earnestly opened with, “You probably get these calls all the time,” the CFO responded with, “Actually I don’t, thank you very much for calling.” The advisor’s persistency eventually lead to winning a 200 life group.

Repairing Trust

The decision maker at this mid-sized company was disillusioned by their relationship with their past advisor after a large increase in rates followed the initial period of savings. The advisor decided to earn back their trust in increments by setting small goals such as calling back at a certain time and date, sending a newsletter with industry changes and following up with an email explaining certain products and services in greater detail. Over the course of a few years the advisor won the group back.

Perfect Storm & Timing

After running into an old friend from school and making small talk the advisor set up an initial meeting with the friend’s parents and owners of this local construction company. They eventually won the group by recommending plan design changes resulting in significant savings. Most importantly, the fact that there was no relationship with the advisor, poor service and rising costs helped them win this group.

Social network outside of work

Another advisor won a smaller group simply by having the conversation at a men’s league event with a family friend whom they did not know managed their own company. Luckily for them, their friend was unaware that they didn’t even have an advisor.

Franchise opportunity & and word of mouth

Having done such a good job with one business location’s benefits plan in this automotive company, this advisor eventually won numerous franchises which lead to a much more lucrative deal. Success by association is what worked in this instance after one business owner decided to contact the other franchise owners which helped them decide to move their business over to the new advisor and carrier. 


A close friend of mine and fellow advisor who specializes on the individual side was successful in winning many of client’s group business simply by disclosing his commission while the incumbent advisors were not.

Maximizing opportunity

Finally, after winning the benefits plan contract this advisor with the permission of the business owner would hold a session for employees where they would discuss individual insurance, RRSP’s, TFSA’s, Mortgages and other individual products.

There are plenty of different ways to generate new business. Each story is uniquely different given the approach, relationship and timing of the situation. Whether you are starting from scratch marketing yourself, purchasing a block, working with another specialist or have access to a prestigious social network, a few things remain the same. Purpose, niche, approach and effort.

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