Insurance Squared has 20+ years honing our online marketing and sales experience, centered on the insurance industry. Well before the insurance industry thought of going online, we started in 1999-2000 with an e-commerce store (we were one of the first hundreds of companies to take credit cards online in Canada in any industry). Over the decades, we have continually refined our skillset using technology and online marketing to find and convert high quality insurance consumers. Here’s a sampling of some of the websites we’ve worked on over the years.

Currently in pre-production. Using all of SEO, SEM and social media, we’ll be driving consumers to this home and auto website with an emphasis on high premium, low loss ratio clients.

Phase two will be implementation of a life insurance department. Past experience indicates that average sales to the client block will be $750 average premium, with a near 15% closing rate.

Currently in pre-production. This website will be targetting financially astute consumers seeking information by providing extensive and indepth coverage of individual financial topics, well beyond the realm of a blog post.

Monetization will initially be through advertising, then later through lead generation for

Canada’s leader and trailblazer in online life insurance. Our top quality SEO brought front page google rankings consistently for over a decade – something few if any SEO agencies can claim. Heavily customized tech was used to expedite both sales and administration. Along the way we assisted numerous life insurance companies with understanding the compliance and field underwriting associated with non-face to face sales, including developing their agent guidelines. As a result, we were the first non-face to face broker for some of the largest insurers in Canada.

The business, website, and client block were acquired by other insurance agencies in 2019.

Partnering with an American actuary, we initiated Canadian and American conferences for actuaries. While most actuarial conferences focus on technical skills, GoActuary filled the need for career growth and networking in the industry.

Launched in early 2020, the first conference was booked at the University of Waterloo with a second conference for New York planned for September. Then Covid hit…

Bringing together some of the best independent financial bloggers created this popular beginners guide for Canadians. Edited by Dan Bortolotti (Canadian Couch Potato) and included such online personalities as Million Dollar Journey, Krystal Yee, and Canadian Capitalist (and Insurance Squared’s Glenn Cooke) Self published, a thousand copies were sold – an outstanding number for a self published book in Canada. Originally intended as a media promotion tool, it’s being repurposed to bring in traffic to Read the reviews on Amazon.

An online advertising agency focused on the Canadian financial industry. We connected 50 of the top independent financial blogs and resold their inventory directly to the financial institutions.

Our publishers included industry names as Preet Banerjee, Gail Vaz-Oxlade, Dan Bortolotti, and Million Dollar Journey.

Financial clients included Empire Life, BMO Investorline, and a variety of other banks and financial institutions.

The internet’s largest actuarial community for 20 years. Co-founded with an actuary, we built the ‘AO‘ ( into the huge site that it is today, with thousands of actuaries online at any time.

When we founded the site, technology and hardware made a difference in websites. We leveraged this as an advantage over our competitors.

Acquired by D.W. Simpson Actuarial Recruiters in 2004, the AO continues as a dominant online actuarial community even today, unchanged from when it was acquired.


Founded in 2000, RapidAct was Canada’s first online actuarial bookstore and one of the first hundreds of Canadian businesses to accept credit card transactions online. In a market dominated by large American retailers, we overtook the Canadian market in our first year.

By our second year we had expanded into the lucrative US market. Within a month of announcing our international presence we were acquired by an American actuarial bookstore.