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Paul Crossdale

benefitsConnect is turning a 170-year-old Insurance industry inside out. Our story, people want simple, flexible, and easy information to understand in one place. We deliver corporate benefits, savings, and perks programs using app-based technology. The platform is based on API connection (real-time), which integrates with an Insurance Company. Our solution enables a company to deliver a customized experience which includes an employee’s profile, benefits summary and booklet, sick day/vacation requests, view your savings plan, peruse your in-house library and more. benefitsConnect keeps you up-to-date and informed. Forget the Insurance company’s complicated lingo, terms and long process to implement plans, up to three to four weeks. Welcome to benefitsConnect, understandable language, everything in one app, and putting your plan in place in a one-day solution. Our communication banner enables companies to push communication to their employees in the areas of mental health, wellness, perks, and so much more. We keep you connected.

Tell us about yourself?

My parents are Jamaican and moved to England, where I was born, before coming to Canada. I love everything that being Canadian represents – a humble, strong frame of mind, being patriotic, the maple leaf, hockey, and bacon. In high school, I was pushed by an English teacher to not sit in the back of the class and give more. She was right, of course. After graduating from Western University with my English degree, I interviewed with London Life in their Employee Benefits Sales & Service Division on the advice of my roommate. After six to seven interviews, I think the profession picked me as much as I picked it. There’s an old saying, “You’re the first one, you’re the only one, and you’re everyone.” Being the first black minority in an older established division comes with challenges, but everyone was extremely supportive. Great West Life purchased my former employer, and I was given an opportunity to become Director of Eastern Canada, Selectpac. The only caveat was my family and I had to move to Winnipeg, Manitoba. After too many planes, staffing issues, budget meetings, and being away from the family, I decided to open my own firm in Toronto. After 22 years, benefitsConnect is leading the way with technology-based communication.

If you could go back in time a year or two, what piece of advice would you give yourself?

Everyone has an opinion…believe in yourself, bring your “hustle” to work daily, and surround yourself with a smart/dedicated team.

What problem does your business solve?

Insurance companies are built on old legacy systems, complicated language, and a lack of employee understanding. It takes three to four weeks to set up a small business employee benefits program. There is no creativity in products. You can’t find all the information you want in one place. Trying to work with numerous people through the underwriting process doesn’t speed things up. It slows things down. The lack of API connectivity is embarrassing.

What is the inspiration behind your business?

Using technology enhances communication with employees, whether they are in the office, working a hybrid schedule, or working from home. We understand that today’s employees consume information differently and want access to traditional and nontraditional products in one app. If an employer invests money in an employee benefit plan for his employees, shouldn’t that plan be set up overnight?

What is your magic sauce?

Others have tried to implement these “human capital” platforms. They were tech startups getting into Insurance. The secret sauce is we are Insurance people who now understand tech.

What is the plan for the next 5 years? What do you want to achieve?

Today, we love where we are at. We are growing quickly. Could we grow even faster? Yes. I’ve explained it as crawling, walking, jogging, and then sprinting. benefitsConnect is currently jogging. The next five years will see us develop a business model (pilot in process now) which will make our technology available to every advisor in Canada. Then let the sprinting begin!

What is the biggest challenge you’ve faced so far?

Getting the word out! The benefitsConnect OS is fast, easy, and works in real-time. You don’t need to use multiple systems that don’t talk to one another or let information slip through the cracks. Host everything in the benefitsConnect OS using API technology.

How can people get involved?

C-Suite, HR Managers, Insurance Companies or Advisors can reach to us at