CEO of Archway Insurance: 'Working with my family is the best part of the job'

CEO of Archway Insurance: 'Working with my family is the best part of the job' | Insurance Business

CEO of Archway Insurance:

Atlantic-based brokerage Archway Insurance burst into the limelight in 2017 by doubling in size through organic growth and focused M&A activity. Rapid growth inevitably partners with growing pains – but the brokerage is soldiering on by staying focused on its family roots.

Archway Insurance CEO Michael Stack has been in the insurance business since 1998. As a boy, he watched his father help people in the local community and dreamed of following in his footsteps. The family man has done just that.

Working alongside his parents, siblings and his wife, Stack has successfully steered Archway Insurance through a number of years of sustained growth. The brokerage’s consistent successes culminated in the Markel Award for Big Brokerage of the Year at the Insurance Business Canada Awards 2017.

In the meantime, the dad of two finds time to coach his son’s hockey team and make the most of the family moments that matter. Insurance Business caught up with Stack to learn more about his insurance journey.

How did you get started in the insurance industry?

Archway Insurance is a family business, which started as a typical small-town brokerage in rural Canada. I joined the business because my father was a previous owner. I remember going into the office as a young fella, sitting at my father’s desk and hoping I would be able to run the brokerage and help the community one day. At that point in time, we only had one office and we were a much smaller brokerage than we are today, but I still always dreamed of being part of the family business. I admired my father. He was my idol growing up and I always wanted to be like him.

Archway Insurance is a very family-orientated business. How does that work?

It can sometimes be a double-edged sword when you have multiple family members working in the same business. But the positives far outweigh any negatives. When you’re working with family, you’re working with a group of people who have the same set of values and the same goals. There’s complete trust within the family, which has really enabled us to work together and grow the business. At one point, I was working with both my parents, my brother, my sister and my wife. Everyone’s on the same page, so for us, it works.

What are the best parts of your job?

Aside from working with my family, the best part of the job is helping people. As insurers, we protect people and enable them to live their lives with peace of mind. Being in a position to help people is by far the best part of the job.

Our industry is ever changing. The insurance landscape is evolving rapidly and challenging how we do business. I find that disruption and evolution really exciting and enjoy finding ways to take Archway Insurance through those changes. Another thing I love about the job is seeing employees thrive. In 2017, Archway Insurance doubled in size, growing from 11 to 22 offices and from about 80 to 150 staff. It’s a huge pleasure seeing staff grow with Archway and move up in the ranks. 

What challenges have you faced in your role?

One of the things I described as the best part of the job – that changing insurance environment – is also one of the greatest challenges. In addition, HR always seems to be a challenge. There doesn’t seem to be an abundance of up-and-coming insurance professionals to take our brokerage (and others like us) to the next level. That said, we’re fortunate at Archway Insurance to have some wonderful staff and we’ve done well getting the right people in. So far, it’s a challenge we’ve been able to overcome.

As far as personal challenges go, maintaining a work/life balance as CEO of the company is tough, especially considering how busy we are at the moment due to our rapid growth. I have two young children, aged 12 and seven, so spending precious time with them and not letting work define everything about who I am is very important. 

What advice would you give to someone working their way up the insurance ladder?

Never be afraid to say yes. Be flexible and try to assist in any way possible, whether that’s helping with a project or considering a work transfer. Take every opportunity you can to grow and round out your skills.

Always remember that insurance is a people business. It’s just as much about who you know as what you know. We’re in sales and the brokerage business is about relationships and connecting with clients and co-workers. Come into work with a smile on your face and take the time to care about your co-workers and your clients.

If you weren’t working in insurance, what would you be doing?

I would love to be a hockey coach. I coach my son’s hockey team and it’s something that gives me great joy. Coaching is very similar to what I do here at Archway. It involves helping people and watching them grow.  

Do you have any other hobbies?

I really like volunteering, which is where the hockey coaching comes in. I also enjoy travelling and play a little bit of golf if I have time.


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  • 2018-03-15 10:41:07 PM
    I have known your mother and father most of my life and admire the foresight that they had in the insurance industry. It is reassuring to know that your family business will continue to stay strong and grow in the future under your knowledge and positive outlook. Continued success.
    Post a reply
  • Dick Audas 2018-03-17 2:52:21 AM
    Excellent article, well done Michael.
    Post a reply