Jeff Arnold is the founder of RIGHTSURE, one of the most awarded insurance firms in North America.  He is the author of five books with four of them holding the highly coveted spot of #1 Bestseller.

Jeff has been called a Thought Leader and Global Ambassador for the Insurance Industry. A title he maintains that most executives in insurance should be noted for.

The way you got into the insurance industry is quite interesting – can you tell us a little bit about it?  

You know, I used to say that after leaving Hollywood as a failed comic and actor, I applied for a very cliché newspaper ad that said: “Insurance Salesman Wanted”.  But after so many interviews and podcasts for my books over the years, it became clear to me that I have admired this industry from the time I was 12 years old and working on a farm in Western Kentucky.

I was standing on a trailer separating tobacco leaves for harvesting when a guy drove up in a brand new four-door Buick with the windows up (which means he had air conditioning ). Out stepped this guy in a crisp white shirt and tie – which prompted me to ask my friend on the hay bale next to me: “What does that guy do?”, to which he replied: “Insurance or something like that”.

So after nearly three decades in Insurance, I can confidently say that – the industry called to me when I was still a teenager – working in the tobacco fields. It just took me another decade to answer that call.

What made you fall in love with the job?

From day one of answering the aforementioned ad, I was hooked. I couldn’t read enough, learn enough and I couldn’t stop telling people about insurance.

The sophisticated risk transfer features we use, the joy of packaging up legal contracts and offering them to the public, all of it, everything from our rich history to how our industry impacts so many parts of the world for good and social betterment.

What has the COVID-19 pandemic been like on the insurance industry in North America?

Certainly, the past couple of years have impacted everyone in different ways. Personally speaking, the entire event drastically changed my leadership style. Pre-COVID, I was hyper-focused on goals, targets, revenue improvement and of course expense management. During COVID, I had to pivot and become more emotionally engaged and compassionate. Maybe our goals had to be dialled back, but our staff needed adjustment time, mental breaks and check-ins to make sure everyone was ok.

I don’t think anyone came out of COVID with the same leadership skills they entered it with. We all had to change. How could we not have and be relevant?

 “Nearly Every Insurance Executive I know – gives back and speaks wonderful things about the spectacularly awesome products we offer.

What are some of the challenges you’ve been faced with and how have you adapted to them?

I think that every firm is wrestling with talent issues. Recruiting new staff, keeping existing staff, fine-tuning a more balanced workplace that is compatible with a shifting expectation. Firms that want to remain relevant have to adapt, enhance offerings, improve messaging and become engaged in not only re-recruiting their existing staff but continually identifying what the next wave of onboarding insurance geeks wants work to look like.

I would submit to your readers that it most certainly begins with a “remote first“ offering where workers may choose to live and work anywhere they want.

You’re also an author of five books, including four #1 bestsellers – tell us a little bit about them.

Thank you for that question and I could spend forever on this, but I’ll try to be succinct.

  • My first book The Art of the Insurance Deal is a look back on insurance firms acquired and lessons learned. It lists more failures than successes and therefore is a great “what not to do” read for anyone in the M&A space.
  • My second book How to Beat Your Insurance Company has a bit of a misleading title (or a hook as my publisher called it). This one is mostly about the value of using a professional insurance representative or agent to get the best value in all insurance purchased.
  • My third book is Tech Enabled, Tech Forward and Tech Shackled. This was a primer reflecting on how integrating tech in our industry should and should not be done.
  • My fourth book Insurance Evolved is another very short primer on where I see our industry in 2025. A date that is rapidly approaching. The content, though brief, is super thought-provoking.
  • Lastly, my fifth book is Moments with Mucka. Though this one has not made it to number one yet, I hope that it will join the other publications one day. Moments with Mucka is about my firm RIGHTURE and our journey to become a highly awarded workplace and technology firm. It includes emails and memos from me to staff in our early days and discusses the operational, cash flow, staffing issues that nearly every agency owner or insurance executive can relate to.

When can we expect a new book and what topic do you plan to explore next?

I think I am always working on the next book in my mind and candidly I am probably already three books ahead in my imagination. The book I am consolidating the most notes about right now is The Rise of the InsurTechs and am quietly speaking to founders I believe are transforming the landscape of how insurance is bought, sold and serviced.

Finally, can you tell us a little bit about this award and what it means to you?

RIGHTSURE has been so very fortunate to be a recipient of so many awards, but the thing about winning is that it never ever gets old.

It is actually quite addicting and pushes everyone at our firm to improve, be better, work smarter and harder.

Winning is for everyone a validation that we are on the right path, working as a team.