This is the Way: Jeff Arnold of RightSure Insurance Group

November 6, 2019

This is the Way Header Image for Jeff Arnold

Jeff Arnold grew up in rural Western Kentucky, a place of unlocked doors and southern hospitality.

Growing up, his family was a combination of preachers, farmers, and career military with a sprinkling of some new kind of thing called entrepreneurs.

Arnold’s career in the insurance joint ventures vertical started by accident. After serving in the US Army, he pursued showbusiness in Tuscon, Arizona.

“I had been doing minor local TV stuff,” said Arnold. “Stand up comedy in different clubs throughout the southwest and a few military base tours. I had zero gigs lined up and needed to eat, pay rent, put gas in car, insert other necessity.”

So, like any young man desperate for work, Arnold responded to an ad for a position as an insurance salesman.

“From day one of my new career I was hooked,” said Arnold. “I could not read enough, learn enough or digest enough about this wonderfully exciting industry you casually refer to as insurance, but I call giver of life, dream fulfiller and industry of all things sexy, exciting and just plain awesome.”

With the same missionary zeal and the military discipline of his family, Arnold began to tell anyone who would listen about insurance. He also began to apply principles of entrepreneurship to insurance, and his first joint ventures were born.

“I have been fortunate to do joint ventures with banks, credit unions, mortgage firms, online search engines, auto dealerships, privately-held money funds, publicly-traded aggregators, and some really neat reinsurance stuff with billion dollar companies.” said Arnold.

When asked what he loves most about working in insurance, he recounts the tried and true method of recruiting new college graduates:

“If you are interested in law,” said Arnold. “Guess what, we sell legal contracts. So you can be involved in the creating and distribution of legal contracts.”

He goes on. Want to be a teacher? Well, insurance is the very best for teaching as so few people know much about insurance. The industry needs teacher mentalities to education the public and clients.

What if you want to be police officer or investigator?

“May I introduce you to an industry that needs the best detective minds,” said Arnold. “As we are a target for nefarious actors trying to remove claims dollars in the form of fraud.”

If you are driven by interaction with people and sales personalities, according to Arnold, there is no better industry for you to be engaged with.

“And if leadership and management are your aspirations,” said Arnold. “Start your career here, as the insurance industry is rich with fantastic leadership, mentoring and training opportunities.”

This is the way Jeff Arnold works.



Tucson Arizona, but my firm is licensed in 42 states.

Current gig:

President of RightSure and “Insurance Thought Leader” according to Amazon book review (giggle)

One word that describes how you like to work.


Current mobile device:


Current computer:

Lenovo Thinkpad

Project(s) you’re currently working on:

My third book.

Accomplishments you’re proud of:

Three sons, one daughter and a wife that keeps me around.

jeff arnold family

What are your goals for the next 12 months?

Finalize my third book, acquire a few more agencies and grow our mobile platform for our different web properties (,, and 8 more).

What are your biggest professional challenges?

Literally changing my management and leadership style, which was honed in the 90s and early 2000’s, but required to change. This new generation of millennials and Generation Z just require different way of managing than prior generations. Even the way information is disseminated in our organization has changed from 100 percent email to text message updates, group me conversations, chat room meetings.

Also, amending how I deliver radical candor comments and instant feedback to a generation that needs a compliment or reassurance wrapped up in most communications. It’s not bad, just different. The old direct feedback model doesn’t get received as well in the Millennial and Gen Z subset as it did with Baby Boomers and Gen X.

This is a learning moment for me daily as I struggle to retool my management skillset to be relative with the up and coming workers.

What do you like most about your job?

I truly learn something new just about every other day.

Aside from your phone and computer, what gadget can’t you live without and why?

My key card that I had programmed to get me into home, office, bathrooms, garages etc.

jeff arnold


What technology, apps or tools can’t you live without?

Outlook, and our daily dashboards that measure 92 metrics overnight. I start my day with those metrics.

Describe your workspace.

We have an open office environment. No private offices. My cube is in the middle of our call center in Tucson, AZ, and the only difference in my area is a small set of chairs for conversations and short meetings.

How do you manage your to-do list?

Although I use outlook excessively, my important projects are added to my to do list at the end of each evening, so the next day I know my top items to focus on. I just get it done when I write it down.

What’s your best time-saving tip or hack?

Save your emails for late in morning or day. Email is usually other people’s work. Plan your day and start the work you need to get done before you get to other people’s requests.

What’s the first thing you do when you get in the office?


Jeff Arnold Rightsure insurance

What do you listen to while working?

The chatter of sales and service calls as we are in an open office environment.

What are you currently reading?

As A Man Thinketh by James Allen

Favorite social network?

I’m older so Facebook.

Night owl or morning person?

Asleep by 8, awake at 5.

What are you watching on Netflix right now?

Nothing, sorry.

What does a typical day look like for you?

Start the day with reviewing my to do list, then reviewing analytics and finance reports. Asking myself “What are your big three today? What are the big three items that must get done today?”

Who are your business idols and why? 

Michael Gerber, author of The E-Myth. I got to sit as his feet regularly and learn from him and his proteges.

What is your motto or personal mantra?

If it’s worth doing, it’s worth doing right.

What’s the best advice you’ve ever received? 

Listen much, speak little.

If you could switch jobs with someone, who would it be?

I truly am fine where I am at, and not looking to be anywhere or anyone else.

Who would you like to see in a future This is the Way post?

I am currently very satisfied with the diverse items you have, it’s a fun quick read and there are always good insights.

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