Every CFO Needs a Risk Manager Like Jake Taylor

Every Part-Time CFO Needs a Great Jake Taylor

The biggest frustration of leaving the corporate world to start a CFO practice is leaving behind all the great resources we had easy and quick access to.

We’re not just starting over in terms of building a new career. We’re also having to create a network of experts from the ground up–no easy task.

Meet Jake Taylor

The resource I missed the most in the W-2 world was the risk management team that looking back, I took way too much for granted.

Many of my first clients were clueless regarding their commercial insurance packages. Me too. Ditto for the insurance agents. Ouch! Is that harsh? Maybe, maybe not.

Most of the early agents I worked with were not insurance experts let alone consultants. They were sales people. And I still encounter this issue today. Once the insurance package is renewed, we never hear from the agent until a year later.

All that changed when I met the brother of a prior client. This guy knew insurance like the back of his hand. He didn’t just sell insurance. He taught it. He explained it. He broke down complex language and concepts into simple terms.

I was smitten with awe. I wanted this guy at my fingertips anytime I had a risk management question. I wanted every current and future client to have access to this extraordinary resource. The insurance superman I’m describing is Jake Taylor of Winter Dent Company in Columbia, Missouri.

I appreciate Jake’s uncanny ability to explain the strengths and weaknesses of any insurance package in simple, everyday language. Plus, he’s never heard a dumb question. If needed, he’ll answer the same question multiple times until the I-got-it-aha-moment sinks in.

Why had I not met other Jake Taylor-like professionals before? Because they are rare and hard to find.

Can Your Risk Manager Handle Any Problem?

My Favorite Jake Taylor Story

Several years ago, I asked Jake to look at the risk management package of a client where we had some serious holes in our cyber coverages. At the time, cyber policies were still relatively new products. Experts were hard to find, and I personally believe that’s still the case today.

Before Jake gave his professional opinion, he didn’t attend one conference, but two in order to learn the nuances of cyber insurance. It’s stories like this why I refer to him more as a consultant than a salesperson peddling commercial insurance packages. And that’s exactly the type of resource you need access to in your CFO consulting practice.

The Most Important Lesson I’ve Learned about Insurance

Most small businesses set it, then forget it. That is, they buy/renew insurance and forget it till the following year (unless of course there’s a claim).

This mindset needs to change. The small business owner does not have time to think about insurance. Why should they? They are in the business of building a valuable business. And that’s where we enter the picture. We need to take a holistic approach to risk management by being proactive and understanding where risk exists throughout the companies we serve.

After dozens and dozens of discussions with Jake Taylor, I’ve learned the essence of risk (once identified) can be boiled down to four key verbs:

  • absorbed
  • minimized
  • transferred
  • avoided (at all costs)

I’ve created my simplistic matrix which serves as my mental model for classifying any type of risk I identify:

Risk Management Matrix

The goal is not to become a Jake Taylor, but to learn enough about risk management to know the right questions to ask as you are quarterbacking the insurance process for any client you serve.

Insurance Resources

I encourage you to have the following resources at your fingertips if your risk management awareness and acumen is weak.

The first is a free downloadable PDF called Risk Management Made Easy by Andy Osborne.


The second resource is a book entitled Insurance: A Big Decision for Small Business. It’s a book heavy on terminology more than anything. If insurance is new for you, read this little book.

And sorry everyone, Jake Taylor is not a resource–he’s mine.

Seriously, if you are looking for a Jake Taylor in your area, he’s the kind of person you can ping on LinkedIn, and I’m sure he’ll find a resource that can help you.

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *