Rising Star Dain Dockter Shares Trends the Trucking and Transportation Industry Should Watch in 2024

Brokering in trucking takes real "salt of the earth" people to understand the complexities and the challenges this industry faces. HUB International's Dain Dockter strives to be just that.
By: | December 1, 2023

Come see the Stars! As part of our ongoing coverage of the best brokers in the commercial insurance space, Risk & Insurance®, with the sponsorship of Philadelphia Insurance, is expanding its coverage of the Rising Stars, those brokers who represent the next wave of insurance brokering talent.

Look for these expanded profiles on the Risk & Insurance website and in your social media feeds throughout 2023.

Here’s our conversation with Dain Dockter, SVP, Midwest territory leader at HUB International, and a 2023 Transportation Power Broker winner.

Risk & Insurance: Can you share with us your brokering journey? How did you find yourself working in insurance and then in transportation? 

Dain Dockter: My journey in the insurance brokerage business started right after I graduated college. I interviewed with a firm after meeting some of their recruiters at a career fair.

I wasn’t pursuing a career in insurance when I was finishing up college, but I was looking for a performance-based career. I started learning more about the insurance brokerage business after I met with some recruiters at a career fair, and as I learned more, it became clear it was a good fit for me.

I gravitated towards the transportation industry because of the people in the trucking industry. They are salt of the earth people, which aligns with who I am.

R&I: What are some of the big trends the transportation sector should be watching as we move into 2024?

DD: 2024 is going to be an interesting year for the trucking industry. There are a lot of “expert” opinions on how 2024 will go, so I am hesitant to make any bold predictions.

2023 has shaped up to be a very challenging year for the trucking industry due to various factors including fuel prices, interest rates, equipment costs, insurance costs; load availability is down, freight rates are down, qualified driver shortage, etc.

I believe Q1 2024 will be a particularly tough quarter for the trucking industry, but then I believe the freight market will pickup towards the end of Q2.

I believe we will continue to see an increase in truck insurance carriers utilizing technology to aid in the underwriting of trucking accounts. There is a big push from insurance carriers to use telematic data from trucking companies in their pricing models.

R&I: In your 2023 Power Broker profile, you are described as going “the extra mile” for your clients. What goes into your brokering style to meet clients’ needs?

DD: It is a lot more than just placing insurance coverage for clients. To be successful in this career, you need to not only have extensive knowledge of the truck insurance marketplace but also of the trucking industry.

I dedicate a lot of time into understanding the business I’m insuring and the challenges they are facing. By doing this, I can help them with more aspects of their business than just insurance.

My team commonly helps our clients with safety, compliance, claims handling, company policies, contract negotiations, acquisitions, etc.

I believe many of my clients view me and my company as an extension of their team, and not just a vendor. There are a lot of times a client will call with an issue or challenge, and there is an “easy” or “textbook” answer that I could provide, but that’s not what the client is looking for.  They want a creative solution or an alternate solution that they may not have thought of.

I think that’s a big reason my clients partner with me.

R&I: What’s a challenge you’ve faced in recent years as a broker and how did you manage it successfully?  

DD: One of the biggest reoccurring challenges I have dealt with in 2023 is the impact that the tough freight market has had on my clients. This has deteriorated some of their balance sheets, which has limited some of their options on how we can finance their risk.

Finding creative solutions for insureds to post collateral, post a premium deposit, or even reduce a monthly installment has been a regular occurrence this year.

I think the key is proactively communicating with a client and walking them through the pros and cons of the options they have.

R&I: You have a few designations under your belt, the CPCU being one of them. How have these helped you in your career journey?

DD: I believe my insurance carrier designations help me more on the insurance carrier side than the client side of the business.

Many of the representatives at insurance carriers I work with recognize that the CPCU designation is obtained by individuals who have the knowledge and discipline to see it through. Having designations behind your name does signify that you are serious about your career and garners a certain level of respect from other professionals in the industry.

Having this credibility helps me when I am negotiating risk financing terms for my clients. &

Autumn Demberger is a freelance writer and can be reached at [email protected].

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