Work Truck Logo
MenuMENU
SearchSEARCH

Staying Ahead of the Rising Challenges of Complex Risk

Driver shortages, rising repair costs and skyrocketing claims payouts make it more difficult for fleets to find complex risk coverage, but there remains hope for companies that embrace technology, safety, training and data analysis.

by Lisa Paul & Dain Dockter
August 30, 2022
Staying Ahead of the Rising Challenges of Complex Risk

Fleets that are training drivers, engaging available technology, assessing their loss history and putting their best foot forward will be doing everything they can to keep complex risk at bay.

Photo: Work Truck/Canva

4 min to read


Finding adequate and affordable insurance coverage has become a laborious task in recent times for fleet operators, driven by workforce issues and rising costs across the board.

One of the greater hurdles has been the endemic shortage of qualified drivers — and there doesn’t appear to be relief on the horizon. More than 75% of commercial drivers are over the age of 40, and experts predict the industry will need an additional 25,000 drivers each year until 2030 to meet the demand.

Ad Loading...

The inevitable increase of inexperienced drivers — who are 3.7 times more likely to be involved in a crash than more experienced operators — will not help insurance costs.

Meanwhile, the industry has seen juries award accident victims an average of $22 million, a nearly tenfold increase from 2010, according to ATRI researchMedical payments for accident victims continue to rise, and the cost to maintain and repair damaged commercial trucks has jumped 10% from 2021 to 2022.

Taking all these pressure points into account, it’s a wonder that any fleet can find coverage, as underwriters have raised premiums and lowered coverage limits in response.

Managing Complex Risk in a Challenging Environment

The good news is, fleets still have a path to better terms and lower premiums for complex risk coverage if they properly manage their complex risk and proactively pursue strategies to mitigate exposures.

Here are four ways transportation companies can manage complex risk and show underwriters that they’re worth the business:

Ad Loading...
  1. Train and re-train to support a safety culture. With the expected influx of inexperienced drivers, transportation companies must make training and continuing education a priority. Underwriters use several variables to determine each driver’s risk rating and may reject drivers with less than two years of commercial driving experience. Requiring new hires to complete an extensive onboarding program and using technology to identify and correct new hire behaviors can make a difference to carriers. In addition, online insurance dashboards that take multiple risks into account give transportation companies insight into insurance costs and the success of risk management strategies such as additional training.

  2. Identify patterns in loss history. Review past claims, noting those that are aberrations and those showing a pattern of behaviors contributing to the loss. By evaluating these claims, organizations can identify the root causes of the loss and implement changes to prevent future incidents. For example, an organization that sees an increase in accidents from brake failures can reduce risk by improving its maintenance and inspection program. Dissecting any large claim can help show how to avoid a repeat.

  3. Use technology to lead to truth. Many insurance carriers are requiring fleets to install telematics to monitor driver behavior, and some are incentivizing policyholders who install front-facing and driver-facing cameras. Telematics can identify and help address driver errors such as speeding, hard braking and sudden swerves. And cameras can reduce the likelihood of a nuclear verdict from even being filed, showing hard evidence of what happened at the time of an accident. New integrations with camera technology can push the video automatically to first notice of loss claims reporting to adjusters, who can then lead to faster and better identification for defense for transportation companies.

  4. Share your safety success stories. Commercial auto insurance premiums are rising and insurers expect organizations to prove that they are mitigating their complex risk. Showing progress in training programs and the use of technology to reduce accidents — while demonstrating revenue and leadership stability — will make an organization more attractive to underwriters.

Risks that come with owning and managing trucking operations are complex. There’s no way around it. Fleets that are training drivers, engaging available technology, assessing their loss history and putting their best foot forward will be doing everything they can to keep complex risk at bay.

Want to learn more about how technology and driver behavior data will transform transportation insurance? Learn more today! 

About the Authors:Lisa R Paul, CPCU, is chief strategy officer for Transportation at global insurance brokerage Hub International. Dain Dockter, CPCU, AAIl, AU, is a senior vice president with global insurance brokerage HUB International’s transportation specialty. This article was authored and edited according to WT editorial standards and style. Opinions expressed may not reflect that of WT.



[1] Bureau of Labor Statistics, Occupational Outlook Handbook: Heavy and Tractor-Trailer Truck Drivers, April 18, 2022.

Ad Loading...

[2] Zippia, Professional Truck Driver Demographics and Statistics in the U.S.April 18, 2022.

[3] Fleet Owner, “Driving experience, not age, impacts crash rates,” August 3, 2020.

[4] Commercial Carrier Journal, “Trucking industry imperiled by spike in nuclear verdicts,” November 12, 2021.

[5] American Medical Association, “Cost of Caring,” October 25, 2021.

[6] Fleet Equipment, “Truck maintenance, repair costs continue to increase,” March 6, 2022.

Ad Loading...
Subscribe to Our Newsletter

More Operations

Skyline of London with a blue sky and an inset logo for Kooner.
OperationsMay 4, 2026

Kooner Fleet Management Solutions Expands Internationally with Launch in the UK

Kooner Fleet Management Solutions’ new Central England operations hub establishes a foundation for 24/7 fleet maintenance, mobile repair, and technician development across the UK.

Read More →
Host Lauren Fletcher gestures toward “Truck Chat Weekly Cheat Sheet” graphic highlighting driver input, TPMS benefits, and the end of International CV Series production.
Operationsby Lauren FletcherMay 4, 2026

Drivers Speak Up, TPMS Pays Off, and a Workhorse Retires | Weekly Cheat Sheet

Drivers are shaping fleet decisions, TPMS is delivering real savings, and a key workhorse is retiring. Plus quick hits on data, uptime, and new trucks.

Read More →
Graphic illustration of runners' feet on glowing pavement to the right, a big rig truck on the left, and headline for a virtual 5k to benefit truck drivers.
Operationsby News/Media ReleaseMay 1, 2026

St. Christopher Truckers Relief Fund Launches 2nd Annual Virtual 5K to Support Health and Wellness for Professional Drivers

St. Christopher Truckers Relief Fund’s 2nd Annual Virtual 5K raises funds and awareness for over-the-road truck drivers facing illness or injury, and there’s still time to participate in this year’s event.

Read More →
Ad Loading...
Open glowing book on a wooden table with candles, quill, and maps, with golden light and magical particles rising from its pages in a fantasy-style illustration.
Operationsby Lauren FletcherMay 1, 2026

The Future of Storytelling Still Belongs To Humans

New tools always change the process. They do not replace the instinct. From portrait painters adapting to photography to creators navigating AI, the people who matter most are still the ones who know how to see.

Read More →
“Legends of Fleet” featuring a dark textured background with gold accents, large metallic gold title text centered, and a framed portrait of Carl Nelson with subtitle identifying him as a retired fleet manager, along with Work Truck and Legend logos at the top.
OperationsApril 30, 2026

Carl Nelson's Journey, Sliding into Success | Fleet Legends

With more than four decades of experience across fleets such as AT&T and AmeriGas, Carl built a reputation for doing the work, leading through change, and helping to move the industry forward without ever making it about himself.

Read More →
Breakdowns, data & insights are the topics of the April 2026 Truck Chat Monthly Recap sponsored by Chevron REGI
OperationsApril 28, 2026

Breakdowns, Data Action, and Driver Insight Take Center Stage | Truck Chat Monthly April Recap

In this month’s news recap, we’re digging into why trucks are still failing in the field, how fleets are finally turning data into action, why driver feedback is becoming a critical operational tool, how fleet leaders are finding their voice, and where simple tech like TPMS is delivering real results.

Read More →
Ad Loading...
A graphic image showing charts and graphs depicting cargo theft in the first quarter of 2026.
Operationsby News/Media ReleaseApril 27, 2026

Cargo Theft Incident Volume Falls in First Quarter of 2026

Verisk CargoNet reported that supply chain crime events across the United States and Canada declined by 5.3% in the first quarter of 2026. However, confirmed cargo theft reports rose slightly, by 41 incidents.

Read More →
Graphic promoting Work Truck Exchange with bold text highlighting pre-scheduled meetings, limited spots remaining, and event details for Phoenix, Arizona.
Operationsby Lauren FletcherApril 27, 2026

Limited Spots Remain for Fleet Managers to Attend Work Truck Exchange

Limited spots remain for Work Truck Exchange in Phoenix. Fleet managers can connect through pre-scheduled meetings designed to deliver real solutions fast.

Read More →
Lauren Fletcher presenting Truck Chat Weekly Cheat Sheet graphic highlighting breakdowns, data action, and driver feedback trends in fleet operations.
Operationsby Lauren FletcherApril 27, 2026

Why Trucks Keep Failing, Plus Data Action and Driver Feedback

Fleets tackle breakdowns, act on data, and rethink driver feedback. Plus TPMS gains and key industry shifts in this week’s Truck Chat Cheat Sheet.

Read More →
Ad Loading...
Shades of Fleet Veterans in Fleet graphic with American flags and Work Truck branding highlighting military veterans’ impact on fleet leadership and operations
Operationsby Lauren FletcherApril 24, 2026

Call for Voices: Inviting Veterans in Fleet to Share Their Stories

Veterans in fleet, it's your turn! share how military experience shapes leadership, discipline, and real-world decision-making across today’s operations.

Read More →