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

Promotional graphic for Work Truck TruckChat’s “Shades of Fleet: Pride in Motion” series featuring a close-up of a moving truck tire on a highway at sunset, bold white lettering, and subtle rainbow motion graphics on the right side.
Operationsby Lauren FletcherMay 22, 2026

Work Truck Seeks Industry Voices for ‘Shades of Fleet: Pride in Motion’

Share your story in Work Truck’s new “Shades of Fleet” video series, spotlighting real voices, experiences, and perspectives across fleet.

Read More →
An infographic from Verisk’s CargoNet shows cargo theft trends for Memorial Day weekend, including 221 reported incidents, the top-targeted states, common theft locations, commodity types, and an estimated total loss value exceeding $27 million.
OperationsMay 22, 2026

Verisk CargoNet Warns of Selective Cargo Theft Targeting During Memorial Day Period 2026

Verisk CargoNet analysts are observing a broader shift in cargo theft behavior and expect elevated holiday theft risk during the Memorial Day period, which runs through next Wednesday, May 27.

Read More →
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 FletcherMay 19, 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 →
Ad Loading...
Lauren Fletcher poses beside a bold “Truck Chat Weekly Cheat Sheet” graphic featuring this week’s topics: reliability, rising fleet salaries, and right-sized engines against a moving truck background.
Operationsby Lauren FletcherMay 18, 2026

Fleet Reliability, Rising Salaries, and Right-Sized Engines | Weekly Cheat Sheet

Fleet manager salaries, truck reliability, Cummins’ X10 engine, GM Fleet vans, diesel trends, and more in this week’s Truck Chat recap.

Read More →
Podcast thumbnail for The Chatty Chassis with Lauren Fletcher featuring the headline “Fleet Doesn’t Really Retire. It Rewires.” alongside a desk scene with a coffee mug reading “Not Retired. Rewired.”, fleet truck photos, and a notebook listing experience, perspective, purpose, and staying in the game.
OperationsMay 13, 2026

Fleet Doesn’t Really Retire: It Rewires.

Fleet professionals don’t really retire. They rewire. A look at why fleet experience, mentorship, and purpose never fully leave the industry.

Read More →
Cover of a whitepaper titled “The Hidden Costs of Departmentally Assigned Vehicles on Your Fleet” featuring a black fleet vehicle driving on a road at sunset. Subheadline reads: “Discover how your fleet can reduce costs and minimize risk by implementing vehicle sharing.” The document focuses on fleet optimization, vehicle sharing, cost reduction, utilization tracking, and risk management for fleet operations.
SponsoredMay 13, 2026

Why Fleet Managers Are Replacing Departmental Vehicles with Shared Motor Pools

Departmentally assigned vehicles often create hidden costs through underutilization, poor visibility, and increased administrative burden. This white paper explores how shared motor pool strategies help fleets reduce costs, improve accountability, and optimize vehicle utilization.

Read More →
Ad Loading...
Lessons that last with Carl Nelson on a historical backround
Operationsby Lauren FletcherMay 12, 2026

What One 40-Year Fleet Career Can Teach You Today

What can a 40-year fleet career teach you today Learn practical lessons on leadership, drivers, and decision-making from Carl Nelson’s experience

Read More →
Lauren Fletcher poses beside a bold “Truck Chat Weekly Cheat Sheet” graphic featuring headlines about AI, technician insights, and fleet industry changes against a moving truck background.
Operationsby Lauren FletcherMay 11, 2026

Why Human Storytelling Still Wins, Plus AI and Fleet Shifts | Weekly Cheat Sheet

AI in fleet, technician realities, diesel trends, GM Fleet vans, and the end of the International CV Series in this week’s Truck Chat recap.

Read More →
Graphic for a Work Truck feature article titled “Everyone Thinks They’re a Fleet Manager.” The image shows bold white and red typography beside a notebook labeled “Fleet Reality” with checklist items including control costs, reduce downtime, manage risk, and keep people moving, surrounded by charts, a calculator, and office workspace materials.
Operationsby Lauren FletcherMay 8, 2026

Everyone Thinks They’re a Fleet Manager

From oil changes to procurement decisions, fleet work is often underestimated by the very people who depend on it most. Bob Stanton makes the case for why communication, not just technical expertise, is one of the most important leadership skills in fleet.

Read More →
Ad Loading...
Graphic announcing a Daimler Truck North America leadership update featuring President and CEO John O’Leary smiling with arms crossed against a blue background, alongside Work Truck branding and title text.
OperationsMay 8, 2026

Daimler Truck Extends O’Leary’s Leadership of DTNA Through 2028

Daimler Truck Holding AG has reappointed John O’Leary to lead DTNA as president and CEO through the end of 2028. He first assumed the role in 2021.

Read More →