One Incident Can End It All: What Small Fleets Must Do to Stay Insurable

The Road Less Calculated: How MileMaker Is Fixing the Routing Problem Fleets Don't Know They Have

Mark Lukenbill is the Head of Commercial Operations for MileMaker, the commercial mileage and routing technology that powers Rand McNally. He grew up riding along with truck driver uncles across the lower 48, graduated into freight brokerage during the 2008 financial crisis, and has spent the last six years working across transportation technology from TMS and procurement software to railroad operations before joining one of the most established names in North American mapping. Here's a glimpse of what you'll learn: * [1:51] How summers in an over-the-road cab shaped a career in freight technology * [6:45] Why Google Maps and Apple Maps are the wrong tools for commercial fleets * [9:17] The real cost of letting drivers override commercial routing decisions * [14:34] How MileMaker is integrating with Bosch to add lane-level maintenance cost data * [16:26] Why tech stack hygiene could save your company thousands this year * [18:49] The right way to apply AI in fleet operations enhancing people, not replacing them * [26:38] Why customer service quality is the most underrated factor in tech purchasing * [28:05] Career advice for anyone entering the freight and transportation space In this episode… Most fleet operators assume routing is solved. It isn't. The gap between consumer GPS and commercial routing data is where fines, vehicle damage, and driver pay discrepancies quietly accumulate often without anyone connecting the dots. Mark Lukenbill breaks down why commercial routing is more complex than most people realize, what happens when fleets treat it as an afterthought, and how the right technology applied the right way turns a cost center into a competitive advantage. From AI-enhanced dispatching to tech stack hygiene to knowing when your current vendor has already built the solution you're looking for, this episode is dense with operational insight. Key Takeaways * Commercial routing and consumer GPS are not interchangeable using the wrong tool creates hidden costs that rarely surface as obvious line items. * When shippers base payment on commercial routes, drivers who deviate cost their own companies money without either party realizing it. * Tech stack hygiene regularly reviewing what you actually use and what your vendors have recently built consistently finds savings and surfaces solutions already owned. * AI in fleet operations should automate mechanical tasks to free operator capacity for higher-value work not replace the judgment that complex freight requires. Resources Mentioned * Mark Lukenbill on LinkedIn [https://www.linkedin.com/in/mark-lukenbill-jr/] * MileMaker by Rand McNally [https://milemaker.com/] * SPIDER Driver Training by IMPROV Learning [https://improvlearning.com/] * NAFA Fleet Management Association [https://www.nafa.org/] * Chad Lindholm on LinkedIn [https://www.linkedin.com/in/chadlindholm/]

Guilty Until Proven Innocent: What a 21-Year Trucking Insurance Veteran Knows About Risk That Most Fleets Don't

Kenny Planeta is a third-generation trucking insurance broker with 21 years of experience working exclusively in commercial trucking risk. He began managing a book of truck insurance while still in college, following his father and grandfather into the business, and has spent his career helping fleets understand what is actually driving their premiums — and what it takes to change it. Here's a glimpse of what you'll learn: * [2:17] Why litigation — not accident frequency — is the primary driver of rising trucking premiums * [4:34] Why trucking companies are specifically targeted by injury attorneys * [7:59] A real mediation case: how a minor fender bender became a $275,000 settlement * [13:54] Why trucking accidents almost never go to trial — and what that costs the industry * [18:56] The camera conversation: why not having one is no longer defensible * [25:54] How DOT scores now matter more to underwriters than claims history * [31:26] The profile of a fleet that hasn't felt this hard market — and what they're doing right * [40:41] The one piece of advice every fleet should act on to control renewal costs In this episode… Insurance is not just a line item — it is a reflection of how a trucking operation actually runs. Kenny Planeta has spent 21 years at the intersection of claims, underwriting, and fleet risk, and his message is direct: the litigation environment has fundamentally changed the risk profile of this industry, and the fleets that understand that are the ones holding premiums flat while everyone else absorbs 25–30% annual increases. From a $275,000 settlement on a claim with no documented injuries to the DOT scoring shift that now determines insurability more than loss history, this episode is a clear-eyed look at the financial reality behind every trucking insurance renewal. Key Takeaways * Trucking companies carry $1M+ in coverage — making them the highest-value litigation target in any accident regardless of fault * DOT scores now matter more to preferred insurance markets than claims history * Cameras must be paired with a coaching protocol — ignoring alerts creates negligent supervision exposure * New hires — not inexperienced drivers — are statistically the highest-risk drivers in any fleet Resources Mentioned * Kenny Planeta on LinkedIn [https://linkedin.com/in/kenny-planeta-9654b55b] * FMCSA CSA Safety Scores [https://ai.fmcsa.dot.gov] * SPIDER Driver Training by IMPROV Learning — improvlearning.com * Chad Lindholm on LinkedIn [https://linkedin.com/in/chadlindholm]

One Incident Can End It All: What Small Fleets Must Do to Stay Insurable

Derek Legg is a Commercial Insurance Advisor at Levitt Group of Colorado, where he works with contractor and service fleets across high-exposure industries to manage risk, control premiums, and avoid the kind of catastrophic claims that can shut a small operation down. In this episode of Road Rageous, Derek breaks down the specific vulnerabilities that most small fleet operators are carrying without knowing it, and what they can do about them right now. Derek and host Chad Lindholm cover the risk profile of young drivers in contractor fleets, why cell phone distraction is chronically under-coached, how maintenance habits affect carrier underwriting, and the case for cameras as exoneration tools. They also dig into the MVR gap and the post-incident documentation step that separates clean claims from costly disputes. This episode is built for fleet owners and operators who run without a dedicated safety department. If every insurance renewal feels personal, and every incident hits the bottom line directly, Derek's practical framework gives you a starting point that does not require a large budget or a full-time safety team. Learn more: improvlearning.com/fleet-training | improvlearning.com | levittgroup.com Here's a glimpse of what you'll learn: * The young driver risk that contractors consistently underestimate * Why cell phone distraction is under-coached in small fleets * How vehicle maintenance affects carrier underwriting and premiums * Why post-incident documentation determines claim outcomes * The MVR gap: most contractors hire before checking driving records * How cameras protect and exonerate drivers more than they surveil them * Why nuclear verdicts are no longer just a large-fleet problem * Three specific fixes every 10-truck fleet should make this year

Fleet Is Not the Stepchild: How Knoxville Is Redefining Municipal Fleet Leadership

Fleet Is Not the Stepchild: Nicholas Bradshaw on Professionalizing Municipal Fleet Management Nicholas Bradshaw, Director of Fleet Services for the City of Knoxville, leads a 1,700-vehicle municipal fleet with a philosophy rooted in people-first hiring, life cycle analytics, and innovation. In this episode, he breaks down why fleet gets overlooked, what it takes to change that, and the practical steps he is taking in Knoxville to build a more professional, visible, and financially accountable fleet operation. Here's a glimpse of what you'll learn: * How a career in building inspections and HR led to fleet leadership * Why an HR background changes how you hire and manage a fleet team * Fleet as the invisible backbone of city operations * The case for life cycle data and total cost of ownership modeling * Why fleet is on the leading edge of municipal innovation * How Knoxville is using 3D printing to solve supply chain problems * Telematics, fuel management, and moving from reactive to proactive maintenance * Why fleet technicians are really IT professionals now * Advice for anyone considering a career in public fleet management Key topics include Knoxville's use of 3D printing to manufacture parts in-house during supply chain disruptions, how telematics shifted the department from reactive to proactive, why hiring for attitude beats hiring for credentials, and how fleet managers can make the business case for life cycle replacement funding. Nicholas also shares his perspective on professionalizing the fleet industry through certifications, analytics, and intentional advocacy. If you work in public fleet or are considering a career in fleet management, this episode is a direct and energizing look at why the field matters more than most people realize. Resources: knoxvilletn.gov | improvlearning.com/fleet-training | apwa.net Good to go, or any tweaks needed?

Why Safety Fails When It's Just a Priority: Steven Mock on Risk, Culture, and the Real Cost of a Claim

Steven Mock [https://www.linkedin.com/in/steven-mock-434b6111] is the Risk Mitigation Director at Brown and Brown and a Certified Safety Professional with 18 years of experience in safety training, compliance, underwriting, and fleet risk management. His track record includes taking a fleet from a 300% loss ratio to 21% in three years while tripling its size. In this Road Rageous episode, Steve challenges the assumption that fleet safety is primarily a driver behavior problem. Most claims, he argues, trace back to failures in administrative controls: outdated training, unenforced policies, and telematics systems nobody uses. He makes the financial case for safety as a core value, not a priority, and shares the I-75 collision that permanently shaped how he thinks about defensive driving. Key topics in this episode: * The collision on I-75 that turned Steve from safety advocate to true believer * The picture frame on the visor: building emotional buy-in for safe driving * Why both new drivers and 20-year veterans are your highest-risk groups * Why 85% of insurance claims trace back to administrative control failures * How to use telematics scorecards the same way you use a P&L * The NIOSH hierarchy of controls applied to fleet risk * Safe production versus production at any cost: the math always favors safety * Publicly praise, privately reprimand: leadership lessons from the Marine Corps Connect with Steven Mock on LinkedIn [https://www.linkedin.com/in/steven-mock-434b6111] or email steven.mock@bbrown.com [steven.mock@bbrown.com]. Read the full episode article at improvlearning.com [https://www.improvlearning.com/].