For California fleets of 5 to 50 trucks. Bilingual service. 85+ carriers shopping every renewal. 17 years in the Inland Empire.
Fleet insurance isn't a transaction. It's a relationship — with a broker who understands your trucks, your drivers, your lanes, and your goals. Here's what makes Checkers different for fleet operators.
Approximately 60% of Inland Empire trucking operations are Hispanic-owned. We've served this market since 2009 with fully bilingual service — not just translated documents, but native Spanish consultations, claims advocacy, and renewal negotiations. Your drivers, dispatchers, and safety staff get served in the language they operate in.
Unlike captive agents who quote a single carrier, we represent 85+ commercial markets including Progressive Commercial, Berkshire Hathaway GUARD, Great American, CNA, and specialty programs through Lloyd's of London. For fleets with unique profiles — safety issues, specialty cargo, rapid growth — we access surplus lines markets most brokers don't.
Safety scores creeping up? Recent at-fault claim? New drivers under 23? These are the accounts standard brokers decline. They're also the accounts we place every week through surplus lines markets. Your fleet's history doesn't define your insurance — your broker's market access does.
Based in Ontario, California. We attend your safety meetings, meet your dispatchers, and show up when there's a claim. National carriers route you through 1-800 numbers. We route you through John, who's been placing insurance in the IE for 17 years.
Fleet coverage isn't one policy — it's a stack. Each layer solves a specific risk your fleet faces. Here's what we put in place for every fleet we work with.
Primary liability coverage required by FMCSA. $750K minimum, $1M standard for most shippers. Protects fleet from bodily injury and property damage claims caused by your trucks.
Covers freight in transit against fire, theft, collision, and overturn. Typical limits $100K-$250K per load. Required by most shippers and brokers to dispatch loads.
Collision and comprehensive for tractors and trailers. Required by lenders on financed equipment. Deductibles set to match fleet's risk tolerance and self-insurance capacity.
Covers bodily injury and property damage not caused by truck operation — slips and falls at your terminal, damage during loading, premises liability for your dispatch office.
Protection for non-owned trailers you pull under written interchange agreement. Required for port drayage, intermodal, and dedicated contracts at LA/Long Beach and other ports.
Required by California law for any fleet with W-2 drivers. We coordinate with employer's liability and bobtail coverage to ensure no coverage gaps on drivers.
Fleet placements take time to do right. Our process runs 60-120 days before renewal, giving us leverage with carriers and giving you options to compare. Here's what working with Checkers looks like.
We meet at your yard or office. Walk through your trucks, drivers, loss history, current coverage, and the gaps you want to close. We ask questions most brokers don't — lane concentration, equipment age, driver retention patterns, contract minimum requirements.
Week 1We assemble your underwriting package — loss runs, MVRs, financial exhibits, safety program documentation. A clean, well-presented submission earns better quotes than the same fleet submitted messily. We write the narrative that positions your fleet for the best rates.
Week 2We market your account to the carriers most likely to write it competitively. For a clean mid-size flatbed fleet, that's 5-8 standard markets. For a hard-to-place reefer fleet with recent claims, that's 3-4 surplus lines programs. Carrier selection is tactical — we target the markets, not blast the market.
Weeks 3-5We present quotes side-by-side with clear coverage comparisons. Not just price — coverage differences, carrier financial strength, claims service quality, growth flexibility. We negotiate with carriers when there's room, and we tell you when there isn't.
Weeks 5-7You select the carrier. We handle the paperwork, FMCSA filings, certificates for shippers, and cancellation of the prior carrier. Your coverage transitions with zero gap. First certificate of insurance to your top shipper goes out within 24 hours of bind.
Week 8Quarterly check-ins. Loss run monitoring. Mid-term endorsements for new trucks and drivers. Safety program consultations. Pre-renewal strategy 120 days out from your next renewal. This is where the relationship pays off year after year.
Year-roundEvery fleet is different. Here are three recent examples of fleets we've placed — with identifying details removed — to show what's possible when your broker actually shops the market.
Hispanic-owned 28-truck flatbed operation running California and Arizona. Two at-fault crashes in prior year drove standard markets to decline. Their previous broker couldn't find a placement. We accessed Canopius through surplus lines, presented a detailed safety improvement plan, and bound coverage with $1M liability.
Family-run 15-truck refrigerated operation adding 5 trucks mid-policy term. Incumbent carrier wanted 40% premium increase on endorsement. We marketed to 4 reefer-friendly carriers and moved the entire account mid-term with a better rate and expanded reefer breakdown limits.
42-truck LA/LB port drayage operation discovered their current policy had a trailer interchange exclusion — meaning every interchange trailer they pulled was uncovered. We rebuilt their coverage stack with proper interchange, adjusted primary auto to match shipper requirements, and held premium flat.
These are the patterns we see when fleets bring us their existing policies. If you recognize any of these in your current setup, it's worth a conversation before your next renewal.
Your fleet grew from 8 trucks to 22 but your liability limit is still $1M. Today's nuclear verdict environment treats $1M as underinsurance for fleets over 10 trucks. We rebuild the stack with appropriate limits and excess layers.
If you run LA/LB port drayage and your policy has a "trailer interchange exclusion," every interchange trailer you pull is uncovered. One damaged chassis can become a $15K+ out-of-pocket claim. This is the single most common coverage gap we find.
Reefer units cost $15-25K to replace in 2026. Many older policies have reefer breakdown limits of $10K, meaning a total breakdown costs the fleet the difference. We rewrite reefer breakdown to match actual replacement costs.
One $2,500 deductible across a 25-truck fleet means every minor fender-bender costs you $2,500. Structured correctly, fleet physical damage can use aggregate deductibles that cap total out-of-pocket exposure while lowering premium.
Your current broker vanishes when there's an active claim. At Checkers, we sit in on claim calls, push back on reservations of rights, and escalate when adjusters stall. Claims advocacy is where the broker relationship actually pays off.
We specialize in fleets of 5 to 50 power units. Below 5 trucks, the pricing dynamics match owner-operator markets. Above 50 trucks, fleets typically use larger regional brokerages with dedicated risk management teams. Our sweet spot is the 10-40 truck fleet — large enough for fleet pricing advantages, small enough to benefit from a broker who knows your operation personally.
Fleet insurance uses multi-truck underwriting, driver schedules, aggregate limits across vehicles, safety program discounts, and experience-rated pricing based on loss history. Unlike owner-operator policies that underwrite a single risk, fleet policies rate the entire operation and reward fleets that demonstrate professional safety management — things like driver training programs, telematics adoption, and hiring standards.
For standard-market fleets: Progressive Commercial, Berkshire Hathaway GUARD, Great American, CNA Commercial, AmTrust Financial, and Cover Whale. For hard-to-place fleets or specialty risks: Lloyd's of London syndicates, Canopius, Ascot, Markel, and Burlington Insurance. Carrier selection depends on your fleet size, equipment, cargo, loss history, and operating radius — we don't push you toward any single market.
Fleet placements typically run 2-4 weeks from initial consultation to bound coverage, with an ideal start of 60-120 days before your expiration date. Starting earlier gives us more carrier options and negotiating leverage. Starting later (30 days out) still produces viable options but with less room to negotiate. We begin most fleet renewals 90 days before expiration.
Yes. Fully bilingual English and Spanish service for fleet operations — policy consultations, proposal presentations, claims advocacy, and ongoing account management. Approximately 60% of Inland Empire trucking operations are Hispanic-owned, and we've served this market continuously since 2009. Your Spanish-speaking dispatchers, drivers, and safety staff work with us in Spanish when they prefer.
Yes. This is what we do. Fleets with recent at-fault crashes, elevated BASIC scores, or a history of claims often find standard markets tightening or declining. We have established relationships with surplus lines markets that write fleets with safety challenges. Rates are typically 30-80% higher than clean markets, but coverage is almost always available — and the right market relationship can bring rates back down within 12-24 months of improved loss experience.
Schedule a 30-minute consultation with John or Will. We'll review your current coverage, identify gaps, and give you a market read — whether you end up working with us or not.