Rewiring the engine of transportation insurance from within

IN Partnership with

At InsureLine Empire, aligning underwriting, safety, and claims within a single system is improving decision-making, reducing delays, and delivering more consistent outcomes for transportation fleets

MOST TRANSPORTATION insurance programs are stitched together from three separate worlds: brokerage systems on one hand, insurer underwriting platforms on the other, and claims operations that sit somewhere else entirely. For the most part, the siloed approach is manageable – until something goes wrong. Then the gaps become visible. Years ago, working as a broker, Gary Dhillon, president, Insureline Empire, found himself in repeated disputes over claims that stalled in towing yards or storage facilities. Trucks would sit, costs would climb, and no one involved had the authority to move the file forward quickly. Jennifer Jubinville was often on the other end of those calls.

Gary Dhillon opened a new brokerage in 2009, with no clients or staff, focused on acquiring referral business. The brokerage began specializing in transportation by providing exceptional customer service and exclusive insurer arrangements at the onset of the hard market in 2017. The Yatara Inc. tech platform and Yatara Claims Inc. were launched in 2022 and 2023, respectively, to manage the growing operation and deliver an integrated solution for clients, brokers, adjustors, and insurers. InsureLine Empire’s mission is to provide expertise and knowledge to revolutionize transportation insurance management and settle insurance claims in a fair, efficient, and ethical manner, ensuring compliance with policy terms while mitigating risk for the insurer.

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Where the model differs

One system, not three: Brokerage, underwriting, safety, and claims operate within the same platform: Yatara

“[Yatara] handles safety and compliance, and clients can manage their insurance online. They can generate documents and deal with routine changes without calling the brokerage … A truck grosses about $25,000 a month. If it’s sitting still, every day matters”

Gary Dhillon, Insureline Empire

“I didn’t like Jen in the beginning,” Dhillon says, recalling those early interactions. The files were stuck, the costs were rising, and neither side could resolve the issue within the constraints of the system they were working in. That changed once he saw how she operated inside those constraints. Today, Dhillon is unequivocal in his assessment. Jubinville, he says, is “the best transportation adjuster I’ve ever worked with or seen.” On the claims side, Jubinville has seen the same problem from a different vantage point. “You’re trying to do your job, but there are all these external factors slowing everything down,” she says. “The client isn’t happy, the broker isn’t happy, and you’re the one delivering the news.” A long-time transportation adjuster who now heads Yatara Claims, Jubinville describes the core job as straightforward in principle: protect the insurer’s money, keep clients confident that they are being treated fairly, and maintain relationships on all sides. In practice, she says, a maze of disconnected systems and slow internal pathways often prevents adjusters from doing that work cleanly. Both sides of the table agreed: there had to be a better way.

In the conventional model, the broker’s BMS is built around internal workflows, the insurer’s platform is built around policy administration and regulatory reporting, and the adjusting firm’s claims system is built around volume processing. Interfaces are limited and usually one-way. It is not unusual for an adjuster to be working on a serious loss without full clarity on how the risk was underwritten, or for an underwriter to see emerging loss patterns months after they have shifted. Yatara serves as the broker management system, the underwriting tool, and the claims portal for the Empire program. Accounts are quoted, bound, serviced, and adjusted in one environment. Underwriters, brokers, clients, and adjusters see different front ends, but they are interacting with the same data.

On the client side, that supports a level of self-service that is rare in commercial fleets. Dhillon points to personal auto portals where customers can add vehicles and drivers online. “Personal auto is not that complex,” he notes. Transportation is. Empire focuses on fleet business only and uses Yatara to give those fleets direct control over routine insurance tasks. Safety and operations teams can add and delete units and update drivers with swift underwriting approval. They can obtain certificates and binders instantly, all without phoning the brokerage for each change. Dhillon points to the operational demands of fleet clients as the clearest example. Certificates, endorsements, and compliance documentation are not occasional requests. They are part of daily operations, often tied to contracts that depend on immediate confirmation. “It handles safety and compliance, and clients can manage their insurance online,” he says. “They can generate documents and deal with routine changes without calling the brokerage.” That shift becomes more significant after a loss. “A truck grosses about $25,000 a month,” Dhillon says. “If it’s sitting still, every day matters.”

Underwriters benefit from the same integration. Because all underwriting, safety, and claims information lives in Yatara, Dhillon and his team can monitor live loss ratios, segment performance, and driver-level patterns across a large fleet portfolio. “We follow the data, we follow the math,” he says. The team monitor it constantly, looking for trends, and deliberately try to play devil’s advocate against their own conclusions. When early data pointed to a shift in one segment, they changed pricing and appetite quickly. The result was a tangible improvement in loss ratios, even though the program was already profitable. That kind of near real-time adjustment is difficult when underwriting, safety, and claims are running on separate systems with separate reporting cycles.

“The technology supports the way we actually work. You can gather the information, make decisions, and move the file”

Jennifer Jubinville, Yatara CLAIMS

For Jubinville, the distinction is immediately recognizable. Transportation claims tend to expose the limits of traditional structures because they require coordination across multiple parties, often under time pressure. “We’re working with clear policy wording and direct communication with underwriting,” she says. “You’re not trying to track down answers.” Her point is not that claims are simpler, but that fewer obstacles sit between the adjuster and the decision that needs to be made. That difference shows up in consistency as much as speed. When adjusters are working with familiar wordings and direct access to underwriting, the variability that often appears across files begins to narrow. “The technology supports the way we actually work,” she says. “You can gather the information, make decisions, and move the file.” That alignment extends beyond the adjuster. Clients can see the status of a claim, provide documentation, and understand what is required without relying on a chain of updates moving through the broker. The Yatara portal gives clients visibility into the status of their claims and makes it clear what documents are required. Dhillon stresses how important it is that clients “know what they need to do” so they can prepare information in advance. In transportation, that preparation shortens cycle times, reduces friction between carriers and shippers, and improves the likelihood that a good customer retains important contracts after a loss.

Underpinning the model is a particular culture. Dhillon acknowledges that “everyone uses the buzzword ‘culture,’ ” but he is explicit about what matters in practice. “Everyone leaves their ego at the door,” he says. He learns from the safety team, from underwriters, from claims. Dhillon has built a team of specialists with decades of experience as drivers, fleet safety leaders, and regulators. Their work begins with thorough operational audits that go far beyond basic file reviews. They look at how a carrier

Where most programs slow down

Reframing claims as the product

Published April 13, 2026

Shared data across functions

Client-side access to insurance operations

Claims integrated into the workflow

Faster claims resolution reduces downstream cost

Operational BEnEFITS for carriers, MGAs, and broker partners

Improved loss ratio visibility

Greater underwriting discipline

Reduced administrative friction

Stronger client-retention dynamics

Safety, selection, and the discipline of saying no

actually runs: hiring practices, routing, maintenance, training, and compliance culture. These audits serve two purposes. The first is risk selection. Dhillon makes clear that the program will not chase volume if the price is wrong or the underlying operation does not fit. He points out that a small minority of clients often generate a disproportionate share of losses. The simplest way to improve performance is to avoid writing those accounts in the first place, even when premium is attractive. The second purpose is improvement. The safety team do not disappear once a policy is bound. They maintain contact with fleets throughout the policy term, focusing on practical changes that reduce frequency and severity. That year-round presence is made easier, not harder, by the fact that safety, underwriting, and claims all work within the same platform and share the same economic target. Crucially, that discipline extends to premium leakage. The program does not rely on additional broker or service fees that skim off what should be risk premium. Every dollar paid by the client is intended to flow through to the insurer, subject to standard administration. When combined with leaner claims costs and more selective underwriting, that structure allows InsureLine Empire to deliver loss ratios that Dhillon describes as materially better than industry norms, while still offering stable terms to fleets that perform well.

For brokers and insurers, the value lies in stability. When claims are handled efficiently, premium is not diluted by unnecessary leakage, and undesirable accounts are filtered out early, a transportation book can deliver results that justify long-term commitment instead of cyclical contraction. Most importantly, the model reframes complexity. Transportation insurance will remain intricate, with dense regulation, multi-party contracts, and high-severity risk. The question is whether that complexity works against everyone involved or in their favour. By replacing three separate worlds with one platform, giving adjusters a system built around their job, and treating safety and data as continuous disciplines, Yatara demonstrates that complexity can be managed in a way that serves fleets, brokers, adjusters, and insurers at the same time.

Making complexity work for everyone in the chain

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