Insurance carriers are in constant battle on the right time to modernize legacy technology. New technologies promise efficiency, speed, and scale, but the industry has been burned by solutions promising the world and delivering a painful implementation. Workflows get disrupted, teams get overburdened, and the cost of “transformation” often exceeds the return.
Why do so many well-intentioned efforts fall short of expectations?
Dave Fernandez, Chief Claims Officer at Kingstone Insurance, has seen it all. With over 25 years of experience leading claims organizations at carriers like Progressive, Liberty Mutual, Unum, and Point32Health, Dave has seen multiple waves of tech transformation and learned how to modernize with intention.
Today, he’s applying that expertise at Kingstone, a regional carrier founded in the 1800s that has sustained its rich history by sustainably evolving to shifting market conditions. The framework Dave uses is rooted in LEAN thinking: easier, then better, then faster, then cheaper. And yes, the order matters.
The trap of "transformation"
On paper, claims transformation seems simple. Eliminate manual work, reduce friction, and give adjusters more time to focus on the hard stuff. But in practice, even the best-intentioned efforts can stall or fall short of their promise.
Many carriers take a tech-first, speed-focused posture. The goal becomes to show progress quickly to validate decision making. This could look like anything from cut costs to boosted throughput. But when the fundamentals aren’t in place, speed just multiplies the problems. The result is transformation that doesn’t transform much at all.
Below are the most common traps Dave has seen claims organizations fall victim to during modernization efforts:
Getting Caught in the Hype Cycle
Transformation has always had a buzzword. In the ’90s, it was digital claims. Then cloud. Then RPA. Then blockchain. Today, it’s AI. Each one arrives with the promise of step-change improvement. But Dave’s watched that pattern repeat long enough to know that tools alone rarely deliver lasting value.
The core mistake, he says, is treating technology as the strategy. Carriers see a new tool, imagine the expense savings, and begin planning rollouts before identifying the real problems they’re trying to solve.
“Carriers bet on the technology. That’s the wrong bet to make. You need to bet on how to win in the business we’re in.”
The risk isn’t in using new tools. It’s in assuming the tool will do the work of defining the right outcomes, mapping the real workflows, and ensuring the solution fits how teams operate. Innovation that isn’t grounded in business context rarely meets expectations built in a pilot environment.
Prioritizing Quick Wins Over Long-Term Value
It’s natural to look for early proof points. Cost savings, faster cycle times, fewer manual steps. But Dave cautions against moving too quickly toward those outcomes before the foundation is ready.
He’s seen how cost-cutting decisions made in the name of progress can create new issues downstream. Teams get leaner before new tools are fully operational. Expectations rise, but the workload doesn’t shrink. In the short term, it looks like a win. Over time, it can erode morale, accuracy, and trust.
“Cutting expenses is like sugar. You see the cost reductions this year, and the pain doesn’t come until six months, 12 months after.”
The pressure to show movement, especially in a hard market or a tight budget year, can decisions that deliver short-term optics at the cost of long-term stability. The challenge is resisting the urge to optimize what’s visible, and instead focusing on what actually drives performance.
Overlooking the Downstream Effects
Transformation decisions don’t happen in isolation. A change to headcount, workflow, or tooling affects everything downstream; from quality control to cycle time to team morale. But those ripple effects are often underestimated.
Dave has seen how easy it is to assume that gains in one part of the process will carry through cleanly. But if teams are asked to do more with less, or if the new tools increase oversight without reducing workload, it can create new points of friction.
What starts as a cost-saving measure can quickly spiral: letters go out faster but contain more errors, adjusters burn out, turnover rises, complaints increase. None of those outcomes are visible in a launch strategy, but they show up in claims performance within a few quarters.
This is why Dave emphasizes sequencing and validation. Before scaling automation or restructuring teams, test the operational impact at a small scale. Make sure it actually helps the people doing the work.
Ignoring the Market Conditions
Even when internal tools improve, that doesn’t guarantee a net gain. Claims doesn’t happen in a vacuum. Contractors, body shops, and vendors all use similar systems, and they evolve alongside carriers.
Dave shared that in some cases, even when internal estimating tools improved, there was little reduction in claim cycle time. Why? Because every other stakeholder was using the same platform. The throughput didn’t change, just the interface.
This kind of ecosystem parity is a silent force that shapes outcomes. Even meaningful upgrades can feel neutral when everyone is modernizing in parallel. That’s why Dave encourages teams to focus less on isolated speed, and more on where they can drive holistic improvement across the entire claims experience.
Dave's 4-Part Framework Bringing LEAN to Modernization Decisioning
So how do you modernize claims without falling into the same traps? At Kingstone, Dave follows a guiding framework rooted in LEAN thinking, an approach developed in manufacturing and widely adopted across industries to reduce waste, improve quality, and drive sustainable performance.
The idea is simple, but powerful: tackle change in the right order.
“Easier. Then better. Then faster. Then cheaper.”
That’s the sequence. And according to Dave, the order is everything. Each step builds on the last. Skip one, and you may save time in the short term, but the long-term impact rarely holds. “If you start with cheap,” he says, “you usually get none of the benefits.”
Let’s walk through what that looks like in practice, using one of the highest-volume, highest-friction workflows in claims: outbound letters. Every carrier writes them. Every adjuster touches them. And every inefficiency, if left unresolved, compounds fast.
Easier: Solve for the Adjuster First
Every transformation effort touches the front lines. And in claims, that means the adjuster. That’s why Dave starts by asking one question: how do we make their work easier?
That could mean fewer systems to log into. Simpler templates. Less time spent formatting documents. Or just clearer visibility into where things stand. But until the work itself feels more intuitive, no amount of automation will deliver real value.
“How do we make this easier for the customer? How do we make this easier for the adjuster? Because if you make it easier for them, you’ll make it better for them. You will make it faster for them.”
Too often, carriers chase operational lift without first removing the daily friction adjusters face. Dave flips that order on purpose: reduce the drag, then everything else gets lighter.
Better: Build Accuracy into the Process
Once the work feels easier, the next goal is quality. For Dave, “better” means more accurate, more consistent, and more resilient workflows.
It’s not just about fewer mistakes, it’s about predictability. Adjusters need to know that the tools and templates they’re using are correct. Supervisors need to trust the drafts. Customers need to receive letters that match policy language and intent.
When transformation skips this step, you end up with “faster” processes that quietly erode quality. More errors. More rewrites. More frustration. That’s why Dave prioritizes clarity and oversight before scale ever enters the conversation.
Faster: Scale What Works
Once a process is easier and better, then it becomes scalable. That’s when automation actually works.
In Dave’s experience, teams that jump straight to faster often find themselves caught in cleanup. By contrast, when speed builds on solid ground, it feels almost natural. Throughput increases because there’s less friction and fewer blockers.
In practical terms, this could look like pre-filling fields, batch-generating documents, or auto-triggering standard communications. But only after those workflows have been stress-tested and proven sound. As Dave sees it, velocity without validation is just risk in disguise.
Cheaper: Let Savings Be the Byproduct
Cheaper isn’t the goal, it’s the reward. Everyone wants to see ROI. But Dave’s firm belief is that cost savings should be the last benefit to arrive, not the first goal to chase.
Too many carriers reverse the sequence: start with cheaper, then figure out the rest. But Dave’s seen how fragile that approach is. Short-term cuts often create long-term costs such as burnout, turnover, compliance issues, and rework. And by the time those show up in the data, the budget cycle has moved on.
“If you start with cheap, you get none of the benefits.”
By starting with easier, then improving quality, then building speed, Dave’s teams earn their efficiency. The savings are real, but they’re sustainable, not superficial.
Taking the First Step Toward Change
Most carriers don’t wait because they’re unsure whether to modernize. They wait because they’re unsure how to do it without regret. The fear is that any upgrade means disruption, pain, and long timelines before value shows up.
Dave sees it differently. When you follow the right sequence (easier, then better, then faster, then cheaper), you can move fast and with purpose. The framework is not just theoretical. It is how you protect your team, your service, and your momentum during change.
At Kingstone, Dave put that into practice. His team went live with both a new claims system and Kyber in under 2.5 months. By focusing first on what made life easier for his team, they are now seeing improvements across the board: better quality, faster workflows, and long-term savings.
Read more to learn how Kingstone went live with Kyber in 2.5 months, or book a demo today to see how you can automate your claims process.
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