5 MINUTE READ
Brandon Littles, Five Sigma’s Global Solutions Expert, joins Cody Eddings and Anis Taylor, Co-Founders of SnapRefund, a unified payments platform for insurers and agents, for a discussion on scaling AI in insurance claims.
Drawing on nearly 20 years of experience across carriers and insurtechs, Brandon reflects on the shift from experimentation to execution, the role of automation in unlocking faster and more accurate claims decisions, and what insurers must do to modernize their claims operations successfully. The conversation highlights why claims are uniquely positioned for AI-driven transformation — and why meaningful progress starts with clarity and commitment.
Brandon’s Journey into Insurance and Insurtech
Cody: Earlier in his career, Brandon built and led high-performing claims organizations at AMICA and INSHUR. Today, he works closely with carriers, MGAs, and TPAs to help them unlock real value from AI and automation in claims.
Brandon, tell us a bit about your journey—how you landed in insurance, and eventually in insurtech.
Brandon: Like a lot of people in insurance, I didn’t grow up planning to be in claims. I started my career right out of college when I was recruited into AMICA. I had a successful career at AMICA, where I held several roles over the years, starting as a field adjuster, then moving into leadership positions as a supervisor and manager. During that time, I really honed not just my adjusting skills, but also my management skills, and developed a deeper understanding of claims and insurance from an executive perspective as well.
Later, I moved into insurtech and joined INSHUR as Head of Claims, where I had the opportunity to build an entire claims organization from the ground up in the commercial auto space. That’s where I really started thinking about how technology could fundamentally change claims operations.
After some time consulting, I joined Five Sigma. I originally selected Five Sigma’s platform when I was Head of Claims at INSHUR, so I had the chance to understand the business from both sides. Being at Five Sigma now has been a great journey—working with carriers, MGAs, and TPAs and helping them modernize claims operations.
Claims Processes Needed to Change. AI is the Key
Anis: You’ve seen claims from every angle: adjuster, leader, consultant, and now technology provider. When did you first realize the process really needed to change?
Brandon: That realization came very early, long before large language models were even part of the conversation.
When I started in claims almost 20 years ago, green-screen systems were still common. Even back then, it was obvious there had to be a better way. Over time, we saw consumer technology evolve: smartphones, cloud computing, intuitive software, while insurance largely stayed the same.
Claims professionals live in the modern world. They use advanced technology in every other part of their lives. Then they come to work and are asked to operate inside systems that feel decades behind. That disconnect has been obvious for a long time.
AI gives us the tools to finally do something about it.
AI Use Cases That Actually Deliver Value
Cody: You see a lot of AI ideas. Some real, some just buzzwords. What’s the most powerful AI use case you’ve seen that actually delivered impact?
Brandon: Two examples stand out.
First is communication triage. Claims are fundamentally a communication business: emails, messages, documents, demands. One customer we worked with had thousands of emails sitting in queues. Clive™, our Multi-Agent AI Claims Expert, helped classify, route, and even draft responses automatically, ensuring messages were tied to the right claims and addressed faster. That alone dramatically increased adjuster productivity and reduced operational times.
The second example is more complex. We worked with a customer who used Clive to analyze high-severity claims and provide structured recommendations. They started seeing six-figure monthly savings, not just from efficiency gains, but from reduced litigation costs and better decision-making.
Where Claims Bottlenecks Really Come From
Anis: From your perspective, where are the biggest bottlenecks in claims today?
Brandon: The biggest bottleneck is indecision.
Claims professionals are careful by nature, and rightly so. No one wants to move fast and make a costly mistake. But that caution often leads to outdated systems staying in place far longer than they should.
What makes it worse is that adjusters know better technology exists. They use it every day outside of work. When organizations don’t modernize, it creates frustration and burnout, and that’s especially risky as the industry faces a major talent gap with retirements accelerating.
A 90-Day Path to AI-Native Claims Management
Cody: If a carrier called you today and said, “We want to go AI-native,” what would a realistic 90-day plan look like?
Brandon: The first 30 days are about discovery and alignment. You need to understand the “why.” Is the goal cost savings? Cycle time reduction? Customer experience? You also assess the current tech stack and identify where automation versus AI makes sense, and where humans must stay in the loop.
The second 30 days are configuration and pilot. You deploy targeted use cases, define KPIs, and start calibrating models.
The final phase is scaling and going live. That includes training, refining workflows, setting up feedback loops, and operationalizing AI governance so the tools can be used responsibly and effectively.
The Biggest Misconception About Claims AI
Anis: What’s the biggest misconception you have to clear up when talking to legacy carriers about AI?
Brandon: That AI is here to take away folks’ job. AI is a tool, just like the personal computer was when it was introduced decades ago. Some tasks will become redundant, but new opportunities emerge for people who learn how to use the technology effectively.
The same thing will happen now. Those who understand how to leverage AI will have more opportunities. Organizations that ignore it risk falling behind.
Why Some Claims Pilots Scale, and Others Stall
Anis: You’ve been on both sides of the table. What separates pilots that scale from pilots that stall?
Brandon: It comes down to understanding goals and commitment.
Successful pilots start with clear objectives and strong collaboration with the vendor. Stalled pilots often happen when organizations want to experiment with AI but don’t invest the time or resources needed to make it successful.
Carriers are busy, and I understand that firsthand. But if you’re going to invest in a pilot, you need to commit fully. Otherwise, it’s unlikely to deliver results.
What Insurance Carriers Need to Say “Yes” to Claims AI
Anis: What do carriers need to see to move from pilot to long-term partnership?
Brandon: Results and honesty.
Carriers don’t want vaporware or overpromising. They want partners who are clear about what their technology can do today, and what’s still on the roadmap. Trust is built by delivering what you promise and being transparent about limitations.
Proving AI ROI to Executives
Anis: What are the top three ROI metrics executives care about most?
Brandon: First: financial impact—loss cost savings, litigation reduction, overhead efficiency.
Second: cycle time. Faster resolution benefits both carriers and policyholders.
Third: accuracy. Speed without accuracy leads to overpayments and leakage. The balance matters.
Lightning Round
Cody: Let’s do a lightning round. First thing that comes to mind.
Most underrated claims metric?
Cycle time.
One process you’d retire tomorrow?
Manually reviewing 400-page demand packages.
One word that defines the future of claims?
Trust.
At the end of the day, policyholders just want legitimate claims paid fairly and efficiently. Everything we build should support that trust.
Cody:
Brandon, this has been an incredible conversation. Thanks so much for joining us.
Brandon:
Thank you. I really enjoyed it.
