Our new Meet the Insurtech Leader series gives you a look into the minds of the executives guiding these tech-forward companies.
Insurtech founders and leadership are encouraged to reach out to potentially be featured in the series: kaitlyn.mattson@arizent.com.
Who are you and how did you come into your leadership position?
I'm Sean G. Eldridge, the co-founder and CEO of Crosstie.
Before Crosstie, my career had two main chapters. The first was building and launching new ventures inside large public companies, including Johnson & Johnson, Procter & Gamble and WeightWatchers. The second was working in more entrepreneurial environments, including co-founding a digital health startup and leading a private equity-backed rollup in the property damage restoration industry.
The unifying thread across these experiences has been a desire to help people navigate difficult moments, whether through behavioral science and technology or through services that support people after disruptive events. That same thread eventually led my co-founder, John, and me into insurance. We were building a digital health company when we came across the Workers' Compensation Benchmarking Study, which described a claims process that can be confusing for claimants and administratively burdensome for the professionals trying to help them. That problem became the foundation for Crosstie.
What advice would you give to other insurtech leaders, or to yourself five years ago?
I would tell myself to be patient. Insurance is a traditionally risk-averse industry, so changing processes or systems takes time. Just because you have built a better mousetrap, and prospective customers recognize that, does not mean purchasing that mousetrap becomes a hair-on-fire priority.
I would also tell other insurtech leaders not to confuse novelty with value. Insurance buyers do not need more technology for technology's sake. They need solutions that fit into existing operations, respect regulatory and compliance realities, integrate with legacy systems and produce measurable improvements. The best products in this industry are not always the flashiest. They are the ones that actually get adopted, reduce friction and continue creating value after implementation.
Finally, I would emphasize trust. Insurance is a relationship-driven industry. You cannot growth-hack your way around credibility. You earn it by showing up, delivering, learning the details of your customers' workflows and being honest about what your technology can and cannot do.
How do you see AI changing insurance over the next five years?
AI will change insurance most meaningfully when it moves from isolated tools into the workflow itself. Today, a lot of the discussion is still framed around individual use cases: summarizing a claim file, answering a call, extracting information from a document, or drafting a message. Those are useful, but the larger opportunity is orchestration.
Over the next five years, AI agents will handle much more of the routine coordination work that slows down operations: collecting information, checking status, summarizing files, routing documents, answering common questions, monitoring risk signals and updating systems. That work consumes a meaningful share of an adjuster's or service professional's day.
AI will become increasingly capable of handling complex analysis and recommendations, but claims and service will continue to require human empathy and institutional accountability. The most successful organizations will use AI to give professionals more time, better context and stronger decision support, while people focus on the moments where trust, reassurance and care matter most.
What is the biggest opportunity for insurtechs over the next six months?
The biggest opportunity is helping insurers move from AI experimentation to production deployments that create measurable value. Many organizations have tested AI tools, but fewer have embedded them into real workflows in a way that improves cycle times, reduces cost, improves customer experience or gives employees meaningful time back.
That creates an opportunity for insurtechs that understand integration, change management, and have solutions that are built to be enterprise-grade. The next six months will favor companies that can solve specific operational problems quickly, prove ROI and fit into existing systems without forcing customers into a disruptive transformation project.
In P&C, claims and service workflows are especially strong candidates because the pain is visible and measurable. There is still too much manual coordination across calls, documents, messages, vendors and core systems. Insurtechs that can simplify those workflows have a real opportunity to help the industry modernize.
What is the biggest mistake insurtechs make these days?
The biggest mistake is leading with technology instead of the customer's problem. Right now, too many companies describe themselves with the same language: AI-powered, agentic, orchestration. Those words do not tell a carrier, TPA or self-insured what problem is being solved, what workflow is changing or what outcome will improve.
Another common mistake is underestimating operational complexity. Customers have core systems, compliance requirements, legacy workflows, data constraints, vendor relationships, and internal change management challenges. A product may look impressive in a demo but fail if it does not fit the way work actually gets done.
The best insurtechs will be the ones that respect how insurance work actually gets done. That means understanding the customer's current environment, integrating into it and proving value before asking the organization to change everything around the product.
Any meaning behind the company's name?
A crosstie is the cross brace on a railroad track that connects and stabilizes the rails so the system can move forward. We chose the name because it reflects our role as a connective platform. Crosstie brings people, systems, workflows and decisions together so insurers and service providers can reduce cycle times, lower costs and give professionals more time for higher-value work.
We were also intentional about not putting "AI" in the name. AI is just one arrow in a solution provider's proverbial quiver, which will become increasingly ubiquitous with time. What will matter more is not whether a company uses AI, but whether your solution solves real customer problems in a measurable way.
What is your primary line of business?
Crosstie is a claims and service workflow platform for P&C insurance. We help carriers, TPAs, self-insureds, MGAs and service providers automate and coordinate workflows across claims and service operations. Our platform sits above and between existing systems and helps connect work across intake, document processing, voice, messaging, claimant and customer portals, claim intelligence, loss control and insurance-native data integration.
What's the origin story of the company?
Crosstie began while my co-founder, John, and I were building a digital health company. We came across the Workers' Compensation Benchmarking Study and were struck by the problem it described: the claims process was often confusing for claimants and administratively burdensome for the professionals trying to help them.
Before writing a line of code, we spent roughly 5,000 hours speaking with claimants, adjusters, claims leaders and other stakeholders across the industry. The stories we heard made clear that the problem was not a lack of care or effort. It was fragmentation. Claimants were often unsure what to do next, while adjusters and claims teams were coordinating work across calls, documents, portals, vendors and legacy systems.
Our initial idea was to build a guided, TurboTax-like experience for claimants, giving people clearer instructions, easier communication and a better way to complete the steps required in a claim. We built the company out of Harvard's Innovation Lab and went live with our first P&C customer in early 2020.
As we worked with customers, we saw that the same fragmentation affecting claimants also affected adjusters, service teams, claims leaders, and other stakeholders. That insight shaped the company's evolution. Crosstie has grown from a claimant experience solution into a broader workflow platform for P&C claims and service operations, helping insurance organizations connect the workflows, systems, and people needed to move work forward.
When was it founded?
The company got its start in 2019. We went live with our first customer in early 2020, expanded from workers' comp into broader P&C over the following years, and rebranded as Crosstie in 2026.
What pain points is the technology trying to solve?
Crosstie is trying to solve operational fragmentation in insurance. Claims and service teams often work across disconnected systems, manual processes, unstructured documents, phone calls, emails, text messages, portals, vendors and reporting tools. That fragmentation creates administrative burden for professionals and confusion for claimants, policyholders and other stakeholders.
For adjusters and service teams, the result is too much time spent chasing information, documenting conversations, coordinating next steps and moving work between systems. For customers and claimants, the result is uncertainty: they may not know what happens next, what information is needed, who to contact or how to take action.
Crosstie addresses those pain points by connecting workflows across systems and stakeholders. The platform automates routine work, guides users through required steps, keeps communication and documentation organized and helps surface the information that matters most. The goal is to reduce cycle times, lower unnecessary costs, improve customer and claimant experience and give insurance professionals more time to focus on higher-value work.
What funding rounds has the company had?
Crosstie has raised two rounds, led by General Catalyst and MassMutual Ventures respectively. Along the way, we've also brought on a select group of insurance industry veterans and technology-focused investors who understand the operational complexity of the market we serve.
What's ahead?
Claims technology is moving from systems of record to systems of action, and Crosstie is building the workflow layer that makes that shift real. That shows up in a few specific ways.
We are going deeper into claims intelligence, moving beyond static summaries toward risk signals, behavioral insights, and next-step recommendations that help work get routed more effectively. We are also expanding loss control into a larger part of the platform, connecting inspections, remediation, employers, underwriting, and risk teams so field data can inform better decisions over time.
On the orchestration side, we are extending Crosstie's ability to trigger actions across our platform, existing core systems and other point solutions, while keeping systems of record updated automatically as work progresses. We are also broadening service and stakeholder workflows so policyholders, agents, employers, and other stakeholders get clearer guidance, easier task completion, and better visibility into status.
Underlying all of it, we believe the future of claims and service will be both human and AI-enabled. AI will take on a growing share of the routine coordination and complex analysis that consumes so much time today, while insurance professionals remain central to the moments that require empathy, trust and institutional accountability.
How many employees does your company have?
Crosstie has 28 team members.
Where is the company based?
Crosstie is headquartered in Cambridge, Massachusetts.
