Simon Glairy has built a career at the intersection of high-stakes corporate innovation and the gritty reality of hands-on problem-solving. After years of spearheading new ventures within the structured halls of global giants like Johnson & Johnson, Procter & Gamble, and WeightWatchers, he recognized a recurring theme in the human experience: the need for support during life’s most disruptive and confusing moments. This realization eventually led him to the world of property damage restoration and digital health, where he saw firsthand how administrative friction can compound personal stress. Today, as a leading voice in the insurtech space, he is focused on dismantling the operational silos that have long plagued the insurance industry, advocating for a future where technology serves as a bridge rather than a barrier.
In this discussion, we explore the deep-seated challenges of insurance modernization, moving beyond the hype of individual AI tools toward a vision of holistic orchestration. Glairy sheds light on the importance of “operational empathy,” a concept born from thousands of hours spent listening to the frustrations of adjusters and claimants. We touch upon the strategic significance of building trust in a risk-averse market, the common pitfalls of leading with technology rather than solutions, and why the future of claims management depends on transforming static systems of record into dynamic systems of action.
You transitioned from spearheading major ventures in large public corporations like Johnson & Johnson and Procter & Gamble to founding a startup dedicated to fixing operational fragmentation. How did those disparate experiences in corporate America and digital health eventually converge to lead you into the insurance sector?
My career path has been defined by two major chapters that, while different in scale, share a very specific unifying thread. The first half was spent inside the massive machinery of public companies, where I learned how to build and launch ventures that had to withstand the scrutiny of global operations. The second chapter was far more entrepreneurial, involving the co-founding of a digital health startup and managing a private equity-backed rollup in the property damage restoration industry. Throughout all of it, I felt a deep-seated desire to help people navigate those difficult, life-altering moments, whether that was through behavioral science or providing physical services after a crisis. It was during our work in digital health that my co-founder and I stumbled upon the Workers’ Compensation Benchmarking Study, which felt like a revelation. The data painted a picture of a claims process that was not just administratively burdensome for professionals, but genuinely confusing and stressful for the people it was supposed to help, and that was the moment the mission for Crosstie became clear.
Navigating the insurance industry often feels like a marathon due to its traditional and risk-averse nature. What advice would you offer to other insurtech leaders who are struggling to gain traction with their innovations?
If I could sit down with my younger self or any leader entering this space today, the first word I would emphasize is patience. You have to understand that insurance is fundamentally built on risk mitigation, which means changing a process or a legacy system is never going to happen overnight, regardless of how impressive your technology is. You might have built a demonstrably better mousetrap, and your prospective customers might even sit across the table and agree with you, but that doesn’t mean purchasing that tool is going to become a “hair-on-fire” priority for them immediately. My advice is to never confuse novelty with actual value; insurance buyers aren’t looking for the flashiest new gadget, they need solutions that respect their regulatory realities and plug into their existing workflows without breaking them. Ultimately, you cannot growth-hack your way around the need for credibility, so you must earn trust by showing up, being honest about what your tech cannot do, and learning the intricate details of your customer’s day-to-day work.
We are currently seeing a massive surge in AI interest, yet you’ve noted that many discussions are still limited to isolated use cases. How do you see the role of AI evolving in the insurance space over the next five years, particularly regarding the concept of orchestration?
AI will only truly change the insurance industry when it stops being a collection of “cool features” and starts becoming the invisible engine behind the entire workflow. Right now, everyone is talking about small, individual tasks like summarizing a claim file, extracting data from a messy document, or drafting an automated message to a claimant. While those are certainly useful, the real opportunity lies in orchestration—using AI agents to handle the complex coordination work that currently drains the energy of adjusters and service professionals. Over the next five years, we will see AI taking over the routine monitoring of risk signals, updating core systems automatically, and routing documents to the right people without a human having to click a button. This isn’t about replacing the professional; it’s about giving them back their time so they can focus on the moments where human empathy, reassurance, and institutional accountability are absolutely essential to the customer experience.
With so many carriers and TPAs currently stuck in the “experimentation” phase with AI, what do you believe is the biggest opportunity for insurtechs to create measurable value in the next six months?
The next six months will be a turning point for companies that can help insurers move past small-scale pilots and into full production deployments that actually move the needle on ROI. There is a massive gap right now between organizations that have tested a few AI prompts and those that have actually embedded these tools into real, functioning workflows that reduce cycle times or lower costs. Insurtechs that understand the “boring” but vital parts of the business—like change management, integration with legacy tech, and compliance—are the ones that will win in this environment. Specifically in P&C, the pain in claims and service workflows is incredibly visible and measurable, providing a perfect stage for tech that can simplify manual coordination. The opportunity is there for anyone who can solve a specific operational problem quickly without forcing the carrier into a massive, disruptive multi-year transformation project.
You’ve mentioned that leading with technology rather than the problem is a common mistake in this industry. Why do you think so many startups fall into this trap, and how does it impact their relationship with potential insurance partners?
It is very easy to fall in love with your own tech, especially when you are using powerful words like “agentic” or “AI-powered orchestration,” but those words don’t actually tell a claims leader how their day is going to get easier. The biggest mistake is assuming that a product that looks impressive in a high-gloss demo will actually work when it hits the reality of legacy systems, data constraints, and complex vendor relationships. When an insurtech leads with the technology, they often underestimate the operational complexity that a carrier deals with every single day, which leads to a disconnect that kills trust. The best companies in our space are the ones that respect how insurance work actually gets done and realize that their product must fit into the customer’s current environment rather than demanding the customer change everything to accommodate the software. If you can’t prove that you understand the specific friction in their intake or document processing, no amount of flashy AI will save the deal.
The name “Crosstie” is quite evocative and deviates from the typical tech-heavy branding we see today. What was the intentionality behind that choice, and how does it reflect your company’s philosophy?
We were very intentional about choosing a name that didn’t include the letters “AI,” because we believe that while AI is a powerful arrow in our quiver, it will eventually become ubiquitous and shouldn’t be the core of our identity. A crosstie is the heavy cross-brace on a railroad track that keeps the rails stable and connected so the entire system can move forward safely. That is exactly how we view our role in the industry: as a connective platform that stabilizes the relationship between people, systems, and decisions. We chose the name because it reflects our mission to sit above and between existing systems, bringing order to the fragmentation that usually slows down cycle times. By acting as that stabilizing force, we enable insurers and service providers to reduce their administrative burden and refocus their human talent on high-value work.
When you describe the “operational fragmentation” that your technology is trying to solve, what are the specific pain points that adjusters and claimants are feeling on the ground?
Operational fragmentation is the silent killer of efficiency in insurance, forcing adjusters and service teams to jump between dozens of disconnected screens, manual spreadsheets, and unstructured emails. For an adjuster, this translates to a workday spent chasing information across portals and vendors, constantly documenting phone calls, and manually moving data between systems of record. This chaos isn’t just an internal problem; the claimant feels it too, often left in a state of uncertainty because they don’t know what the next step is, who they need to talk to, or if their documents were even received. Our platform addresses these pain points by automating the routine coordination and providing a guided experience that keeps communication organized and transparent for everyone involved. The goal is to strip away that layers of “busy work” so that the actual process of getting someone’s life back on track can happen faster and with much less friction.
The journey of Crosstie involved a staggering amount of research before a single line of code was even written. Can you talk about those 5,000 hours of interviews and how they shaped the product you have today?
We started the company in 2019, but before we ever sat down to build the software, we spent roughly 5,000 hours speaking directly with the people who live in these workflows every day. We interviewed claimants, adjusters, claims leaders, and various stakeholders across the P&C landscape to understand why the process felt so broken. What we learned was that the problem wasn’t a lack of effort or care from the professionals; it was simply that they were drowning in a sea of fragmented documents, voice messages, and legacy portals. We originally built the company out of Harvard’s Innovation Lab with a focus on a “TurboTax-like” experience for claimants, which went live with our first customer in early 2020. However, as we grew, we realized that the adjusters were just as underserved as the claimants, which led us to expand into a much broader workflow platform that connects every person involved in the claim journey.
With a team of 28 people based in Cambridge and the support of major investors like General Catalyst and MassMutual Ventures, what is the core focus of your primary line of business today?
Our primary mission is serving as a claims and service workflow platform specifically tailored for the P&C insurance market, supporting carriers, TPAs, MGAs, and self-insured organizations. We have built a team of 28 dedicated professionals in Cambridge, Massachusetts, who are focused on building a layer that sits above existing core systems to connect everything from intake and document processing to voice and messaging. We help our partners automate the coordination across their various stakeholders, ensuring that data moves seamlessly between claimant portals, loss control teams, and internal databases. By having investors like General Catalyst and MassMutual Ventures, along with a group of seasoned insurance veterans, we’ve been able to ensure that our technology is built to handle the extreme operational complexity that this market demands.
What is your forecast for the future of claims technology over the next several years?
I believe we are entering an era where claims technology will move definitively from being a passive “system of record” to an active “system of action.” In the coming years, platforms will not just store data; they will move toward deep claims intelligence, using risk signals and behavioral insights to provide next-step recommendations that route work more effectively than ever before. We will see the expansion of loss control as a fundamental part of the workflow, where data from field inspections and remediation efforts informs underwriting and risk decisions in real-time. The future of this industry will be a hybrid model where AI agents handle the vast majority of routine coordination and complex data analysis, while the human professionals remain the indispensable heart of the operation. By automating the mechanical parts of the job, we are actually making the industry more human, allowing professionals to be present for the policyholders when it matters most.
