Auto insurance has long been one of the most challenging areas for carriers to manage profitably. Even strong books can come under pressure when loss trends shift, claims complexity rises, repair costs increase, or operational friction slows the path from first notice to resolution.
When an auto book moves above a 100% loss ratio, the lessons are rarely theoretical. They come from messy claims, field experience, workflow breakdowns, and the practical decisions needed to turn performance around.
In this live webinar, Samsung Electronics America and InsurTech NY will bring together insurance and technology leaders to discuss what can be learned from underperforming auto books and the claims environments behind them.
The conversation will focus on the processes, practices, and tools that help teams respond more effectively in the field and across claims operations. From mobile-enabled workflows to better communication, documentation, and operational visibility, the session will explore how insurers can support teams working under pressure while improving outcomes for the book.
What You’ll Learn
What unprofitable auto books can reveal
Practical lessons from books under pressure, including claims patterns, operational gaps, and the signals leaders need to watch.
How field experience can inform better claims decisions
Why real-world claim handling, documentation, communication, and escalation practices matter when trying to improve book performance.
How mobile technology can support auto claims teams
Ways mobile tools can help teams capture information, coordinate work, reduce friction, and support faster decisions in the office or in the field.
How insurers can approach turnaround work more practically
Processes and practices that can help teams move from reactive claim handling toward better operational control and improved outcomes.
As a Business Development & Partnership Manager in the Financial Services vertical at Samsung Electronics America, Lay Ling drives strategic growth by building impactful alliances with System Integrators (SI) and Independent Software Vendor (ISV) companies. With experience in consultations, global business and market development across B2B verticals such as technology, and finance; Lay Ling brings a depth of knowledge and experience in helping financial institutions bridge technology with business goals to support their growth.
Dylan Brand is CEO and Co-Founder of Slate Risk and President of Typhon Risk, where he works with MGAs, MGUs, TPAs, and insurance organizations on underwriting, claims, actuarial, and operational strategy. With deep experience across property and casualty insurance, claims operations, litigation, vendor management, and business process improvement, Dylan brings a practical view of how insurers can improve performance in complex books of business. Previously, he held senior claims and operations roles at James River Insurance Company, where his work included claims automation, vendor operations, system implementation, and virtual automobile claims handling..
Chris Boedeker, CPCU, is VP of Claims Consultancy at Reserv, where he advises insurance organizations on claims strategy, operations, and modernization. He brings deep experience across auto, property, sharing economy, autonomous mobility, and insurtech claims environments, including senior claims leadership roles at Waymo and Uber. Chris brings a practical perspective on how claims teams can improve performance, adapt workflows, and manage complex books of business under pressure.
Why Most AI Pilots Fail And How to Make Yours Succeed
A webinar recap featuring Sasha Haco (Unitary) and Kyle Ramsay (Hippo Insurance)
Hosted by InsurTech NY in partnership with Unitary · May 21, 2026
Insurance organizations are investing heavily in AI. Pilots are launched, proof-of-concepts are built, and then — quietly — most of them stall before reaching production. In this webinar, moderator Jeff Goldberg sat down with Sasha Haco, CEO of Unitary, and Kyle Ramsay, Chief Product Officer at Hippo Insurance, to explore what separates the pilots that succeed from the ones that don’t.
The conversation was grounded and practical — no hype, just an honest look at the four failure modes that kill most AI initiatives, what real production deployments actually look like, and what insurers should do differently.
What’s Being Piloted
AI initiatives are running across the whole business, not just claims
The conversation opened with a look at where insurers are actually experimenting. The range is broader than most assume: submissions intake, underwriting, policy administration, reporting, bordereaux, invoice reconciliation, legal admin. According to Sasha Haco, roughly forty percent of MGA employees spend their time on administrative work, and the figure is likely higher for brokers.
“There’s a lot of manual process across the whole business. Claims feels like an obvious one, but underwriting, policy admin, reporting — there’s so much you can automate. Or not, if the pilot doesn’t work or if things aren’t set up for success.”
Sasha Haco, CEO, Unitary
Kyle Ramsay noted that Hippo has been applying AI at production scale across claims, customer service, underwriting, and internal software development. The common thread across all of it is that the use cases with the most impact tend to involve repetitive, structured workflows where the cost of getting it wrong is high enough to demand rigor, but not so catastrophic that automation is off the table.
Build vs. Buy
The calculus is shifting, but the core question hasn’t changed
The build-versus-buy debate has become more complicated with the arrival of AI code generation tools. Kyle Ramsay described a third option — partnering with a vendor who works closely with the organization’s own data and systems, deploying in a “forward engineer” model rather than selling a packaged product.
“The question we ask ourselves: is tech and data a strength of the company? Is the use case deeply embedded in your operational model or proprietary data? If it is, you lean toward building. If there are vendors with greater data advantages or operational expertise, buying makes more sense.”
Kyle Ramsay, Chief Product Officer, Hippo Insurance
Sasha Haco aligned with this framing. Things that are core to what an insurer does — assessing risk, proprietary underwriting logic — lean toward build. Processes that are simply painful and slow, stitched together across five systems that nobody loves, are good candidates for buying. A short-term vendor relationship can also be a way to demonstrate ROI quickly while a longer-term build strategy is developed in parallel.
The key questions to ask
Is this use case part of our competitive differentiation?
Do we have the internal AI and data expertise to build it well?
What is the fastest path to a meaningful business outcome?
Will the work done now — on data, systems, operations — be reusable regardless of the build or buy choice?
Why Pilots Fail
Four things that kill AI pilots before they reach production
Kyle Ramsay laid out the four failure modes he sees most consistently. The first is a lack of clear problem definition and a shared definition of success across the software team, the operations team, and the vendor. When those aren’t aligned from the start, it’s hard to know whether the pilot has succeeded or not.
The second is data quality. Demos almost always run on clean, structured data. Production data is messier, and the gap between sandbox performance and real-world performance is where many promising pilots fall apart.
The third is operational context. AI that works in isolation from the people who will actually use it tends to create work rather than remove it. End users need to be involved in the design, not handed a finished tool and asked to adapt to it.
The fourth is systems integration. If the AI can’t pull data from your policy admin system or write results into your underwriting notes, the workflow still requires a human to bridge the gap.
“There’s such a strong desire to do AI — let’s do it in any way we can. But often there’s not a lot of purpose around how you make that decision. That leads to thin investment spread like peanut butter across everything, and mediocre results.”
Kyle Ramsay, Chief Product Officer, Hippo Insurance
Accuracy vs. Outcomes
97% accuracy sounds impressive. It’s often not enough.
One of the sharpest observations in the webinar came from Sasha Haco: AI pilots tend to fail when the measure of success is accuracy rather than business outcome. A model that is ninety-seven percent accurate might still require a human to review every single output, which means it hasn’t actually changed the nature of the manual workload at all.
“Accuracy is necessary, but it’s not sufficient. What you need is to change the way people are working to produce a real business outcome. It’s so tempting to say ‘our AI is 97% accurate’, but ultimately that doesn’t move the needle.”
Sasha Haco, CEO, Unitary
The practical solution, she explained, is to treat the accuracy problem differently depending on what you’re trying to achieve. If the goal is full automation, the answer is to use deterministic, rules-based software for every step where you can be certain of the output, and only deploy AI for the steps that genuinely require complex reasoning. That way, the human review is reserved for a small fraction of cases rather than everything.
Jeff Goldberg added that vendors sometimes compound this problem by leading with accuracy numbers in sales conversations, when what matters to an insurer is whether a process can actually be automated or only assisted. Those are very different outcomes, and they require completely different implementations.
AI Risk
Managing hallucinations: structure, context, and specialisation
Audience questions during the webinar surfaced a real concern: as the volume of data fed into an AI system grows, so does the risk of incorrect or fabricated outputs. Both panellists addressed this directly.
Sasha Haco described the approach Unitary uses: structuring the AI’s context carefully, and using a decision-tree model where AI is asked a series of specific questions in sequence rather than being handed all documents and all questions at once. This reduces the chance of context overload and keeps outputs more predictable.
“Where there are parts of the process that don’t need AI, don’t use AI. Minimise the exposure of AI as much as possible.”
Sasha Haco, CEO, Unitary
Kyle Ramsay described a complementary approach: creating teams of specialised sub-agents rather than one large generalist agent. One agent might be tasked purely with finding the roof condition section in a document. A separate, more capable model then makes a judgment about what that information means. This keeps each agent operating within a narrow, well-defined scope where hallucinations are easier to catch and control.
The group also touched on the double standard applied to AI errors versus human errors. The panel’s view was that the higher bar for AI is appropriate in a regulated industry, where accountability needs to be traceable. But they also noted that AI has an advantage humans don’t: when an AI makes a mistake, the whole system can learn from it. Human error tends to stay contained to the individual.
Scaling
Successful pilots that never get used
Perhaps the most candid part of the conversation was about a failure mode that doesn’t get talked about enough: AI pilots that technically succeed but never get adopted. The technology works, the accuracy is fine, and then nothing changes.
Sasha Haco identified three reasons this happens. First, the business need was never clearly defined, or the end users who would actually interact with the tool were never consulted during design. When an operational team inherits something built by a vendor and an innovation team, it often creates work rather than removing it. Second, explainability is absent — if a claims handler can’t understand why the AI made a decision, they will override it every time, and the automation benefit disappears. Third, the pilot ran on synthetic or simplified data that didn’t represent real-world conditions, so the effort to move it into production exposes a gap between what was tested and what actually exists.
“If you can’t prove it on a small piece, it’s never going to work on something big. I feel very strongly that big bang is the wrong way to go.”
Sasha Haco, CEO, Unitary
Kyle Ramsay added a structural point: pilots often de-risk the easy version of a use case — one line of business, low-dollar claims, clean data — and then struggle to extend to where the real value lies. Business stakeholders start asking whether the investment was worth it before the hard work of scaling has even begun. The answer is to think about step two and step three of the plan before you start step one.
Case Study
Hippo’s Clara: from FNOL automation to production scale
Kyle Ramsay shared the story of Clara, Hippo’s AI claims agent built to handle first notice of loss for homeowners. The ambition from the start was to handle all FNOL at scale, not just a subset, with no wait times, better customer experience, and a clear escalation path to a human when needed.
Claims leadership was involved from day one, right down to choosing Clara’s voice and the structure of the data she captured. The team trained Clara the way they would train a new employee, reviewing her work and providing feedback before she went live. The result: adjusters handling thirty percent more volume, high customer satisfaction scores, and customers occasionally thanking Clara at the end of a call.
What made Clara work
A clear, ambitious business case — not a technology experiment
Claims leadership involved from design through to training the agent
A single claims platform and strong data foundation built before the pilot
Skeptics converted to advocates by seeing it work, not by being told it would
A clear line of sight to how Clara would extend to more use cases over time
Case Study
Unitary: automating an MGA’s loss runs process in five weeks
Sasha Haco described a project with an MGA whose internal team had been trying to automate their loss runs process for eighteen months. It was a complex workflow spanning multiple systems, but there was genuine buy-in across the organisation to get it done.
Unitary’s team deeply understood the workflow, built the automation, tested it on example data, and went live. The entire process took five weeks from start to live deployment. Within a few weeks, they were hitting ninety-nine percent automation on real data.
“Something that for their team wasn’t a top priority to build themselves, but for us is a top priority because that’s what our business does. That difference meant we could throw everything at it to make it possible.”
Sasha Haco, CEO, Unitary
The headline results were a fifty percent cost reduction and a nineteen percent improvement in broker satisfaction scores, because what had previously taken days now happened in minutes. The MGA also went on to win two Stevie Awards. The outcomes included some that were expected and some that were not — which, as Sasha noted, is often the pattern when automation is done well.
Final Advice
What to actually do differently
Asked to distil their advice into a final takeaway, both panellists were direct.
“Small bites. It has to be something very manageable — no big bang. And really align on what success looks like and what the business outcome is. Drive towards that, not a vanity metric.”
Sasha Haco, CEO, Unitary
“Be ambitious — don’t just try the safe pilot to test the technology. Define success clearly, begin with the end in mind, and define the steps. Then involve users from day one. Trust is very hard to earn after the fact.”
Kyle Ramsay, Chief Product Officer, Hippo Insurance
Unitary builds Virtual Agents that automate end-to-end insurance workflows inside the systems your team already uses. No new platform, no complex integration, no upfront cost.
Sign up today and be at the forefront of the insurance transformation. Together, we’re not just keeping up with the future; we’re making it.
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A webinar recap featuring Jun Yamada (Tokio Marine), Chris Huff (Adlib), and Frederic Stallaert (Paperbox)
Hosted by InsurTech NY in partnership with Adlib · June 23, 2026
Every claims leader is being asked to go agentic. Every auditor, regulator, and plaintiffs’ attorney is asking a different question: can you prove how every decision was made? In this webinar, moderator Tony Lew was joined by Jun Yamada (VP Business Transformation at Tokio Marine Group), Chris Huff (CEO of Adlib), and Frederic Stallaert (CEO of Paperbox) to talk through what it actually takes to close that gap.
The conversation moved through three connected questions: how to build a data foundation agentic workflows can trust, how to design audit trails that hold up to real scrutiny, and what breaks when pilots try to scale. What follows is a chaptered recap of the most useful ground covered.
Trust at Intake
Agents are only as trustworthy as the data you feed them
The panel opened on what Chris Huff described as the most overlooked problem in agentic claims. Insurers are racing to deploy agents on top of intake processes where the underlying documents are messy, multi-format, and often handwritten. The agent inherits every weakness in the input.
Everyone in claims is racing to go agentic. But agents are only as trustworthy as the data that you feed them. It’s pragmatic, but it’s something that’s often overlooked.
Chris Huff, CEO, Adlib
Jun Yamada framed the same issue from a carrier’s perspective. The fastest way to make agentic adoption tractable, he argued, is to stop thinking about end-to-end claims automation and instead decompose the lifecycle into discrete steps: FNOL, ingestion, extraction, validation, triage. Some of those steps are information processing problems, where AI can carry real load. Others involve actual judgment, where the regulatory and litigation exposure means a human has to remain accountable.
That decomposition is also how trust gets built internally. Tokio Marine has been productionizing the lower-risk capabilities first — document ingestion, summarization, validation — while staying cautious on anything that touches adjudication or litigation. Chris reinforced that this pattern is industry-wide, not unique to Tokio Marine, and the reason is structural: regulated industries have spent years building deterministic processes, and agentic AI feels like a move back toward probabilistic ones. The work is putting in place the guardrails that let probabilistic technology produce deterministic-enough outputs to survive an audit.
Stress-Testing the Foundation
How to find out if your data is actually production-ready
Asked what a carrier could do to test whether their data foundation could support AI, Chris was direct: most carriers test on their best documents because they want a great outcome, and that’s exactly why the resulting pilot won’t scale.
If it runs great on 95%, but the 5% challenging documents is where it falls off the rails, then everything gets shut down. You really have to account for that 5% to make sure the 95% can actually go into scale.
Chris Huff, CEO, Adlib
He outlined three concrete tests any insurer can run before committing to an agentic deployment. The first is to pull a representative sample of real intake — handwritten FNOLs, labelled PDFs, 40-page packets stitched from multiple formats — and measure straight-through yield on the worst portion of it. The results will usually be sobering. The second is to calibrate confidence. When the system reports 90% confidence, does that mean it’s right 90% of the time? Those are not the same number, and most teams haven’t checked. The third is the reproducibility test: pick a random claim and try to reconstruct every input, every transformation, every decision, and every output. If that can’t be done in minutes, the system is not production-ready.
Three tests before going to production
Measure straight-through yield on your worst documents, not your best ones
Calibrate confidence scores against actual accuracy — they are not the same metric
Reconstruct a random claim end-to-end in minutes; if you can’t, you’re not ready
The 50% Reality
Straight-through processing is the wrong goal
Frederic Stallaert pushed back on the idea that full automation is the destination most insurers should be targeting. In practice, none of Paperbox’s 75+ insurance customers have asked for fully unattended intake. The thing they’re actually optimizing for is operational efficiency and the quality of customer service — not automation for its own sake.
Realistically, less than 50% can be fully automated. It’s the low-value claims, the easy ones where we don’t want to spend too much time. The question for the policyholder is: do you want your claim to be handled automatically, or would you want a person to look at it? The answer is, it depends.
Frederic Stallaert, CEO, Paperbox
Three things hold back true automation in his experience. The first is multi-document ambiguity: a claim that arrives across five attachments, multiple emails, and a follow-up requires contextual reasoning the model has to do well across all of them, not just one. The second is the persistent reality of handwriting and low-quality scans. The third is ambiguity in business processes themselves — when two claims handlers in the same team use different typologies and label things differently, there’s no standard for the automation to follow. That last point reframes the work: before deploying AI, much of the value is in business process standardization and the governance around it.
The Audit Trail
What an audit trail actually has to do
Jun laid out a five-part framework for thinking about explainability and audit trail in regulated claims environments. The starting point is human in the loop — AI output should never be the sole decision-making instrument, and the adjuster needs to remain accountable. The second is purpose clarity: there’s a meaningful difference between a tool that organizes documents and one that influences valuation or settlement, and that boundary needs to be explicit.
The third is auditability: a clear record of inputs, outputs, human review, and final actions. The fourth is explainability at the business level — not the technical workings of the model, but how the decision can be explained in terms of facts, evidence, and rationale that a regulator or claimant can follow. The fifth is discoverability: AI outputs create new exposure in litigation, and carriers without traceable accountability struggle to respond when a claim is uncovered in court.
Jun’s five components of audit-ready AI
Human in the loop — the adjuster remains accountable
Purpose clarity — explicit boundary between organizing and deciding
Auditability — inputs, outputs, reviews, and actions all on record
Business-level explainability — facts, evidence, and rationale, not model internals
Discoverability — designed for what plaintiffs’ attorneys will ask in court
Frederic added a critical refinement: the audit trail is more than a log. Dumping data as a proof point isn’t enough. It needs to be viewable, workable, and managed well enough that the carrier can respond confidently to difficult questions when they come — not theoretically retrievable somewhere in the system.
The Litigation Asymmetry
The AI gap carriers can’t afford to ignore
The most pointed argument of the panel came from Jun, who described an asymmetry that’s quietly reshaping the economics of defense. Plaintiffs’ attorneys are deploying AI aggressively. Carriers, constrained by regulation and internal caution, are not keeping pace.
There’s a statistic saying that 100% of demand packages are now created by AI. There’s third-party litigation funding. There are VCs investing in AI for plaintiffs. The regulatory field unfortunately governs the insurance carriers and defense more than the plaintiff side. So there’s an exponential gap that’s growing.
Jun Yamada, VP Business Transformation, Tokio Marine Group
Jun’s point to his own group companies has been the same: litigation management is a stated pain point, but the cautious approach to AI on the defense side means every demand packet a carrier receives is now AI-optimized to find the highest-payout angle, while the response is still mostly human. The expense and indemnity curves on litigation are moving in the same direction the plaintiff-side AI investment is, and that correlation is unlikely to be coincidence.
The Shortcut
Logging the decision, but not the evidence
Asked where carriers most commonly cut corners in governance, Chris named one pattern that fails the first real audit: capturing the outcome of an AI decision without capturing what produced it.
Most teams log that an agent approved a claim at, say, 92% confidence, and stop there. What’s missing is the underlying chain of custody — which version of the model ran, on what prompt, with what raw inputs, through what transformations, and why the confidence landed where it did. In the moment, none of that feels necessary. The dashboard passes. The demo looks beautiful. Then the first audit or subpoena arrives and the record is too thin to defend.
If you can’t regenerate the decision from the same inputs and show that lineage, you don’t have an audit trail. You basically just have a receipt. And we all know that’s not enough to carry, especially when you’ve got a plaintiffs’ attorney coming at you.
Chris Huff, CEO, Adlib
The implication is that the chain of evidence has to be designed in from day one, at the field level. Retrofitting it after an incident is not a strategy.
Why Pilots Break
Edge cases multiply, and humans push back
Frederic described two failure modes he sees repeatedly when carriers try to move from pilot to production. The first is mathematical. In a controlled pilot environment, an edge case is something a clever solution can absorb. At scale, edge cases compound — each one triggers a chain of downstream actions, and the work the automation was supposed to eliminate gets replaced by new work managing exceptions.
If you throw any email into ChatGPT or Claude, you’ll get a fairly accurate assessment. But if you do this at company scale, for different business lines, across thousands of edge cases, suddenly you lose the level of control you want to have over what decisions are being made and why.
Frederic Stallaert, CEO, Paperbox
The second failure mode is human, and harder to engineer around. A pilot is usually run by a team that believes in the technology and trusts the purpose. When the same system is deployed to claims handlers and account managers who weren’t part of that team, they often resist it — finding clever workarounds rather than using the system as intended. The implication is unambiguous: if the end users who will actually interact with the tool aren’t involved during the pilot, the project fails after deployment, regardless of how the model performs.
Where It Works Today
Use cases, lines of business, and a concrete example
Both panellists pointed to a similar pattern in where agentic AI is creating real value today. Summarization is effectively table stakes — ingesting 500-page demand packets and surfacing what the adjuster needs in time to respond inside a 24-hour window. FNOL intake is another high-impact area, particularly for CAT response where temporary intake staff often capture incomplete information; agentic systems can come back to claimants with a list of what’s missing instead of accepting whatever was submitted.
Jun shared a particularly vivid example from one of Tokio Marine’s high-net-worth group companies. For property fire losses, an AI tool now scans the claim file alongside fire and police reports, then cross-references the equipment and appliances in the home against active product recall databases. An adjuster handling a $3M+ home fire isn’t going to manually check whether the homeowner’s barbecue or appliances had open recall notices — but the AI surfaces them, opening subrogation paths against OEMs that would otherwise be impossible to pursue.
Frederic noted that the right application of agentic AI varies by line of business. Personal lines claims benefit from heavier automation because customers usually want fast, standardized settlement of low-value losses. Commercial lines claims are more data-heavy, so the value of agentic AI is in structuring and streamlining intake to give the human claims handler the context to decide faster — not in making the decision itself.
Building for What’s Next
Why architecture matters more than it used to
An audience question about lock-in risk — what happens if a third-party API gets restricted or a vendor changes terms — drew an architectural answer from both Frederic and Chris. Five years ago, Frederic noted, the advice to CIOs was to plan an exit strategy from any major technology investment on a five-year horizon. That horizon has compressed to two or three. The implication is that AI infrastructure needs to be designed for swap-ability from day one, with the ability to replace underlying models and providers as accuracy, cost, and policy conditions change.
Chris added a forward-looking framing on how that affects architecture overall: on a go-forward basis, the population of digital workers (agents) will grow faster than the population of human employees. Humans care about UIs. Agents don’t — they care about clean APIs. The investment that gets de-prioritized in most CIO shops today — API management, increasingly via emerging standards like MCP (Model Context Protocol) — is the investment that becomes structurally important next.
One Thing to Do Today
Build the audit trail before you build the agent
Asked what carriers should do starting today to avoid a litigation reckoning later, Chris distilled the panel’s central argument into one line.
The carriers who survive that subpoena will have built the audit trail before they built the agent. Not retrofitting explainability after an incident — that’s the single most important thing to get right.
Chris Huff, CEO, Adlib
Frederic added the second half of the answer. The carriers who survive will also have kept humans meaningfully in the loop on decisions that carry risk — not as a rubber stamp, but as a genuine review.
If the question in litigation is “did the AI make this decision”, and you can respond confidently that this instance was reviewed by a person who agreed with the decision, it’s a completely different discussion altogether.
Frederic Stallaert, CEO, Paperbox
Jun, asked to add to it, declined to add anything: “Chris and Frederic took the words out of my mouth. We should probably take their words and build our governance model around what they said.”
For 20+ years, Adlib has turned the messiest regulated documents — handwritten FNOLs, multi-format packets, low-quality scans — into AI-ready data that holds up to auditor exams. The foundation that makes agentic claims workflows defensible, not just fast.
Sign up today and be at the forefront of the insurance transformation. Together, we’re not just keeping up with the future; we’re making it.
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Protecting Underwriting Judgment in AI-Enabled Workflows | InsurTech NY
Protecting Underwriting Judgment in AI-Enabled Workflows
Moving Beyond Extraction to Intelligent Triage and Governed Decision Support
March 17, 2026
1:00 PM EST
Free
Most insurance organizations have made progress on automation, but underwriting teams still feel the pressure. Documents are extracted, data is captured, yet underwriters remain stuck reviewing and reconciling information instead of making decisions.
The issue is not a lack of technology—it’s that underwriting workflows are rarely designed around triage. Effective automation starts with intelligent triage, allowing underwriting teams to focus their expertise on the risks that truly need it.
In this exclusive session, InsurTech NY and BoundAI explore how data extraction, triage, and policy validation can operate as a connected workflow—giving underwriting teams leverage without sacrificing quality or institutional knowledge.
Mladen Subasic is the Chief Product Officer at BoundAI powered by OIP Insurtech, with over a decade of experience operating at the intersection of insurance and technology. Over the past six years, Mladen has been among the early leaders to successfully move AI-driven insurance use cases from concept into real-world adoption, focusing on building AI-native platforms that augment human expertise and drive operational leverage.
Gabriel Mayer is the Founder and CEO of Tricura Insurance Group, an insurtech company providing liability risk solutions for post-acute healthcare providers. After years optimizing multi-state healthcare operations, Gabriel now focuses on addressing insurance challenges facing skilled nursing and senior living facilities through data-driven underwriting, proactive risk management, and responsive claims support.
Ted Stuckey is a senior insurance executive focused on modernizing specialty insurance distribution through technology and execution. As President of LocalEdge and Head of Digital Strategy at Bridge Specialty Group, he leads digital and operational initiatives that help brokers and agents move faster, work smarter, and compete in a rapidly evolving market.
David Gritz is Co-Founder and Managing Director of InsurTech NY, where he leads initiatives connecting insurance carriers, technology innovators, and industry stakeholders to drive digital transformation across the insurance ecosystem.
What You’ll Learn
Why effective underwriting automation requires intelligent triage, not just better data extraction
How to design workflows that route clean submissions straight through while flagging risks that need expert review
Strategies for maintaining governance over underwriting logic without hard-coding rules into black box systems
How leading carriers are scaling underwriting capacity while protecting institutional knowledge and decision-making authority
Who Should Attend
📋 Chief Underwriting Officers
💻 CIOs & CTOs
🛠️ Innovation Leaders
⚙️ Operations Executives
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As AI continues to permeate the insurance ecosystem, a new term is capturing headlines and strategy decks alike: Agentic AI. But what does it really mean — and is it more than just hype?
In this exclusive session, InsurTech NY and Lazarus AI bring together top enterprise technology leaders to unpack the promise, limitations, and realities of Agentic AI in insurance.
Who Should Attend: 🛠️ Innovation Leaders | 💻 CIOs & CTOs | 🧾 Product Managers | 📈 Strategy Leads
What You’ll Learn
What makes Agentic AI distinct from traditional automation and GenAI models
Realistic insurance use cases: where is it delivering value today — and where isn’t it?
How CIOs and innovation teams are evaluating Agentic AI in terms of risk, ROI, and strategic timing
Whether this is a genuine leap forward — or the latest AI buzzword
John Keddy is the VP of Insurance Solutions at Lazarus AI, where he leads the development of next-generation solutions focused on secure, cloud-first infrastructure for the insurance industry. With a career spanning CIO, CTO, and CISO roles, John brings deep expertise in enterprise architecture, cybersecurity, and scalable platform strategy. He has overseen large global development teams as well as lean, innovation-driven tech organizations. Known for balancing transformation with operational rigor, John is a trusted advisor to companies navigating digital modernization, with a particular focus on applying AI responsibly in high-stakes environments.
Karthik Sakthivel is the Vice President and Chief Information Officer at LIMRA and LOMA, where he leads global IT strategy for the world’s largest insurance industry trade association. With 20+ years in enterprise technology and leadership roles at Liberty Mutual and beyond, Karthik drives digital transformation across member organizations in over 70 countries. A 3× TEDx speaker, ORBIE Award winner, and author, he champions people-first innovation, agile transformation, and forward-looking tech adoption. He brings a sharp focus on how AI, security, and infrastructure intersect with strategy — and how leaders can unlock lasting impact across both business and tech.
Vice President of AI and Analytics | Mutual of Omaha
Mindy Chen is Vice President of AI & Analytics at Mutual of Omaha, where she leads cross-functional teams harnessing generative AI and advanced data to reimagine customer and associate experiences. A Silicon Valley–trained strategist, she’s scaled analytics from startup scrappiness to enterprise scale, helping teams grow from 3 to 34 and revenue from early traction to market dominance. Her work sits at the intersection of data science, consumer insight, and business transformation — delivering not just answers, but action. Mindy brings deep experience across SaaS, insurance, and healthtech, with a leadership style rooted in curiosity, clarity, and commercial impact.
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InsurTech NY events bring together carriers, brokers, startups, and investors to facilitate new relationships and share insights from insurance influencers.
Join InsurTech NY and Verisk Analytics as we explore how Augmented Underwriting blends machine intelligence with underwriter expertise.
Who Should Attend: 👩💻 Underwriting Leaders | 🧠 AI & Data Executives | 🧾 Product & Platform Owners | 📊 Digital Transformation & Innovation Teams | 🏛️ Carrier Strategy & Ops Leads
In an era of tightening margins and rising customer expectations, underwriting teams need more than rules engines and gut instinct. Join us for a fast-paced 30-minute webinar to explore how Augmented Underwriting blends machine intelligence with underwriter expertise to accelerate decisions, improve consistency, and uncover hidden risk.
You’ll get a firsthand look at how the solution surfaces intelligent recommendations, flags anomalies, and delivers contextual insights—right within your existing workflows. Whether you’re looking to boost profitability, streamline submissions, or empower your underwriters, this session will show how you can start making smarter, faster decisions today.
Key Takeaways:
What “augmented” really means (and doesn’t) in underwriting
How to balance automation with human expertise
Real-world examples of improved risk selection and workflow speed
Where to start: tips for phased adoption and early wins
About Verisk Analytics
Verisk (NASDAQ: VRSK) is a leading global data analytics and technology company that helps insurers make smarter decisions across underwriting, claims, and risk assessment. With deep industry expertise and trusted AI-powered solutions, Verisk supports more accurate risk evaluation, operational efficiency, and better outcomes across the insurance value chain.
Vikash Kothari is a sales leader at Anthropic with over 15 years of experience in enterprise sales and go-to-market strategy. A 6x President’s Club winner, he’s led high-performing teams at Slack and helped scale startups like Wyng from the ground up. Vikash specializes in building scalable sales operations and driving growth across AI and SaaS. At InsurTech NY’s Augmented Underwriting webinar, he’ll share insights on creating repeatable, high-impact sales strategies.
Saul Flores is the VP and Head of Product Growth at Verisk, where he leads strategy and commercialization for cutting-edge data and analytics solutions. Formerly a Partner at BCG and Chief Strategy Officer at AKQA, Saul brings over a decade of global experience helping Fortune 500s scale innovation and drive digital transformation. With roots in economics and executive training from Stanford GSB, he bridges business vision with product execution to unlock sustainable growth.
Head of Commercial GenAI Underwriting Assistant | Verisk
Nicole Ricci is Head of Commercial GenAI Underwriting Assistant at Verisk, where she leads innovation efforts to empower underwriters with intelligent tools that drive efficiency and accuracy. With 20 years of experience spanning operations, product strategy, and insurance technology, Nicole excels at translating complex data into actionable solutions. Her deep industry insight and passion for solving customer pain points have made her a key driver of AI-powered transformation across underwriting teams.
Upcoming Events & Programs
InsurTech NY events bring together carriers, brokers, startups, and investors to facilitate new relationships and share insights from insurance influencers.
Webinar: Breaking Free From the Core System Giants
Date: October 9th, 2025
Time: 2:00 pm (EDT)
Cost: Free
In a market defined by rapid change, the most resilient insurers aren’t those who buy the biggest systems – they’re the ones who adapt the fastest. Today, transformation isn’t about overhauling core infrastructure or investing in bloated, all-in-one platforms. It’s about building flexibility into your operations: filling the gaps, enforcing your own rules, and deploying tailored workflows that evolve with your needs.
This webinar, held in partnership with Neota Logic, will explore how leading insurers are shifting from platform dependency to a portfolio mindset.
Who Should Attend: 🛠️ Innovation Leaders | 💻 CIOs & CTOs | 🧾 IT and Process Owners | 📈 Claims, Underwriting, and Policy Admin Teams
What You’ll Learn
Why flexibility—not just scale—is the new currency of operational success
How leading insurers are shifting from rigid platforms to portfolio-based workflows
Real-world examples of no-code and AI-driven tools powering faster adaptation
Frameworks for filling process gaps without ripping out your existing tech stack
Actionable steps to increase speed, reduce cost, and future-proof your operations
Tony Tarquini is a recognized thought leader and strategist in insurance technology, with over 30 years of experience as an advisor, mentor, and conference speaker. He is the co-author of The InsurTECH Book, an Amazon best-seller, and has held senior roles at Pegasystems and Synapse Ecosystems. A former international athlete, Tony brings a high-performance mindset to innovation and market transformation. He is a graduate of the University of Dundee, with executive education from INSEAD and Henley Business School. Tony is a frequent media contributor and is known for delivering sharp, engaging insights into the future of insurance.
Andy has been CEO of Cardinus since 2006. Prior to joining, Andy founded Evolution Underwriting Group, a UK SME insurance operation, was Assistant General Manager at Travelers Insurance UK, and before that was Ecommerce and Global Marketing Director at Independent Insurance plc. He is Past President of the International Institute for Risk and Safety Management (IIRSM) and Past President of the Insurance Institute of Peterborough and was a trustee of The Alchemy Charitable Trust and The Insurance Charities. He has also been a non executive director of a number of companies.
InsurTech NY events bring together carriers, brokers, startups, and investors to facilitate new relationships and share insights from insurance influencers.
The old trade-off between financial returns and impact is dead. Today’s most successful investors are proving you can outperform the market while driving real, measurable change.
Join us for this exclusive, LP-only webinar, where you’ll gain insider knowledge on how to tap into hidden investment opportunities that deliver both exceptional returns and meaningful impact.
What You’ll Walk Away With:
🔥 The secret to identifying high-growth, high-impact investment opportunities in health, climate, and economic resilience
💡 Proven strategies for finding and funding private investments that generate top-tier returns
📈 Exclusive case studies of impact-driven investments that have outperformed traditional portfolios
🚀 Actionable deployment strategies to meet your dual mandate—without sacrificing financial upside
This isn’t just another webinar—it’s a game-changer for investors looking to future-proof their portfolios while making a lasting impact.
📅 Spots are limited—reserve yours now and gain a competitive edge in impact investing!
David Gritz is a leading authority on high-yield impact investing. As the co-founder of InsurTech NY and InsurTech Fund, he has helped incubate over 150 companies that have collectively raised $1B+ in capital—driving better health outcomes, faster disaster recovery, and economic growth. He also advises top insurers managing over $36 trillion on how to invest in ways that maximize financial returns while creating a more resilient world.
Upcoming Events & Programs
InsurTech NY events bring together carriers, brokers, startups, and investors to facilitate new relationships and share insights from insurance influencers.
Driving Growth and Transformation in Renewals & New Business
Key Details
AI in Insurance Webinar – Beyond Automation
Date: March 12th
Time: 12:00 pm (EDT)
Cost: Free
Watch the Webinar Recording Below
Artificial Intelligence is reshaping the insurance industry, but its potential extends far beyond workflow automation. In this exclusive webinar, Hyperexponential brings together industry experts to explore how insurers are leveraging AI to transform both renewals and new business strategies.
Who Should Attend: 📑 Underwriters | 📊 Actuaries | 🚀 Innovation Leaders
Our panel will discuss:
How AI-driven insights are helping insurers better understand risk profiles and streamline the renewal process.
The role of AI in expanding underwriting capabilities—enabling insurers to confidently write business they previously avoided.
Whether AI is merely automating processes or actively driving top-line growth and strategic expansion.
Risa Ryan is the Head of US P&C at Hyperexponential, where she leads analytics-driven initiatives in the insurance sector. With extensive experience in underwriting and data analysis, she previously served as Chief Underwriting Officer at Sompo International and held leadership roles at Swiss Re Corporate Solutions and QBE North America. She is also the founder of UnRetire, focusing on innovative approaches to career transitions.
Richard Gunn is the President and Chief Revenue Officer at Hyperexponential, leading the company’s U.S. expansion and driving revenue growth. With over a decade of experience in strategy, operations, and financial consulting, he previously worked as an independent consultant advising on corporate strategy and due diligence. His background includes leadership roles at Deloitte and Accenture, where he specialized in finance strategy and market analysis.
Head of North American Actuarial Advisory | Guy Carpenter
Brian Johnson is the Head of North American Actuarial Advisory at Guy Carpenter, where he leads strategic actuarial initiatives for insurers and reinsurers. With extensive expertise in risk analysis, pricing, and capital management, he plays a key role in shaping actuarial strategies across the industry.
InsurTech NY events bring together carriers, brokers, startups, and investors to facilitate new relationships and share insights from insurance influencers.
Welcome to one of our most impactful webinars yet, proudly sponsored by Indemn. If you missed it live, now’s your chance to catch up on the game-changing insights that had the industry talking.
Join our expert panel as we dive into the big question: Is AI the New Internet? Featuring Russell Findlay, former CMO of Hiscox (a trailblazer in digital insurance sales), and Kyle Geoghan, CEO of Indemn (pioneering AI-driven insurance agents), this conversation explores AI’s potential to reshape insurance just as the internet once did.
Will AI redefine how carriers sell and service policies?
Can it drive digital transformation faster than ever before?
Or is AI simply the next step in an inevitable evolution?
This was not just another AI webinar—it was a must-watch discussion on the future of the industry. Watch the full recording now and see for yourself.
Russ Findlay is a seasoned executive with over 20 years of leadership across global markets. He has led multiple marketing and sales teams, launched and repositioned brands, and driven significant growth through strategic leadership. His career highlights include serving as CMO for four companies and earning multiple awards for creative and leadership excellence.
Kyle Geoghan is the Co-Founder and CEO of Indemn, a pioneering conversational insurance platform that leverages AI to enhance sales and service workflows. With over a decade of experience in the insurance industry, he has held leadership roles at CoverWallet (an Aon company), where he managed Professional Lines and directed Insurance Operations. Kyle’s deep expertise in insurance and AI-driven innovation positions him as a thought leader in transforming how insurance services are delivered.
Checkk out our free webinar, hosted October 8th, 2024, where we dived into the evolving landscape of alternative risk and explore how captives are becoming a critical component for MGAs looking to de-risk and optimize their business models.
The Social Concept of Captives: Understand the role captives play in the modern insurance ecosystem and how they can be integrated into your MGA strategy from day one.
Adapting to a Changing Landscape: Explore how the alternative risk landscape is expected to shift over the next two years and what it means for MGAs.
Optimizing Programs for Underwriting Profit: Learn how to design and implement programs that capture underwriting profit in this evolving system.
Financial Housekeeping Essentials: Discover why having your financials in order is crucial, especially if you require fronting arrangements.
Who is this Webinar For?
MGAs looking to de-risk and optimize their operations
Insurance professionals interested in alternative risk solutions
Financial leaders who manage or plan to manage captive insurance programs
This session is relevant for both existing programs and new ones, providing actionable insights that can help you future-proof your MGA model. Don’t miss out on this opportunity to stay ahead of the curve and ensure your MGA is prepared for the future.
David Gritz is a renowned expert in the startup ecosystem, with years of experience guiding investors and entrepreneurs alike. His insights have shaped the strategies of countless professionals, making him a leading voice in the field.
Gabriel Weiss is the CEO & Co-Founder of XN Captive and a seasoned entrepreneur in the fintech and insurtech sectors. Previously, he co-founded Safekeep, serving as Chief Customer Officer before it was acquired by CCC Intelligent Solutions. With a deep focus on innovation and customer experience, Gabriel continues to drive industry advancements in his leadership role.
Join us on September 6th for an insightful 30-minute webinar with David Gritz, GP of InsurTech Fund. Open to accredited investors, this session will provide you with actionable knowledge on the venture capital process and how to excel in startup investing.
If you were ever interested in learning how VCs invest, you wont want to miss this webinar. David Gritz, GP of InsurTech Fund will go under the hood and share how anyone can follow his process to find deals, and do due diligence to invest in the best startups and get top decile performance like InsurTech Fund (+25% IRR).
What You’ll Learn:
VC Investment Process: Discover the essential steps VCs take to identify and assess promising startups.
Deal Sourcing: Learn proven strategies for finding high-potential investment opportunities.
Performance Metrics: Understand how to achieve top decile performance, as evidenced by InsurTech Fund’s +25% IRR.
Why Attend:
Expert Insights: Gain valuable knowledge from David Gritz, a leading expert in startup investing.
Free Access: Enjoy this high-quality content at no cost.
Networking Opportunities: Connect with industry professionals and fellow investors.
Webinar Host
David Gritz
David Gritz is a renowned expert in the startup ecosystem, with years of experience guiding investors and entrepreneurs alike. His insights have shaped the strategies of countless professionals, making him a leading voice in the field.
A… B… C… Do you know what marketing KPIs will convince a VC you’re ready to raise your next round?
Join a fascinating discussion between Andrea Collins and Marlena Sarunac as they share how to set up insurtech marketing, sales and revenue teams for success with the essential metrics that will impress potential investors and demonstrate your readiness to secure funding. Whether you’re aiming for Series A, B, or C, this event will equip you with the knowledge and insights you’ll need to set up your strategy for a marketing slam dunk. Don’t miss this opportunity to fine-tune your pitch and take your insurtech startup to the next level!
Questions we’ll cover:
→ What are the primary marketing KPIs investors look for at the Series A stage?
→ How does the marketing strategy evolve from Series A to Series B and beyond?
→ What advanced marketing KPIs are crucial for Series C fundraising?
→ How do you demonstrate market dominance and competitive advantage?
→ How do you scope and scale your marketing and content teams to meet the needs of your business, and when should you leverage vendor partners to fill in the gaps?
Join us for a virutal information session and Q&A on the Global InsurTech Startup Competition currently accepting applicants. Register here for the info session and you will be sent a calendar invite with link.
InsurTechNY’s mission is to bring together carriers, brokers, startups, and investors to help accelerate the digital transformation of the insurance industry in the greater New York region. Please visit our website, www.InsurTechNY.com for more details.
A Previous InsurTech NY Event
Below is an example of one of our regular education and networking events. Influencers from Carriers/Brokers such as Legal and General, Prudential, & Swiss Re and InsurTechs and Solution Providers such as Impira, Instabase, and Ushur shared valuable insights. We also have a wide range of institutional and angel investors attend our events.
Video: See our YouTube Channel for more recordings of our previous events.
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Embedded Insurance is expected to exceed $70B in GWP by 2030. It represents the future of distribution, promising to improve customer experience and margins for insurers.
However, most embedded insurance offerings today focus on non-complex lines of business, like mobile phone warranties or mobility products. For embedded insurance to reach its full potential, the right infrastructure and expertise are needed.
Join experts from Volvo Financial Services and InsureMo as they break down how to build a scalable embedded insurance system for complex lines of business, improving both risk selection and operational efficiency.
Who is the Webinar For?
Corporate IT: CIOs, VPs, Directors, and IT Managers
Analytics: VPs, Directors, and Managers in Analytics
Trenholm Palmer is the Director of Digital Insurance at Volvo Financial Services, leading commercial and connected insurance distribution for heavy trucks and construction equipment. With over 13 years in commercial insurance brokerage, consulting, and insurtech advisory, he has deep expertise in insurance innovation, distribution, and strategy. Previously, he founded New Light Research, providing alternative data insights to top financial and re/insurance firms. Trenholm holds a BA from Washington & Lee University and an MBA from ISM in Paris.
Chuck Gomez is the Head of North America Operations at InsureMO, bringing over 25 years of experience in insurance technology, operations, and distribution. He has led digital transformation initiatives for major insurers and MGAs, specializing in core systems, APIs, and embedded insurance solutions. A seasoned industry leader, Chuck drives innovation in insurance infrastructure, helping carriers and insurtechs scale efficiently.