The Last Integration You’ll Ever Need to Make

Listeners of this show have heard Michael Lebor’s name repeatedly as an offhand shoutout from other guests — a well-connected figure known for making introductions and, according to more than one prior guest, an almost supernatural ability to get anyone to scan a QR code at a conference. This episode is his own turn in the chair.

Michael spent five years at AmTrust — the first three as Chief Marketing Officer, the last two as Global Head of Digital and Innovation — before leaving to found InsuranceGIG, now roughly 15 people. He describes the transition as a deliberate, carefully discussed choice made with AmTrust’s leadership, who supported it rather than opposed it. AmTrust, a global company with roughly 10,000 employees at the time, gave him real scale and resources, but also — inevitably, in his account — real institutional speed limits. What ultimately pushed him out wasn’t dissatisfaction with the carrier; it was a specific, repeated frustration with how insurance technology actually gets bought.

In Episode 65 of InsurTechTalk, Michael and I covered why he thinks insurance’s biggest technology adoption problem is procurement, not innovation, how InsuranceGIG functions as an app store for insurance microservices, and why he insists InsuranceGIG’s model displaces no one — not agents, not underwriters, not vendors.

About Michael Lebor

Michael Lebor is founder and CEO of InsuranceGIG, a marketplace connecting insurance technology vendors (“creators”) with buyers (carriers, MGAs, wholesalers, and agents) through a shared, pre-built integration layer — often described by others, in his words, as “Zapier for insurance technology.” Before founding InsuranceGIG in July 2021, Michael spent five years at AmTrust, first as Chief Marketing Officer and then as Global Head of Digital and Innovation, following an earlier career in digital and e-commerce outside insurance.

A Culture of Failure, or the Lack of One

Asked what specifically drove him to leave a senior role at a large, successful carrier, Michael pointed first to a structural cultural problem he saw across large insurance organizations, not specific to AmTrust: an almost complete absence of tolerance for failure. In his framing, nobody at a large carrier or wholesale MGA wants to be the person associated with a failed vendor purchase, algorithm pilot, or new initiative — creating strong incentives to avoid trying anything until success is close to guaranteed. He contrasted that directly with his earlier career in digital and e-commerce, where a 2% conversion rate on a new campaign made someone a “rock star,” not a failure — a completely different relationship to acceptable risk than what he encountered inside insurance. His stated goal in founding InsuranceGIG was to make failure genuinely cheap, fast, and low-stakes, so people could actually experiment — his phrase for it: “ready, fire, aim.”

The Procurement Problem That Actually Pushed Him Out

The more specific, immediate frustration: as the person responsible for staying current on insurance technology across AmTrust’s entire supply chain, Michael regularly found vendors offering a genuinely excellent, narrow capability he wanted to consume directly — but buying even a single API-driven microservice routinely required 12 to 18 months of legal, governance, compliance, onboarding, and integration work, often at a cost running into six figures, regardless of how small or well-defined the actual service was. That friction wasn’t specific to AmTrust; he came to see it as structural across large insurance enterprises broadly. Recognizing that building a genuinely better insurance technology procurement process wasn’t something a carrier focused on underwriting workers’ comp and small commercial P&C risk should try to build internally, he discussed the opportunity candidly with AmTrust’s leadership and left, with their support, to build it himself.

InsuranceGIG: An App Store for Insurance Technology

Michael’s core sound bite for InsuranceGIG: an app store specifically for insurance technology, or a microservice marketplace — people frequently describe it back to him as “Zapier for insurance technology,” a comparison he’s comfortable with at a high level.

His diagnosis of the deeper friction underneath slow insurance tech buying isn’t just cost — it’s decision complexity. His illustrative analogy: imagine if signing up for Uber required prepaying a $15,000 credit balance upfront before taking a single ride. Virtually no one would sign up under those terms — yet that’s structurally close to how most insurance technology gets sold today, outside of genuinely massive investments like core policy systems. Worse, the purchase decision for a given piece of technology is rarely made by one person; it typically has to run a gauntlet of stakeholders across departments (claims, underwriting, the relevant business unit), each needing to be independently educated and persuaded — turning what should be a fast technical decision into what Michael called “a decision by democracy.”

The Translation Layer: Integrate Once, Access Everything

InsuranceGIG’s core mechanism is what Michael calls a translation layer: InsuranceGIG builds the integration to a given vendor or data source once, then makes that integration available to every buyer on its platform, rather than each buyer independently rebuilding the same connection. The idea traces directly back to something he observed at AmTrust: hundreds of partners integrating with AmTrust’s rate-quote-bind-issue API were, in large part, rebuilding functionally identical integration work over and over, a genuinely inefficient duplication of effort across the whole ecosystem.

His concrete example: Relativity6, a data vendor providing workers’ comp classification codes. InsuranceGIG integrated with Relativity6 once, and now any small agent on the InsuranceGIG platform has access to that same capability without building their own connection. Michael’s pitch, distilled into another of his sound bites: for anyone who integrates with InsuranceGIG, it’s designed to be the last integration they’ll ever need to make.

Not Disruption. Enablement.

Michael was explicit and repeated on this point: InsuranceGIG doesn’t aim to disintermediate anyone — not agents, not underwriters, not the vendors it partners with. Early in his own carrier career, tasked with building a direct-to-consumer initiative, he held the common assumption that technology would eventually displace agents entirely. Years later, his view had genuinely shifted: the more durable path to success is giving agents better tools, not replacing them. He offered a personal, slightly self-deprecating anecdote as evidence — when it came time to buy insurance for InsuranceGIG itself, despite being deeply immersed in digital-first insurance technology, he called a broker and worked the purchase through entirely by phone, without touching a single digital quoting tool. His broader point: direct-to-consumer distribution has a genuine place, but for middle-market and more complex risk, human brokers still add real value that digital-only channels haven’t replaced.

Why Small Agents Get “Whale Hunted” Out of Vendor Attention

Michael connected the slow, expensive enterprise procurement cycle directly to a related, less obvious consequence: because closing a single large enterprise deal can take 18 months, technology vendors are economically forced to focus almost exclusively on the largest possible buyers (“whale hunting”) who can justify that sales cost — leaving small agents, wholesalers, and MGAs with comparatively little vendor attention or access to genuinely useful technology. By aggregating demand into a shared marketplace, InsuranceGIG opens that same vendor technology up to a much longer tail of smaller buyers who were previously priced out of the conversation entirely.

The Apple App Store Analogy

Michael was clear that InsuranceGIG is deliberately agnostic across insurance verticals — not focused specifically on commercial or personal lines, not focused specifically on distribution or claims. His comparison: Apple’s App Store hosts Uber, Waze, Robinhood, Candy Crush, and Wordle side by side without picking a lane, because Apple built the underlying tooling and distribution rails, not the specific apps themselves. InsuranceGIG applies the same model to insurance technology specifically — building the shared infrastructure that lets any relevant insurance microservice reach any relevant buyer.

How a Buyer Relationship Actually Starts

Michael described InsuranceGIG’s actual sales conversation as deliberately need-first rather than product-first: asking a prospective buyer directly what their internal IT team has told them they either can’t or won’t build. His illustrative examples: a large wholesaler manually re-keying thousands of ACORD forms forwarded daily by agents; a submission workflow needing real-time business classification when an applicant (his example: “Tony’s Pizza Shop”) doesn’t know its own workers’ comp class code; or a need for digital certificates of insurance. InsuranceGIG then either connects that buyer to an existing marketplace partner or builds the needed integration directly — with no upfront payment, no exclusivity requirement, and no long-term lock-in contract. Michael’s underlying philosophy: value has to be delivered continuously to earn continued use, and any buyer unhappy with a given service on the platform should be free to simply try something else.

Everyone Has a “Superpower” — Stick to Yours

One of Michael’s sharper framings: every company in this ecosystem has a specific core strength — a carrier’s superpower is underwriting; a data vendor’s superpower is sourcing and querying the specific data relevant to its niche — and companies frequently waste resources building unrelated capabilities from scratch instead of focusing on what they’re actually best at. His pointed example: a specific insurance data vendor that had started building its own internal marketing automation platform because customers said the raw data alone wasn’t enough without a way to act on it — when that marketing automation capability was already available as an off-the-shelf microservice (his example: HubSpot) that could simply be integrated rather than rebuilt. InsuranceGIG’s role, in this framing, is exposing each partner’s actual superpower via a shared integration layer, so vendors can focus on what they do best rather than building adjacent infrastructure that already exists elsewhere.

Zapier, Applied to Insurance-Specific Workflows

Asked to explain the Zapier comparison more concretely, Michael described Zapier’s core mechanic — building “if this, then that” logic chains across otherwise disconnected digital tools — and explained that InsuranceGIG applies the same underlying idea specifically to insurance microservices. Because InsuranceGIG has already mapped authentication and data formats across every partner on its marketplace, it can chain multiple vendors’ services together into a single repeatable, scalable workflow: call vendor one, then vendor two, then vendor three, then combine and act on the responses together — something Michael argued has essentially never existed in insurance before, given how genuinely rare it is for even two or three separate vendor companies to coordinate a joint integration project together at all.

Competing With — or Complementing — Closed Ecosystems

Asked how InsuranceGIG relates to core system vendors like Guidewire and Majesco building their own vendor marketplaces and plugin ecosystems, Michael was direct that he doesn’t see genuine competition, even with real overlap in some areas — his broader philosophy is that there’s enough value to create and distribute across the ecosystem that direct competition rarely makes sense. His specific critique of vendor-run marketplaces: they’re deliberately scoped to serve only that vendor’s own existing customer base (a core policy admin system’s marketplace, for instance, generally only serves carriers already on that specific system) — a reasonable strategy for that vendor, but structurally different from what InsuranceGIG is building, which is meant to be genuinely open regardless of which policy admin system, AMS, or other underlying infrastructure a buyer already runs. His pitch to those closed-ecosystem operators: bring the vendors you’ve already integrated onto InsuranceGIG’s open marketplace, and InsuranceGIG will make its own integrated partners available within your ecosystem in return — mutual value rather than a turf war.

A Disruption Award at InsurTech Hartford

Michael recounted a recent pitch night at InsurTech Hartford, where InsuranceGIG won a disruption-focused award, voted on partly by the audience and partly by an insurance-savvy judging panel — a genuinely meaningful result to him given the difficulty of conveying what InsuranceGIG actually does in a compressed seven-minute pitch to roughly 100 people. Consistent with his broader philosophy, he was quick to credit other companies presenting that day, framing them as prospective future InsuranceGIG partners rather than competitors — describing his ambition as being “the rising tide that lifts all those ships.”

Advice: Thinking, Fast and Slow

Asked for a closing recommendation, Michael pointed to Thinking, Fast and Slow by Daniel Kahneman — not, in his words, a beach read, but the closest experience he’s had in his life to taking the red pill in The Matrix: a genuinely paradigm-shifting book that changed how he thinks about decision-making itself.

Key Takeaways

• Michael’s core frustration with large-carrier insurance technology procurement wasn’t a lack of good vendors — it was 12-18 month buying cycles and six-figure minimum commitments for even narrowly scoped, API-driven services
• InsuranceGIG functions as a shared integration layer: it builds the connection to a given vendor once, then makes that same integration available to every buyer on the platform, aiming to be “the last integration” any given buyer needs to make
• The platform is deliberately agnostic across insurance verticals — modeled directly on Apple’s App Store hosting unrelated apps side by side — rather than specializing in one line of business or one part of the insurance value chain
• InsuranceGIG explicitly positions itself as additive rather than disruptive: it doesn’t aim to disintermediate agents, underwriters, or the vendors it partners with, and instead targets the long tail of smaller agents and wholesalers that vendors’ enterprise-focused sales motions structurally neglect
• No upfront payment, no exclusivity, and no long-term lock-in are core to the buyer relationship, reflecting Michael’s belief that value has to be delivered continuously to retain a customer, not secured through a binding contract
• Michael frames InsuranceGIG’s relationship to closed, vendor-run marketplaces (from core system providers like Guidewire and Majesco) as potentially complementary rather than competitive, pitching a mutual integration-sharing arrangement rather than treating them as rivals
• His emphasis on companies focusing on their specific “superpower” rather than rebuilding adjacent capabilities from scratch — illustrated by a data vendor that tried to build its own marketing automation platform instead of integrating an existing one — is a recurring lens for evaluating where a shared marketplace like InsuranceGIG adds the most value