Insurance Is a Laggard Industry. You Can Get an Amazon Package Faster Than a Quote.

Jon Corrin’s first startup was a college carpooling app — a BlaBlaCar for the US, built with a childhood friend who was a Naval Academy student. It grew to a few thousand downloads and a few hundand active users, monetizing nothing because, as Jon put it, they didn’t know what they were doing. Then his co-founder and CTO got deployed after graduation, the app crashed, and Jon — with no iOS development knowledge, no money for a contractor, and no idea how to raise capital — watched it die with no way to save it.

That failure is what actually made him a software engineer. He taught himself to code, landed at Parallel 6, a San Diego company building enterprise forms for clinical research organizations working with clients like GlaxoSmithKline, and worked his way from customer success into engineering. Years later, a different childhood friend — whose father had built a non-standard auto agency from nothing in the early 1990s, and who himself started as a 13-year-old answering agency phones before becoming VP of Sales by his twenties — became Jon’s co-founder at XILO, bringing the insurance domain expertise Jon didn’t have.

In Episode 121 of InsurTechTalk, Jon and I covered why most agencies still run zero real automation despite a decade of industry talk about it, the staffing crisis hiding behind the retiring-agent narrative, and the delicate three-way balance between sales, product, and customer success that almost broke his company in its first two years.

About Jon Corrin

Jon Corrin is the co-founder and CEO of XILO, a workflow automation and customer experience platform built for insurance agents — brokerages, bank and credit union insurance arms, and increasingly organizations outside traditional insurance that manage risk at scale. XILO’s customer base spans startup agencies through top-100 P&C brokerages. Before founding XILO, Jon was a self-taught software engineer at Parallel 6, building enterprise form and workflow solutions for clinical research organizations.

A Decade of “We Need Automation” and Still Almost None Exists

I’ve been in insurance about ten years and have heard the case for agency automation the entire time. Jon’s answer to why the problem persists was blunt: at the individual agent level, most organizations we talk to have no real automation implemented at all — even large brokerages and financial institutions. Most run some combination of an agency management system, maybe a comparative rater, maybe an emerging CRM (increasingly Salesforce) — but these remain disconnected systems that don’t actually tie workflow and customer engagement together into anything that reduces task time.

The Staffing Crisis Behind the Retirement Wave

The generational handoff in insurance distribution — veteran agents retiring, new licensees replacing them — gets discussed constantly as a knowledge-transfer problem. Jon’s customers describe it more starkly, as a staffing math problem: how do you get one new hire, whose early success rate will likely be low, to do the work of the two, three, or four veteran producers they’re replacing?

His view is unambiguous: without AI, that math doesn’t close. Software alone might lift productivity 10-40%. Getting to the 100-300% gains agencies actually need requires combining automation with AI, not either alone.

Data Intake Is Deceptively Hard

The customer experience gap XILO addresses starts somewhere that sounds almost trivially simple: data intake. Jon’s point is that intake looks simple in most industries and is genuinely complex in insurance — the process can differ substantially even between two agencies selling the same product from the same carrier in the same state. Solving that fragmentation is, in his framing, the actual prerequisite to solving the customer experience problem, not a separate initiative from it. XILO’s approach is a white-labelable customer experience layer paired with internal tooling that lets each agency customize intake to their specific carrier and product mix.

Who Actually Calls XILO

The customer profile splits cleanly by organizational maturity, and the reasons differ:

• Startup and newly-independent agencies — captives going independent, fintechs opening insurance divisions — arrive wanting to look like Next Insurance, Lemonade, or GEICO Direct from day one: fully digital, fully automated. XILO doesn’t always take these on, because the product requires a high service touch to configure correctly
• Large brokerages, XILO’s primary customer base, are running processes largely unchanged for 10-15 years, and the pitch that lands with them is holistic rather than point-solution. Many have grown by acquiring Florida agencies, California agencies, Northeast agencies — each running different agency management systems, different comparative raters, different lines of business — and are trying to standardize hundreds of fragmented offices at once
• Banks and credit unions have become a surprisingly large growth segment over the prior 12 months — a “titanic” community of financial institutions with insurance arms Jon didn’t initially expect

International demand exists too — organizations in Germany and Australia reaching out through SEO, describing the same underlying problems — but XILO hasn’t expanded there because of regulatory complexity. Germany specifically layers insurance-specific transaction handling requirements on top of GDPR, requiring dedicated compliance work XILO hasn’t yet built.

A Concrete Win: 10x Online Conversion for a Non-Standard Auto Shop

Jon walked through a specific, unnamed customer case that illustrates the mechanics of what automation actually changes.

The starting problem: a well-known non-standard auto agency was getting heavy referral-driven call-in business. Referred customers would land on the website, see a phone number instead of a modern buying flow, and call — meaning the agency had to staff for high call volume rather than benefiting from any self-service conversion.

XILO’s build:

• Mapped the agency’s specific carrier relationships and product lines to build carrier-appropriate intake questionnaires
• Designed the flow to also attempt cross-sell — collecting the additional details needed to quote a life policy alongside the core non-standard auto request
• Fully integrated collected data directly into the agency’s existing systems, eliminating the need for a human to transcribe a phone conversation into the system afterward

The result: a 10x increase in online conversion, generating 500-600 leads a month from the website alone, while eliminating 5-600 phone conversations a month running 10-45 minutes each.

The second layer — a “client portal” — extends the automation past the quote itself. Once an agent finalizes a quote in a carrier system like Progressive, it flows back into XILO as a smart proposal the client can review, request changes to, accept, and upload supporting documents against, entirely without a phone call. XILO also automates the follow-up reminders most agencies, in Jon’s experience, simply don’t have the bandwidth to send on the personal lines side. The net effect: processing time per client dropped over 50%, and because personal lines carries recurring renewal revenue, the ROI compounds every year rather than being a one-time conversion lift.

Where Carrier Technology Still Caps the Ceiling

I asked directly whether carrier technology capability is the limiting factor for XILO. Jon’s answer: yes, structurally. XILO doesn’t offer bind-online functionality itself, and true instant-bind capability is realistically only available through a handful of top national carriers — most of whom reject a large share of business at the outset anyway. His framing: agents are already living within these carrier constraints regardless of XILO’s involvement, so the platform is built to optimize everything within the boundary of what carriers currently support, rather than waiting for carrier technology to catch up.

Private Equity’s Interest in Brokerage Roll-Ups

We discussed the growing PE interest in acquiring brokerages specifically — cash-flowing, book-of-business-driven, “old school” operations that PE firms believe they can improve through the right technology injection. Jon’s view is that XILO fits squarely into that thesis: a small piece of infrastructure by dollar volume, but structurally important to the distribution layer PE buyers are trying to modernize post-acquisition.

The Product-Sales-Customer Success Triangle

We discussed the classic time-quality-cost project triangle, and Jon offered a different one specific to running an early-stage company: the ongoing tension between sales, customer success, and product.

His description of the trap: spend six months building sales conversion and operations, and growth outpaces customer success capacity — forcing a rebuild of the support side. Fix that, and product falls behind what customers are asking for, which eventually erodes both sales and retention. His conclusion, arrived at through direct experience in XILO’s first two years: product quality and delivery speed are what make the other two easier, not a separate lever to balance against them — better and faster product releases directly drive both higher sales conversion and stronger retention.

His honest caveat: as an early-stage company, you can’t simply hire an experienced VP to solve this the way a larger company would — you have to earn the resources to do that through execution first.

Advice: Build the Security Culture Before You Need It

Asked for advice specific to someone entering insurtech, Jon’s answer was pointed rather than general: start with a highly secure system from day one, especially if you’re handling sensitive data — which most insurtech companies are.

His reasoning, learned through XILO’s own growth into larger enterprise customers: security maturity only reveals its importance once you’re selling to organizations that demand it, and retrofitting a security culture into an engineering team three, four, five years in costs far more — in both investment and lost time — than building it in from the start. His concrete recommendation: adopt a compliance tooling platform (naming Vanta and Drata as examples) early, and treat it as foundational rather than a later-stage checkbox.

Key Takeaways

• Despite a decade of industry conversation about automation, most agencies and brokerages — even large ones — have essentially no real workflow automation in place today
• The retiring-agent narrative is really a staffing math problem: replacing one veteran producer’s output requires AI-augmented tooling, not just a new hire and hope
• Data intake, which looks trivial in most industries, is genuinely complex in insurance and is the actual root of the customer experience gap, not a separate problem from it
• A single well-targeted automation project — carrier-mapped intake plus automated follow-up — produced a 10x online conversion increase and cut processing time per client by over half for one agency
• Carrier bind-online capability remains the structural ceiling on how far agent-side automation can go; the practical strategy is optimizing fully within that constraint rather than waiting on carriers to modernize
• Product quality and delivery speed are the actual lever that makes sales and customer success easier — not a third competing priority to trade off against them
• Build security and compliance culture into an engineering team from day one; retrofitting it after several years of growth costs significantly more in both time and investment