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The Company

Chosen Local — AI Operations for Claims Contractors,
Built From the Inside Out

Most tech companies try to learn the claims industry. We already know it — 7 years in roofing and restoration contracting, now building claims contractor AI automation and Xactimate supplement automation from Milwaukee, WI.

Jack Leszczynski — Founder & CEO of Chosen Local
Jack Leszczynski
Founder & CEO · Chosen Local
Milwaukee, WI
Credentials
🎓
AI-Powered Platform, Built for This Industry
The tech was built to serve the business need — not the other way around
🏗️
7 Years in the Claims Industry
Xactimate, O&P, RCV vs. ACV, AOB, adjuster negotiation — fluent, not learned
📍
Based in Milwaukee, WI
Serving claims contractors across the United States
🛠️
Managed Service — Not Software
Our team maintains everything. You get outcomes, not a vendor relationship
Jack Leszczynski — Founder and CEO of Chosen Local, claims industry AI expert based in Milwaukee WI
Jack Leszczynski
Founder & CEO · Chosen Local

7 years inside claims contracting.
Built to help contractors win.

Jack spent 7 years on the operations side of claims contracting — close enough to see exactly where money disappears and why. Chosen Local is the platform he would have wanted if he owned a claims contracting company: AI doing the work carriers count on you not doing.

🏗️ Built From Inside the Industry
🏗️ 7 Years in Claims Industry
📍 Milwaukee, WI
🤖 AI & Claims Expert
Book a Call with Jack → See the Platform
"

"I've spent 7 years in claims contracting watching operators lose money every single day to problems that are completely solvable. Supplements not written on every job. Holdbacks that never get collected. Calls missed during storms. File chaos that kills deals.

I could see what AI was going to do for this industry, and I knew the only way to build it right was to build it from the inside — not from a product roadmap, but from 7 years of watching exactly where claims contractors lose.

Chosen Local is the complete claims contractor AI automation system I would have wanted — AI voice agent, Xactimate supplement automation, financial dashboards, and more. Built for owners who are done leaving money on the table. Not a generic automation tool with a roofing skin on it. Something built by someone who actually knows the difference between an ACV check and a holdback release — and knows why that matters at 11pm on a Tuesday."

AI Operations for Claims Contractors —
Managed Service, Not Software

The managed service model exists because software that requires your team to operate it isn't solving the problem — it's shifting work. Our job is to handle the operations side of your business so you don't have to think about it.

That means when something breaks, we fix it. When a carrier changes their supplement guidelines, we update our system. When a new automation is available, you get it — without a new project or a new invoice.

Industry-first design
Every feature was built because we saw exactly how contractors were losing money — not because it looked good in a pitch deck.
No babysitting required
We deploy, we maintain, we update. Your team uses the outputs — they don't manage the system.
Paid for by the value it creates
The platform pays for itself in week one from supplement recoveries and missed calls captured alone.

Why Industry-Specific AI Outperforms
Generic Software Every Time

The Problem with Generic Business Software for Claims Contractors

The claims contracting industry has a technology adoption problem that every contractor feels but few can articulate precisely. Generic CRM platforms like Salesforce, HubSpot, and even contractor-specific tools like JobNimbus and AccuLynx were built around workflows that do not match how insurance-driven contracting actually operates. They track leads and jobs in ways that make sense for retail service businesses but fail to capture the critical variables that determine profitability in claims work — ACV versus RCV payment status, supplement approval tracking, holdback collection timing, carrier-specific compliance requirements, and the specific document workflow that insurance claims demand.

The result is that claims contractors spend thousands of dollars on software that was not built for them and then spend thousands more hours working around its limitations. Supplement tracking happens in spreadsheets. Holdback balances live in someone's memory. Carrier follow-up falls through the cracks because there is no automated system that understands the specific timing and documentation requirements of insurance claim resolution. Document chaos accumulates because generic file storage has no understanding of what an AOB is, why a COC matters, or when a moisture log is missing.

Chosen Local was built specifically to solve this problem. Every data model, every automation, every dashboard, and every integration was designed around the actual workflow of a claims contracting business — not the workflow of a generic service company with a roofing skin applied on top.

What "Managed Service" Means — and Why It Matters

Most business software is sold as a self-service tool. The contractor pays a monthly subscription, attends an onboarding call, and then figures out the rest themselves. They configure automations that half-work, maintain integrations that break when APIs update, and eventually stop using the features that require ongoing maintenance because they do not have time. The software becomes expensive infrastructure that the business depends on but barely uses to its potential.

Chosen Local operates as a managed service. The Chosen Local team deploys the platform, configures every automation, connects every integration, writes the voice agent script, tests every workflow, and monitors performance after launch. When the weather API changes its response format, we fix the integration. When Twilio updates its SMS pricing structure, we adjust the configuration. When a new carrier begins requiring a different document format, we update the document classification model. The contractor never troubleshoots their own AI.

This managed approach means the platform works at a higher level than any self-configured tool can achieve. It also means the contractor never has to build technical expertise they did not want — they can remain focused entirely on running their contracting business while the platform handles the operational infrastructure.

The Claims Contractor AI Automation Technology Stack

The Chosen Local platform is built on a technology stack chosen specifically for the demands of insurance-driven contracting operations. The AI voice agent runs on enterprise voice infrastructure with sub-second response latency, capable of handling concurrent calls during storm surge events. Document processing uses optical character recognition tuned specifically for insurance estimate PDFs — which have distinctive formatting that generic OCR tools struggle with. The financial dashboard connects to QuickBooks Online via their official API with read-only access, meaning the contractor's accounting data is never at risk from a third-party write operation.

AI-generated content — the monthly P&L narrative, the supplement drafting assistance, the document classification system — uses Claude, Anthropic's flagship AI model, which has demonstrated superior performance on structured document analysis and professional business writing tasks. Weather data comes from Tomorrow.io, which provides hyperlocal hail size and wind speed data at the specific address level needed for accurate job scheduling impact assessment. Workflow automation runs on Make.com and n8n, providing the reliability and monitoring needed for business-critical processes.

Every component of the stack was chosen for reliability, accuracy, and fit to the specific task — not for cost minimization or convenience. Claims contractors depend on this infrastructure for their livelihood; it has to work correctly the first time, every time.

Frequently Asked Questions — About Chosen Local

Who is Chosen Local built for?

Chosen Local is built for claims contracting businesses — roofing contractors, water and fire restoration companies, mold remediation businesses, and public adjusters — who run a significant portion of their revenue through insurance claims. The platform is specifically designed for the insurance-driven contracting workflow and is not suited for contractors who work exclusively outside of insurance claims.

How is Chosen Local different from JobNimbus or AccuLynx?

JobNimbus and AccuLynx are CRM and project management platforms. Chosen Local is an AI operations platform — it automates the work that happens around jobs: answering phones, writing supplements, tracking carrier payments, managing documents, and communicating with homeowners and carriers. Chosen Local is designed to work alongside the contractor's existing CRM, not replace it. Our abstraction layer connects to JobNimbus, AccuLynx, or the contractor's own system and adds the AI automation layer on top.

What size contracting business is a good fit?

Chosen Local is designed for small to mid-sized claims contracting businesses — typically 2 to 50 employees, running anywhere from 20 to 500 insurance claims jobs per year (based on Chosen Local client profile data). The platform delivers the highest ROI for businesses that are currently losing money to missed calls, uncollected holdbacks, unsupplemented jobs, and manual admin overhead. Very large enterprises with dedicated operations teams may be better suited to enterprise-specific software; very small operations doing fewer than 20 claims jobs per year may not generate sufficient volume to justify the platform investment.

Is Chosen Local affiliated with Xactimate or CoreLogic?

No. Chosen Local is an independent company with no affiliation with Xactimate, CoreLogic, Verisk, or any insurance carrier. Our supplement writing service uses Xactimate as the industry-standard estimating platform, and our specialists are trained in Xactimate methodology — but Chosen Local is not endorsed by or affiliated with Xactimate or its parent companies.

How does Chosen Local handle contractor data privacy?

Contractor data is never sold, shared with third parties for advertising, or used to train AI models without explicit consent. QuickBooks access is read-only — Chosen Local never writes to a contractor's accounting records. All data is encrypted in transit and at rest. Chosen Local operates under a service agreement that includes data ownership provisions confirming that the contractor retains ownership of all their business data at all times.

Talk to the Claims Industry Expert
Who Built the Platform

Book a 30-minute call. Jack walks every demo personally — no sales reps, no scripts. You'll get straight answers about what the platform can do for your specific business.

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Sources & Data Notes

Chosen Local client profile data. Business size and claims volume ranges based on active platform clients. 2024–2025.

Internal data note: Statistics labeled "Chosen Local data" or "Chosen Local analysis" are based on Chosen Local's observations across client engagements and supplement service submissions and are not independently verified by a third party. Statistics labeled "industry estimate" reflect commonly cited figures in the roofing and insurance claims industry without a single definitive primary source.