Generative AI Advisory in Chicago.
Where to use AI — and where not to. Shipped by senior engineers in Chicago, async-first, fixed-price.
IRPR.io ships generative ai advisory work for Chicago teams — engineering-led, async-first, and senior-only. Where to use AI — and where not to.
Our strategy practice has delivered generative ai advisory projects across startups, scale-ups, and enterprise operators. Every engagement is fixed-price, fixed-scope, and ends with a production-grade handoff.
Chicago sits at the intersection of finance, logistics, and enterprise software. Home to Morningstar, Groupon, and a dense trading/fintech cluster, it's one of the most pragmatic, revenue-focused tech ecosystems in the country.
Types of generative ai advisory we ship for Chicago teams.
AI chatbot / copilot
Domain-grounded RAG chatbots with eval harnesses and cost controls.
AI agents
Tool-using agents for outbound, research, and document work.
Document intelligence
Contract, invoice, and claims extraction with vision + structured outputs.
AI-powered search
Semantic search with reranking, 2-4x CTR lift on real query logs.
LLM integration
GPT, Claude, Gemini, and open-source model integrations.
Custom ML models
Fine-tuned and custom ML for classification, prediction, and scoring.
Generative AI Advisory for every Chicago business.
Search terms people type, matched to products we've built. Nothing on this list is hypothetical — every category here has shipped code.
AI by vertical
AI chatbots and copilots
AI automations
AI products
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Industries we build generative ai advisory for in Chicago.
Why Chicago is a tech city.
Chicago sits at the intersection of finance, logistics, and enterprise software. Home to Morningstar, Groupon, and a dense trading/fintech cluster, it's one of the most pragmatic, revenue-focused tech ecosystems in the country.
Generative AI Advisory that ships - on Chicago's terms.
Chicago-aware engineering
We know the fintech and logistics buyers in Chicago. Our roadmaps reflect what local operators actually ship.
Senior-only delivery
Every generative ai advisory project is led by an engineer who has shipped this work in production. No junior delegation.
Fixed price, fixed scope
You know the budget and timeline before engineering starts. Change orders are priced transparently.
US-aligned async-first
We overlap Chicago work hours for standups, demos, and decisions. No overnight timezone drag.
Compliance by design
HIPAA, SOC 2, PCI, GDPR - baked in at architecture, not bolted on for audit. We've passed first-attempt audits for clients in your industry.
Your code, your IP
Every repo, piece of infrastructure, and document is handed off on day one. No proprietary frameworks, no lock-in.
Idea → Roadmap → Product → Release.
Every engagement runs through the same four-stage pipeline. Predictable by design.
More from Chicago.
Other services we ship in Chicago, and the same generative ai advisory expertise in other US metros.
Other strategy work we ship in Chicago.
Questions clients ask first.
Your generative ai advisory project in Chicago, shipped.
Book a discovery call with an engineer who has shipped generative ai advisory projects for Chicago teams. 30 minutes, no deck.