Context Windows

Real Estate

AIProductLead

$200–230k Chicago, Illinois, United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Lead candidates.

The Brief

“AI Product Lead at Context Windows. Skills: AI Solutions, LLM Development, System Integration, Product Management. Design and build AI-powered solutions. Build AI layer: logic, context, pipelines, integrations”

Industry & Context.

Real Estate
Problems you'll solve

Iterate based on failure modes; Decompose real-world workflows into problems AI can solve reliably

Eligibility Requirements

This position does not provide visa sponsorship, Candidates must be authorized to work in the United States without sponsorship

What They're Looking For.

Must Have

Authorized to work in the United States without sponsorship

Nice to Have

Familiarity with Python: file I/O, data parsing, scripting for automation, Familiarity with REST APIs and enterprise integration patterns, Comfort with version control (Git), structured file management, and markdown-based documentation, Exposure to enterprise security and governance requirements for AI systems (data residency, access controls, audit logging), Hands-on experience building with large language models: designing system prompts, managing context, structuring inputs and outputs, optimizing for token efficiency, handling failure cases, Understanding of how context design affects LLM output quality and reliability, Familiarity with retrieval-augmented generation (RAG) concepts, Exposure to agentic patterns, tool use, and multi-step AI reasoning, Curiosity about emerging AI infrastructure patterns (orchestration frameworks, context protocols, model APIs), Experience working in or familiarity with the construction, commercial real estate, or professional services industry, Experience in a product management, engineering, data science, or other relevant technical role, You build things outside of work because you find the problems interesting, You follow AI model and tooling developments because you want to, not because someone asked you to, You're comfortable in problem spaces where the best practices are still being written, and you find that energizing, When the technology shifts, you shift with it

What You'll Do.

Design and build AI-powered solutions

Build AI layer: logic

Design AI-powered workflow tools

and maintain AI solutions

Write supporting code: scripts for parsing

Connect AI tools to enterprise environment

Decompose workflows into AI solvable problems

Design AI inputs and outputs

Write instructions for consistent results

Develop intuition for AI performance and guardrails

Run solutions against diverse documents

Define 'good' output quality

Work with project managers to understand workflows

Translate processes into specifications

Communicate AI capabilities and limitations

How You'll Work.

Team & Collaboration

Work directly with PDS project managers; Communicate clearly about AI capabilities

Communication Scope

Communicate clearly about what AI can and cannot do reliably

Full Job Description

**JLL empowers you to shape a brighter way**. Our people at JLL are shaping the future of real estate for a better world by combining world class services, advisory and technology for our clients. We are committed to hiring the best, most talented people and empowering them to thrive, grow meaningful careers and to find a place where they belong. Whether you’ve got deep experience in commercial real estate, skilled trades or technology, or you’re looking to apply your relevant experience to a new industry, join our team as we help shape a brighter way forward. **ABOUT THE ROLE** JLL's Project & Development Services (PDS) organization is deploying AI across its construction and real estate project delivery workflows, and we're looking for someone who builds things because they can't help themselves. You stay current on AI not because it's your job but because you find it genuinely fascinating. You have side projects. You've broken things trying to understand how they work. You have opinions about context windows. In this role you'll design and build AI-powered solutions that PDS project managers use on a daily basis. You won't be building large standalone applications. You'll be building the AI layer: the logic, the context, the pipelines, and the integrations that make a general-purpose AI model behave like a domain expert in construction project delivery. The specific form that takes will evolve as the technology evolves, and you'll be expected to evolve with it. **WHAT THIS JOB INVOLVES** **Designing and Building AI Solutions** \- Your primary output will be AI-powered workflow tools: structured, versioned, documented solutions that guide an AI model through specific PDS tasks like reviewing a GC payment application, abstracting a commercial lease, or analyzing a construction schedule for risk. These are not one-off prompts. They have defined inputs, structured outputs, behavioral guardrails, and quality checks. You'll build them, test them against real documents,

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