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Technical AI Lead, Document Generation, Administration

November 3, 2026

Job Description:

Lead AI initiatives end to end, from business discovery and solution design through prototyping, architecture, integration, evaluation, implementation, rollout, adoption, and continuous improvement
Identify and frame high-value AI opportunities with business stakeholders
Determine whether generative AI, agentic automation, document intelligence, traditional automation, or process redesign is appropriate
Define scalable AI solution architectures connecting LLMs, AI agents, RAG, enterprise data, Salesforce, APIs, document platforms, workflow orchestration, and other enterprise systems
Design agentic AI workflows that retrieve enterprise information, reason over business context, invoke tools and APIs, and execute multi-step processes with human oversight, controls, and guardrails
Establish enterprise RAG and knowledge architecture patterns for document ingestion, metadata, embeddings, vector and hybrid search, grounding, citations, access-controlled retrieval, and retrieval evaluation
Lead document intelligence solutions for lease abstraction, contract analysis, clause identification, obligation extraction, risk analysis, document classification, document generation, and related Leasing and Legal workflows
Provide technical direction and coordinate delivery across engineers, architects, vendors, and onshore/offshore teams
Establish engineering standards, conduct architecture and design reviews, resolve complex technical challenges, and align stakeholders on dependencies, risks, data readiness, timelines, and adoption

Requirements:

7+ years of experience in technical leadership, software engineering, enterprise architecture, AI delivery, CRM, data platforms, digital transformation, or closely related enterprise technology disciplines
Experience designing and delivering generative AI solutions incorporating LLMs, agentic workflows, RAG, enterprise search, document intelligence, prompt engineering, or workflow orchestration
Ability to prototype, evaluate, and troubleshoot AI solutions using Node, Python, SQL, APIs, JSON, enterprise AI platforms, and modern AI development tools
Experience designing agentic workflows incorporating enterprise retrieval, reasoning, tool or API execution, orchestration, state management, human oversight, guardrails, and evaluation
Experience evaluating AI accuracy, groundedness, hallucination risk, retrieval quality, extraction performance, agent or tool execution, and end-to-end workflow success
Experience applying AI to complex unstructured content, including leases, contracts, legal documents, or other enterprise documents
Experience with complex Salesforce or CRM environments and related data, integrations, workflows, automation, reporting, or AI capabilities
Experience integrating structured and unstructured enterprise data through APIs, middleware, ETL/ELT, data pipelines, and data platforms such as Snowflake or comparable technologies
Experience moving AI solutions from prototypes into production, including testing, deployment, monitoring, governance, support, and continuous improvement
Ability to translate complex business processes and evolving requirements into executable technical solutions and communicate architecture and AI concepts effectively to business and technical stakeholders
Preferred: Experience in logistics real estate, commercial real estate, leasing, legal operations, contract management, document generation, or adjacent B2B business processes
Preferred: Experience with CLM, document generation, eSignature, contract analytics, legal AI, or comparable document-centric enterprise platforms
Preferred: Experience with Dataiku, Snowflake, Salesforce AI capabilities, OpenAI or comparable LLM platforms, vector databases, and enterprise integration technologies
Preferred: Experience with Git, CI/CD, automated testing, API development, developer tooling, and cloud-based application architectures
Preferred: Experience providing technical leadership across internal teams, vendors, and globally distributed onshore/offshore engineering teams
Demonstrated willingness and capability to leverage emerging technology, automation, and AI tools
All job offers are contingent upon successful completion of background verification

Benefits:

Healthcare, dental, and vision insurance for employees and eligible dependents
401(k) retirement plan with a company match of 50% up to 12% of eligible compensation
Generous PTO with a starting accrual of 22 days a year
Paid holidays
Volunteer time
Wellness, financial, and work/lifestyle-specific benefits
Quality management and leadership development
Background verification for job offers

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...