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Lead Software Engineer, Gen AI

Caterpillar · Chicago, IL · $128,470–$208,770 a year · Full time

Posted Oct 5, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you led engineers through a project using technology none of you had used before.

What they are checking: Whether a lead can guide a team through uncertainty while keeping quality and morale up.

Tell me about a code review where you pushed back on a design. How did it go?

What they are checking: Whether they raise the bar through reviews while keeping working relationships healthy.

What would you do

A business partner wants a Gen AI feature that you think a simple rules engine would handle better. What do you say?

What they are checking: Whether they choose the right tool for the problem rather than using AI for its own sake.

Your assistant is getting slow and costly as usage grows. Where do you look first?

What they are checking: Whether they can reason about token use, caching, model choice and latency tradeoffs.

About the work

Walk me through how you would build an AI assistant that answers dealer questions using Caterpillar's technical documents.

What they are checking: Whether they understand retrieval, chunking, grounding and evaluation for a real generative AI assistant.

How do you design an agent that calls tools safely, and how do you stop it from taking a bad action?

What they are checking: Whether they think about permissions, validation and human checkpoints when agents act on real systems.

Describe a CI/CD pipeline you built with GitHub Actions. What did it test and what did it block?

What they are checking: Whether they have built real pipelines with meaningful gates, not just copied a template.

How would you deploy a Gen AI service on AWS with CloudFormation so it can be rebuilt the same way in every environment?

What they are checking: Whether they practice infrastructure as code and understand repeatable, reviewable deployments.

How do you measure whether an LLM-based feature is getting better or worse after a change?

What they are checking: Whether they build evaluation sets and regression checks instead of judging output by feel.

How do you apply object-oriented design in Python so an AI codebase stays maintainable as it grows?

What they are checking: Whether they write structured, testable Python instead of fragile notebook-style code.

Practice this interview out loud.

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The full job description

As published by Caterpillar.

Career Area: Technology, Digital and Data Job Description: Your Work Shapes the World at Caterpillar Inc. When you join Caterpillar, you're joining a global team who cares not just about the work we do – but also about each other. We are the makers, problem solvers, and future world builders who are creating stronger, more sustainable communities. We don't just talk about progress and innovation here – we make it happen, with our customers, where we work and live. Together, we are building a better world, so we can all enjoy living in it. Cat Digital is the digital and technology arm of Caterpillar Inc., leveraging the latest technologies to build industry leading digital solutions for our customers and dealers. With over 1.5 million connected assets worldwide, our teams use data, technology, advanced analytics, telematics, and AI capabilities to help our customers build a better, more sustainable world. Job Summary: As a Lead Software Engineer you will work on Generative AI projects focused building assistants, agents, GenAI tooling and software. Join our innovative team and contribute to the development of cutting-edge AI solutions at Cat Digital. What You Will Do: • Develop and deploy Gen AI solutions utilizing Python and OOP principles. • Implement and manage CI/CD pipelines using GitHub Actions. • Deploy solutions on AWS using CloudFormation. • Work with frameworks such as LangChain, LangGraph, Semantic Kernel, and Crew.ai. • Apply knowledge of Large Language Models (LLMs) and Prompt Engineering concepts. • Develop and deploy services using FastAPI on AWS. • Collaborate with data scientists to refactor analytics solutions for production, ensuring scalability and efficiency. • Assist in the development of machine learning and AI pipelines using Apache Airflow. What You Will Have: • Software Development: Knowledge of software development tools and activities; ability to produce software products or systems in line with product requirements. • Software Development Life Cycle: Knowledge of software development life cycle; ability to use a structured methodology for delivering and managing new or enhanced software products to the marketplace. • Software Product Design/Architecture: Knowledge of software product design; ability to convert market requirements into the software product design. • Software Product Technical Knowledge: Knowledge of technical aspects of a software products; ability to design, configure and integrate technical aspects of software products. • Software Product Testing: Knowledge of software product testing; ability to design, plan, and execute testing strategies and tactics to ensure software product quality and adherence to stated requirements. Top Candidates Will Also Have: • As technical lead you will have the ability to manage larger and more complex projects. • Software development experience and solid working knowledge of OOP principles • Experience in designing and developing software applications in Python and/or GoLang • Experience with Python libraries such as FastAPI, LangGraph, and LangChain • Experience working with Git version control on medium to large teams • Exceptional communication skills with experience working on a cross functional team • Deploying software using GitHub Actions or similar • Experience with AWS components such as Sagemaker Studio, Lambda, API Gateway, and RDS • Technical writing skills Additional Details: • This position has the option to be based out of either our Chicago, IL; Peoria, IL; Broomfield, CO (Denver) or Irving, TX (Dallas) offices • Relocation Assistance is NOT available for this role What You Will Get: Working with a Fortune 100 leader, you can build your career on a global scale and take advantage of development opportunities with emerging technologies. We’ve created an inclusive environment for you to explore your passions, make an impact and do the work that really matters. Join Us. About Caterpillar Caterpillar Inc. is the world’s leading manufacturer of construction and mining equipment, off-highway diesel and natural gas engines, industrial gas turbines and diesel-electric locomotives. For nearly 100 years, we’ve been helping customers build a better, more sustainable world and are committed and contributing to a reduced-carbon future. Our innovative products and services, backed by our global dealer network, provide exceptional value that helps customers succeed. Summary Pay Range: $128,470.00 - $208,770.00 Compensation and benefits offered may vary depending on multiple individualized factors, job level, market location, job-related knowledge, skills, individual performance and experience. Please note that salary is only one component of total compensation at Caterpillar. Benefits: Subject to plan eligibility, terms, and guidelines. This is a summary list of benefits. • Medical, dental, and vision benefits* • Paid time off plan (Vacation, Holidays, Volunteer, etc.)* • 401(k) savings plans* • Health Savings Account (HSA)* • Flexible Spending Accounts (FSAs)* • Health Lifestyle Programs* • Employee Assistance Program* • Voluntary Benefits and Employee Discounts* • Career Development* • Incentive bonus* • Disability benefits • Life Insurance • Parental leave • Adoption benefits • Tuition Reimbursement * These benefits also apply to part-time employees Visa Sponsorship is not available for this position. Posting Dates: October 5, 2026 - October 12, 2026 Any offer of employment is conditioned upon the successful completion of a drug screen. Caterpillar is an Equal Opportunity Employer, Including Veterans and Individuals with Disabilities. Qualified applicants of any age are encouraged to apply. Not ready to apply? Join our Talent Community .

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