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Manager; AI Engineering

Caterpillar · Chicago, IL · $147,760–$240,110 a year · Full time

Posted Sep 30, 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 had to rebuild a team's delivery process because releases kept slipping.

What they are checking: Whether they diagnose root causes in how work flows rather than just pushing people to work harder.

How do you hire and grow engineers in a field where the tools change every few months?

What they are checking: Whether they hire for fundamentals and learning ability rather than chasing a specific framework.

What would you do

Your AI assistant gives a wrong answer about equipment safety to a customer. Walk me through your response.

What they are checking: Seriousness about incidents involving heavy machinery, plus a clear process for containment, fix and prevention.

A senior engineer on your team strongly disagrees with your technical direction. How do you handle it?

What they are checking: Whether they can lead with authority while still listening and changing course when the engineer is right.

How do you work with product managers when they want more features and your team needs time for reliability work?

What they are checking: Ability to negotiate priorities and make reliability work visible in terms the business cares about.

About the work

Walk me through the architecture of a cloud-native AI agent you've built or overseen, from user request to response.

What they are checking: Real depth in how agents, retrieval, tools and cloud services fit together, not just buzzword familiarity.

How do you take an AI assistant from prototype to something enterprise-scale for customers, dealers and employees?

What they are checking: Whether they know what production requires, like monitoring, cost control, security and fallback behavior.

How do you decide what your team should build in-house versus use from a model provider or platform?

What they are checking: Judgment about where custom work adds value and where it just creates maintenance burden.

How do you keep the cost of running large language models under control as usage grows?

What they are checking: Awareness of token costs, caching, model choice and routing, which decide whether a product is sustainable.

What practices do you put in place so your team ships AI features with tests and observability, not just demos?

What they are checking: Engineering discipline applied to AI work, where it is tempting to skip testing because outputs vary.

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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 We are seeking an experienced Software Engineering Manager to lead a team responsible for designing, building, and operating cloud-native AI agents and tools. In this role, you will provide technical and organizational leadership for a team developing enterprise-scale AI Assistant that transform how Caterpillar customers, dealers, and employees interact with digital products. You will oversee the end-to-end delivery of AI-powered applications and services, including agentic based architecture, agent orchestration framework and tools services, and observability solutions. The ideal candidate combines strong people leadership with hands-on technical expertise in modern software engineering and Generative AI technologies. What You Will Do • Lead and develop a high-performing team of software engineers responsible for AI agent and AI tooling development. • Drive technical strategy, architecture, and execution for cloud-native AI solutions. • Oversee the design, development, deployment, and operation of AI agents, agent orchestration, and supporting services. • Partner with product owners, architects, data scientists, business stakeholders, and engineering teams to define and deliver AI-enabled capabilities. • Establish engineering best practices, coding standards, testing frameworks, security controls, and operational excellence processes. • Own service reliability, scalability, performance, and production support for AI applications and platforms. • Lead release planning, resource allocation, project execution, and risk management across multiple initiatives. • Drive continuous improvement in engineering productivity, software quality, observability, and automation. • Develop team capabilities through coaching, mentoring, career development, and succession planning. • Foster a culture of innovation, experimentation, collaboration, and accountability. • Ensure compliance with enterprise security, governance, and responsible AI requirements. What You Will Have • Organizational Leadership: Proven ability to lead software engineering teams and deliver results through others. Experience building highly engaged teams and developing engineering talent. • Software Development: Deep understanding of modern software engineering principles, design patterns, and development practices. Experience leading the delivery of distributed cloud-native applications. • Software Architecture: Experience designing scalable, resilient, and maintainable software platforms. Ability to evaluate architectural tradeoffs and guide technical decisions. • Software Quality & Operations: Experience establishing testing strategies, observability standards, monitoring practices, and incident management processes. Knowledge of reliability engineering, security best practices, and operational excellence. Considerations For Top Candidates: • Proven experience leading engineering teams. • Experience building AI assistants, digital copilots, autonomous agents, or AI-powered business applications. • Experience with AI evaluation, model observability, prompt management, and experimentation frameworks. • Experience working with cloud AI services and leading foundation models such as OpenAI, Anthropic Claude, Gemini, or open-source alternatives • Understanding of LLMs, RAG architecture, tool-calling patterns, prompt engineering, and agent orchestration frameworks. • Familiarity with frameworks such as LangGraph, LangChain, Semantic Kernel, CrewAI, or similar technologies. • Experience building and operating applications on major cloud platforms such as AWS, Azure, or Google Cloud. • Knowledge of containerization, CI/CD pipelines, infrastructure-as-code, and platform operations. • Strong proficiency in Python, Go, Java, or similar programming languages. • Strong knowledge of Agile development • Experience working in Azure DevOps Summary Pay Range: $147,760.00 - $240,110.00 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: September 30, 2026 - October 11, 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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