Manager; AI Evaluation Engineering

Mundelein Elementary School District 75; Chicago, Northern (IL, KY); Hybrid; USD 148,000 - 240,000; Full time

Benefits offered by this job

Medical, dental, and vision benefits

401(k) savings plans

Health Savings Account (HSA)

Flexible Spending Accounts (FSAs)

Career Development

Incentive bonus

Job summary

Caterpillar Inc. is seeking an AI Engineering leader within the Cat Digital AI Engineering team to drive evaluation and validation of cutting-edge generative AI solutions, intelligent agents, and digital assistants.

You will shape product development and guide engineering practices across hybrid cloud and embedded environments, focusing on scalable, reliable AI systems. Responsibilities include providing clear technical direction, overseeing team performance, and ensuring quality across all AI

Qualifications

• Proven experience leading software quality, test automation, validation, and AI evaluation teams.

Responsibilities

• Provide strong technical direction to align the team with company goals for evaluating advanced AI projects.
• Oversee performance of individuals and the team, identifying training and development needs.
• Own the quality of AI engineering products and ensure robustness and high standards.
• Establish and supervise engineering best practices to maintain development excellence.

Skills

AI leadership

GenAI architecture

CI/CD

AI evaluation

Team coaching

Observability

Education

CS/AI-related advanced degree

Tools

Azure

AWS

SageMaker

LangChain

LangGraph

Langfuse

Arize

Job description

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.

Job Summary:

Join the AI Engineering team of Cat Digital and take charge of leading a team dedicated to evaluating and validating our advanced generative AI solutions-including intelligent agents, digital assistants, and other innovative capabilities. You will shape the development of cutting-edge products that redefine how customers and dealers interact with technology through AI-driven experiences.

What You Will Do:

• Providing strong technical support and clear direction to ensure the team is aligned with company goals and capable of evaluating advanced AI projects.
• Overseeing the performance of both individual team members and the team as a whole, fostering a culture of learning by identifying and addressing training and development needs.
• Taking ownership of the quality of AI engineering products, making sure all solutions are robust, reliable, and meet high standards.

• Establishing and supervising the implementation of engineering best practices to maintain consistency and excellence in development processes.

What You Will Have:

• Products and Services: Knowledge of major products and services and product and service groups; ability to apply knowledge of product and service appropriately to diverse situations.
• 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 Quality Assurance and Testing: Knowledge of software quality assurance and testing; ability to apply appropriate processes, tools, and techniques for assuring a high level of quality in computer software products and systems.

Considerations For Top Candidates:

• Proven experience leading software quality, test automation, validation, and AI evaluation teams, with the ability to scale processes, tools, metrics, and engineering practices across multiple products and enterprise initiatives.
• Demonstrated success delivering enterprise-scale software and GenAI solutions across hybrid cloud and embedded/edge environments, leveraging modern software engineering practices including CI/CD, automated testing, incident management, feature flags, and progressive deployment strategies (e.g., blue/green and canary deployments).
• Deep expertise in GenAI architecture and system design, including LLMs, SLMs, multimodal, speech, and real-time models; prompt engineering; agentic systems; tool use and orchestration; RAG architectures; vector databases, embeddings, and chunking strategies; fine-tuning techniques such as LoRA; and emerging standards including MCP and A2A.
• Hands-on experience with AI development and evaluation ecosystems, including Azure, AWS, GCP, Azure AI Foundry, SageMaker, Bedrock, Snowflake Cortex, LangChain, LangGraph, Langfuse, Arize, LangSmith, Humanloop, Ragas, DeepEval, Phoenix, or similar technologies.
• Deep understanding of AI evaluation methodologies and the challenges of non-deterministic systems, including metric design, RAG quality assessment, output reliability, safety evaluation, A/B testing, human-in-the-loop validation, and balancing deterministic and probabilistic testing approaches.
• Expertise in modern AI observability and monitoring practices, including tracing, telemetry, evaluation data collection, root-cause analysis, and the use of AI technologies to enhance testing through automated test generation, synthetic data creation, scenario expansion, and LLM-assisted evaluation.

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 1, 2026 - September 20, 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.