Manager; AI Evaluation Engineering

Caterpillar Inc.; Chicago (IL); On-site; USD 148,000 - 240,000; Full time

Benefits offered by this job

Medical benefits

Dental and vision

401(k)

HSA

FSAs

Career development

Incentive bonus

Disability benefits

Life Insurance

Parental leave

Tuition Reimbursement

Job summary

Caterpillar Inc. in Chicago, IL, seeks a leadership role within Cat Digital to evaluate and validate cutting-edge GenAI solutions and guide the development of AI-driven experiences for customers and dealers.

You will drive engineering best practices, ensure high-quality AI products, and scale processes across hybrid cloud and edge environments with a focus on LLMs, tool orchestration, and rigorous evaluation methodologies.

Qualifications

• Experience leading software quality, test automation, validation and AI evaluation teams.
• Delivery of enterprise-scale software and GenAI solutions across hybrid cloud and edge environments.
• Strong knowledge of modern software engineering practices and AI tooling.

Responsibilities

• Provide technical direction to ensure alignment with goals and successful evaluation of AI projects.
• Oversee performance of team members and identify training needs.
• Own the quality of AI engineering products and enforce best practices in development.

Skills

GenAI architecture

LLMs

Prompt engineering

AI evaluation

Observability

CI/CD

Tools

Azure

AWS

GCP

SageMaker

Job description

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.

Career Area

Technology, Digital and Data

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.