Manager; AI Evaluation Engineering

Caterpillar Brazil; Chicago, Northern (IL, KY); Hybrid; USD 148,000 - 240,000; Full time

Job summary

Caterpillar Inc. is seeking an AI Engineering lead to guide the Cat Digital AI Engineering team. You will evaluate and validate advanced generative AI solutions, including intelligent agents and digital assistants, shaping AI-driven experiences for customers and dealers.

Leading with a focus on software quality, scalable processes, and modern deployment strategies, you will influence engineering standards and drive innovation across hybrid cloud and embedded environments.

Qualifications

• Proven experience leading software quality, test automation, validation, and AI evaluation teams.
• Experience delivering enterprise-scale GenAI solutions across hybrid cloud and embedded/edge environments.
• Deep expertise in AI evaluation methodologies, observability, tracing, telemetry, and data collection.
• Hands-on experience with modern AI toolchains and AI development ecosystems.

Responsibilities

• 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.

Skills

GenAI architecture

LLMs & multimodal

AI evaluation

CI/CD

Canary deployments

Prompt engineering

RAG architectures

Observability

Tools

Azure

AWS

GCP

LangChain

LangSmith

Bedrock

SageMaker

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

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

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. Visa Sponsorship is not available for this position.

Company Culture

We hire smart, friendly people and it shows in our culture. We hold ourselves to high standards and make sure our values of integrity, excellence, teamwork, commitment and sustainability come to life in the way we work. We make sure our employees feel continuously challenged while also supported. We provide professional growth opportunities, including leadership programs. We celebrate the diversity of our team, while also working together as one Caterpillar. Our culture, like everything at our company, is made possible by each employee’s contribution. Person by person, we create the environment we work in, and we are proud of the Caterpillar we’ve built.