Freelance Remote Operations Engineer Jobs in Chicago, IL

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.
Be Part of What's Next in Autonomous Construction Sites
Construction autonomy is one of the most complex challenges in applied AI, and at Caterpillar, advancements in physical AI, simulation, sensing, and edge computing are turning things that once felt impossible-intelligent machines operating in dynamic jobsites-into reality.
If this work motivates you, we invite you to join our team. In these roles, you'll work at the intersection of the physical and digital worlds. You'll help design and deliver intelligent systems that enable machines to perceive their environment, make informed decisions, and support safer, more productive operations.
Job Summary:
As a Product Manager on CAT Digital's Autonomy team, will help defines the vision and roadmap for software that orchestrates autonomous machine operations. This team will define and deliver the digital platform that plans work, assigns tasks to autonomous machines, and tracks execution in real time. This role will have an emphasis on exception management and remote operation of machines. You will work on a fast-paced team to quickly test and iterate on concepts, partnering closely with customers. Upon conception definition, you will partner with software engineering, design, and machine engineering to bring scalable, production-grade autonomy solutions to market.
This role will help shape a fundamental transformation in the construction industry, moving from operator-driven machines to intelligent, software-defined operations. These tools will redefine how the world builds, enabling safer, more efficient, and more predictable operations at global scale.
What You Will Do:

• Help shape the vision for how autonomous operations impact jobsite process, and the offboard application needs to deliver on that new process. In particular, how remote operation can complement and support autonomous operation.
• Collaborate with Design and User Research teams to develop prototype solutions (including using AI tools), test with customers, and gather feedback
• Prioritize new features, enhancements, feedback and bugs into product backlog
• Define clear, well-structured business features, and coordinate with application engineering and platform engineering to deliver
• Partner with marketing and dealer support teams to support adoption and sales growth
• Coordinate with field support specialists and customers to address and resolve problems and expand product usage.

What You Will Have:

• Product Management Skillset: Capability to define product direction in a new and undefined space; can handle ambiguity and set priorities for a product backlog
• Software Product Business Knowledge: Experience with the business aspects and operation of a software product; ability to manage install base, current uses, future plans, and product vision.
• Rapid Prototyping: Working knowledge on the use of AI tools develop concepts for testing with users and collection of feedback
• Effective Communications: Extensive understanding of effective communication concepts, tools and techniques; ability to effectively convey complex concepts to a range of different stakeholder types.
• Decision Making and Critical Thinking: Extensive knowledge of the decision-making process and associated tools and techniques; ability to accurately analyze situations and reach productive decisions based on informed judgment.
• Business Analysis: Working knowledge in identifying business needs, and bring data-driven mindset to quantify and prioritize; ability to recommend solutions that deliver value to stakeholders.
• Software Engineering: Working Knowledge of software engineering; ability to deliver new or enhanced software products.

Considerations For Top Candidates:

• Domain expertise in robotics teleoperation or remote control, gaming, or simulation
• Proven experience within Product Management (typically 5+ years)
• Typically, a Bachelor's or Master's degree, preferably in computer science, information systems, engineering or related field
• Extensive experience leading a technical team while simultaneously managing multiple projects (typically 3+ years)
• Extensive experience with the Agile methodology
• Demonstrated ability to communicate appropriately to ensure a team's success
• Highly developed interpersonal skills to deal with sensitive, emotional or potentially controversial situations.
• Excellent oral and written communication skills
• Strong accountability, teamwork, and interpersonal skills, and communication skills

Additional Information:
This position will be based out of either our Chicago, IL or Peoria, IL offices.
#LI
#BI (used to post on Built In Chicago)
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:
August 10, 2026 - August 16, 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.
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