Digital Strategy Manager Jobs in Chicago, IL (NOW HIRING)

Technology, Digital and Data

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.

The Digital Adoption and Customer Success (DACS) team within Cat Digital is in search for a Lead Digital Strategy Manager. They will be responsible for strategizing, project managing, and helping to execute strategic priorities and projects across complex, cross-functional initiatives and teams. This position works in close partnership with leadership, the engagement team, and product multi-stakeholders to align organizational priorities, strengthen operational rhythms, and drive structured oversight of multiple complex digital projects to completion.

• Manages day-to-day project delivery activities, coordinating with the team on stakeholder alignment, communications, and change readiness.
• Develops contingency plans for delivery, dependency, and adoption risks; escalates issues with clear options and impacts for business and technical stakeholders.
• Clarifies competing priorities, supports data-driven decision making, and ensures momentum and accountability across complex digital engagement work
• Partners with leadership to translate strategic objectives into actionable roadmaps, ensuring alignment between long-term vision and near-term execution
• Evaluates and manages deliverables to ensure agreed outcomes are achievable, developed, and met; aligns delivery milestones with engagement, training, and rollout readiness plans provided by the team
• Monitors project results for significant deviations; ensures adherence to quality standards and processes; incorporates stakeholder feedback and early adoption signals into delivery adjustments.
• Shapes and maintains a cohesive operating rhythm, including the task to align cross-functional teams around shared outcomes, ensuring dependencies, trade-offs, and resource allocations are clearly understood and optimized
• Champions a culture of strategic- thinking, encouraging teams to connect day- to day execution with broader business impact

• Planning: Tactical, Strategic: Knowledge of effective planning techniques and ability to contribute to operational (short term), tactical (1-2 years) and strategic (3-5 years) planning in support of the overall business plan, including sequencing delivery milestones with stakeholder engagement and adoption activities.
• Project Administration: Knowledge of project administration best practices and ability to use organizational strategies, practices and tools for administering projects, including governance routines and communication cadences.
• Decision Making and Critical Thinking: Knowledge of the decision-making process and associated tools and techniques; ability to accurately analyze situations and reach productive decisions based on informed judgment, facilitating timely decisions across business and technical stakeholders.
• Project Control and Reporting: Knowledge of project control and reporting; ability to monitor the vital signs of a project while managing its progress and delivery schedule, including surfacing risks that may affect stakeholder readiness and adoption.
• Project Management: Knowledge of project management; ability to plan, organize, monitor and control projects using appropriate technical resources, partnering with engagement/change resources to enable successful rollout and value realization.
• Standards, Procedures & Policies: Knowledge of standards and policies; ability to utilize a variety of administrative skill sets and technical knowledge to manage organizational policies, standards, and procedures, ensuring project governance aligns with enterprise expectations and stakeholder commitments.

• Extensive experience in program/project management concepts including project charters, scheduling and milestones, scope management, risk/issue management, governance and reporting
• Proven ability to engage stakeholders and communicate effectively, with a strong emphasis on cross-functional collaboration.
• Strong leadership presence, able to motivate teams, hold them accountable to commitments, and drive clarity and momentum in ambiguous situations.
• Strong cross‑functional collaborator, comfortable navigating multiple partners (internal and external) and resolving issues that span business, product, and engineering.
• Highly organized, detail‑driven, and structured, with a track record of managing backlogs, schedules, risks, and dependencies across multiple teams.
• Demonstrated experience building or refining delivery processes, with the ability to create predictive, efficient, and scalable ways of working that align to PMO standards
• Ability to identify and incubate new opportunities, including process improvements, capability gaps, and innovation initiatives that drive business growth.
• Strong storytelling skills, with the ability to synthesize complex information into clear, compelling narratives tailored for a variety of audience types
• Proven ability to lead through change, including driving adoption of new processes, tools, or organizational shifts.

$128,470.00 - $192,710.00

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.

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.

August 25, 2026 - September 6, 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.