Lead D365 Deployment Specialist

Caterpillar•Chicago, IL

About The Position

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.

Requirements

Customer Focus and Effective Communications Builds strong relationships with dealers and System Integrators, ensuring successful deployment outcomes aligned to business goals.
Anticipates dealer and SI needs, proactively addressing risks and challenges before they impact delivery.
Adapts messaging to suit audience needs, from deep technical discussions to executive briefings.
System Thinking Understands end-to-end deployment ecosystems, including dependencies across applications, integrations, data, and business processes.
Identifies root causes of issues by analyzing interconnected systems and deployment activities.
Business Intelligence & Data Management Applies strong understanding of data structures, data migration processes, and data validation approaches.
Oversees data migration readiness, ensuring quality, completeness, and integrity across deployment phases.
Evaluates and improves data-related processes to support better decision-making and deployment outcomes.
Systems Software Infrastructure Understands system integrations, environments, and infrastructure considerations supporting D365 deployments.
Identifies and escalates integration and environment-related risks impacting deployment timelines or quality.
Technical Troubleshooting Leads resolution of complex deployment issues across D365, integrations, and data migration.
Works across multi-vendor environments to coordinate issue resolution with SIs and Caterpillar teams.
Coaches others on advanced troubleshooting techniques and proactive issue prevention.

Nice To Haves

Proven experience leading deployments of Microsoft Dynamics 365 Finance & Operations (F&O).
Strong working knowledge of Dynamics 365 Customer Engagement (CE) modules.
Demonstrated experience working with and governing System Integrators in large-scale ERP implementations.
Hands-on experience with data migration (strategy, tools, validation, cutover) in enterprise ERP deployments.
Experience in managing complex, multi-stakeholder delivery environments (customer, SI, and product teams).
Understands D365 architecture (F&O and CE), including data models, integrations, and extension patterns.
Reviews and challenges SI design decisions to ensure alignment with Caterpillar standards and best practices.
Strong understanding of ERP deployment lifecycles, methodologies, and governance frameworks.
Experience working with Power Platform ALM, Azure Integration Services and data migration/cutover strategy.

Responsibilities

Lead governance and oversight of System Integrator (SI) execution to ensure adherence to Caterpillar Cat Converge deployment methodology, standards, and playbooks.
Act as the primary Caterpillar deployment lead for assigned dealers, providing guidance and direction throughout the end-to-end deployment lifecycle.
Partner with dealers and SIs to identify risks, issues, and gaps early, and drive resolution through the appropriate Caterpillar product, engineering, and deployment teams.
Provide deep technical and functional expertise in Microsoft Dynamics 365 (F&O and CE) to support solution alignment, troubleshoot issues, and guide decision-making.
Oversee and support data migration strategy, execution, and validation, ensuring data integrity and readiness for go-live.
Conduct and facilitate “risk assessments, root cause analysis, and corrective action planning” across deployment activities.
Review SI deliverables (designs, configurations, data migration plans, integrations) to ensure alignment with Caterpillar architectural and business standards.
Drive accountability with SIs by ensuring delivery commitments, timelines, and quality measures are met.
Communicate deployment status, risks, and escalations clearly to stakeholders, including dealer leadership and Caterpillar leadership teams.
Capture and communicate field feedback to product and engineering teams to continuously improve Cat Converge solutions and deployment processes.
Support continuous improvement of deployment methodologies, tools, and governance frameworks based on lessons learned from active deployments.
Mentor and guide other deployment specialists, fostering best practices and capability development across the team.