REMOTE Project Manager - Core Dealership Management System (DMS)

Job Description

We are seeking an experienced, hands-on IT Project Manager for a contract role (through December 2026, with strong likelihood of extension) focused on critical monthly migrations within our core Dealership Management System (IDS).

This is a high-visibility, execution-heavy position responsible for leading the remaining legacy store conversions (29 stores left) - a complex, time-sensitive process that occurs only at month-end and involves coordinating 30+ integrated systems and up to 50 stakeholders. The ideal candidate can hit the ground running within 1-2 weeks, thrives on detailed coordination, excels with advanced Excel, and communicates effectively with executives, vendors, and technical teams.

Contract Details

Contract through December 2026 (high probability of extension based on performance)

Remote (US-based)

Occasional travel to Lincolnshire, IL (roughly quarterly or as needed)

Flexibility for overnight/extended hours during cutovers (compensatory time off provided)

Key Responsibilities

Lead monthly End-of-Month (EOM) legacy store conversion projects: full lifecycle from planning and executive alignment through execution, hypercare (the week following go-live), and backlog creation.

Coordinate complex production deployments within strict 8-9 hour overnight windows (typically 11 PM - 2 AM), managing timing and dependencies across 30 upstream/downstream systems and 50+ people.

Build and maintain detailed project plans, resource schedules, and dependency tracking using advanced MS Excel as a core tool (no dedicated PM tooling for certain aspects of this work).

Manage project intake, write user stories, groom backlogs, and improve ticket/process management in Jira (Agile/Kanban).

Serve as the primary communication hub for executive stakeholders, internal teams, and external vendors.

Own vendor coordination and deliverable alignment for both the core monthly conversions and additional minor modernization projects.

Support legacy store migration planning (weeks of executive conversations leading up to each cutover) and drive continuous process improvements in the DMS space.

Illustrative Project

Lead the remaining ~29 legacy store conversions into the standardized IDS platform format. These are intensive, high-stakes initiatives that can only be executed at month-end and require precise orchestration of dozens of systems and stakeholders.

pay rate: 60-70/hour

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Skills and Requirements

12-15+ years of IT Project Management experience, with proven success on complex system migrations or large-scale ERP implementations.

Advanced proficiency in Microsoft Excel for complex tracking, dependency management, and resource planning.

Strong experience writing user stories and managing projects in Jira.

Demonstrated vendor management skills and executive-level communication presence.

Ability and willingness to support overnight/weekend deployment windows during critical periods.

Fast learner who can ramp up quickly and run the full process with minimal hand-holding after 1-2 weeks. Direct experience in automotive, dealership, or retail automotive industry (highly desired).

Background with Dealership Management Systems (DMS) or large-scale ERPs.

Familiarity with SharePoint, Confluence, or similar collaboration tools.

Exposure to AI/LLM tools to drive project management efficiencies (a plus).