Senior Project Manager (Software Implementation)

project44 • Chicago, IL

2d • $86,000 - $128,000 • Onsite

About The Position

The Senior Project Manager owns and drives customer software implementation projects from post-sale handover through Go-Live and Hypercare. The role develops and manages project plans, timelines, milestones, budgets, scope, risks, issues, and dependencies, while maintaining alignment among customer and internal teams. The project manager is the primary customer contact for delivery and coordinates cross-functional contributors, including Solutions Architects, Engineering, Product, and Support.

The role leads project governance and stakeholder communications; facilitates kick-off calls, weekly status meetings, steering committees when applicable, and Go-Live readiness reviews; and coordinates System Testing and UAT. It also directs Go-Live planning, cutover, post-launch validation, and Hypercare, then supports transition to Customer Success. The position contributes to process improvements and scalable delivery standards and supports pre-sales and discovery with implementation timelines, delivery approaches, and feasibility input.

This is an on-site role at the company headquarters four days per week, with occasional travel based on customer needs. The role operates in a fast-paced, cross-functional, global environment and expects team members to use AI thoughtfully in their day-to-day work. The posted base salary range is $86,000–$128,000. Total compensation may also include stock options, role-dependent bonus or commission eligibility, and country-specific benefits.

Requirements

• Fluent in written and spoken English.
• At least 5 years of experience in customer-facing project management roles.
• Proven experience managing complex, multi-stakeholder projects with competing priorities and timelines.
• Strong expertise in risk, budget, and stakeholder management.
• Experience with project and collaboration tools such as Jira, Confluence, Microsoft Office, or equivalent.
• Ability to communicate effectively with technical and non-technical stakeholders.
• Strong organizational skills and ability to manage multiple projects simultaneously.
• Comfort working in a fast-paced, cross-functional, global environment.
• Willingness to travel occasionally based on customer needs.
• Ability to work on-site at the headquarters four days per week.
• Ability to use AI thoughtfully, evaluate its outputs critically, and govern it responsibly.

Nice To Haves

• Experience in supply chain, transportation, or logistics technology.
• Experience with SaaS implementations or software delivery.
• Additional language skills, especially French, German, or Spanish.
• Experience with TMS, ERP, or supply chain systems.

Responsibilities

• Own customer implementation projects from post-sale handover through Go-Live and Hypercare.
• Develop and manage project plans, timelines, milestones, and deliverables, aligning internal and customer teams.
• Lead project governance, status tracking, reporting, and stakeholder communication.
• Manage project risks, issues, and dependencies; identify mitigation strategies and drive resolution.
• Manage project budgets and scope to keep delivery within agreed commercial parameters.
• Serve as the primary customer contact for project delivery, communication, and expectation management.
• Coordinate cross-functional teams, including Solutions Architects, Engineering, Product, and Support.
• Facilitate project kick-off calls, weekly status meetings, steering committees when applicable, and Go-Live readiness reviews.
• Coordinate timelines, stakeholders, and deliverables for System Testing and UAT.
• Plan and execute Go-Live, including cutover coordination and post-launch validation.
• Oversee Hypercare and ensure a smooth transition to Customer Success and long-term account stability.
• Track project progress using internal tools such as Jira, Zendesk, Rocketlane, or equivalent.
• Contribute to process improvements, project management standards, and scalable delivery frameworks.
• Support pre-sales and discovery by advising on timelines, delivery approach, and implementation feasibility.
• Travel occasionally based on customer needs.
• Use AI with intent, curiosity, and judgment in day-to-day work.

Benefits

• Stock options for all EOR and project44-employed team members.
• Bonus or commission eligibility depending on role.
• Country-specific benefits that may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed