Project Manager II

Position: Project Manager II
Location: Chicago, IL
Length: 9+ months
Shift: Hybrid Onsite: 2-3 days Onsite a week
Interview: Video

Job Description:
The Project Manager - AI Digital Workplace Enablement supports the execution of the AI Digital Workplace Task Force, whose mission is to integrate high-impact AI and digital workplace tools into core business processes in close collaboration with business unit leadership. This role provides disciplined project management and delivery coordination to ensure Task Force initiatives move efficiently from intake through implementation. The Project Manager partners with Digital Workplace leadership, Product Owners, business stakeholders, internal technology teams, and external vendors to execute prioritized use cases, manage dependencies, and deliver measurable business value while operating within our governance and risk standards.


Department - AI Strategy & Governance


Essential Duties & Responsibilities
Performs a combination of duties in accordance with departmental guidelines:
• Manage end to end delivery of AI Digital Workplace Task Force initiatives from intake through closeout.
• Develop and maintain project plans, timelines, and delivery milestones across multiple workstreams.
• Facilitate agile ceremonies including backlog refinement, sprint planning, daily stand ups, and retrospectives.
• Manage and prioritize backlogs in partnership with Product Owners and stakeholders.
• Coordinate cross functional dependencies across Technology, Information Security, Infrastructure, HR, and business teams.
• Identify delivery risks and issues; drive mitigation and resolution.
• Coordinate work with external vendors and consulting partners, tracking deliverables and timelines.
• Provide clear status reporting and executive ready updates to leadership.
• Maintain project artifacts and delivery documentation in standard tools (e.g., Jira, Confluence).
• Proactively surface tradeoffs and decision points across initiatives, clearly articulating implications to delivery, capacity, and business outcomes.
• May perform additional duties as assigned.


Skills, Knowledge & Abilities
• Strong project management and delivery coordination skills.
• Experience working in Agile or hybrid delivery models.
• Proficiency with Jira or similar tools for backlog and sprint management.
• bility to manage multiple initiatives and complex dependencies.
• Strong organizational, facilitation, and communication skills.
• Comfortable operating in environments with governance, risk, and compliance considerations.
• bility to influence without authority and work effectively across teams.


Education & Experience
• Bachelor's degree in a related discipline, or equivalent experience.
• 3-5 years of experience in project or delivery management.
• Experience building and managing project plans and delivery artifacts.
• Experience supporting technology, digital workplace, or AI initiatives preferred.
• Experience coordinating vendor or consulting partner delivery preferred.
• gile, Scrum, or PMP certification preferred.
• Insurance experience preferred
• Experience navigating large corporate environments