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Project Manager, Enterprise Transformation

Alera Group

Chicago, Illinois

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JOB DETAILS
SKILLS
Brokerage, Cadence, Change Management, Communication Skills, Compensation and Benefits, Continuous Improvement, Cross-Functional, Follow Through, Leadership, Organizational Skills, Plan Meetings, Process Improvement, Project Planning, Project Tracking, Project/Program Management, Risk, Risk Analysis, Risk Management, Status Reports, Strategic Planning, Team Lead/Manager, Team Player, Time Management
LOCATION
Chicago, Illinois
POSTED
30+ days ago
OVERVIEW

Project Manager - Enterprise Transformation
Remote | National collaboration required

At Alera Group, we help businesses navigate risk with confidence. As we continue to evolve and scale, our Enterprise Transformation Office plays a critical role in driving strategic initiatives that improve how we operate and deliver for our clients. We're hiring a Project Manager, Enterprise Transformation to support the planning, coordination, and execution of enterprise-wide transformation efforts.

This role is ideal for someone who thrives in a fast-paced, highly collaborative environment and brings strong execution discipline, organization, and communication skills to complex initiatives.
About Alera Group
Founded in 2017, Alera Group has grown to become the 14th largest broker of U.S. business. We are passionate about our clients' success in Employee Benefits, Property & Casualty Insurance, Retirement Plan Services, and Wealth Services. With offices nationwide, our collaborative approach allows us to deliver national strength with local service.
About the Role
The Project Manager, Enterprise Transformation plays a key role in ensuring transformation initiatives are well-planned, effectively tracked, and delivered on time. You'll partner closely with Transformation leadership, workstream leads, technology teams, and functional stakeholders to keep initiatives aligned, organized, and moving forward.

This role enables leaders to focus on strategic decisions while you drive execution - ensuring clarity, accountability, and momentum across workstreams.
What to Expect
  • Opportunity to work on high-impact, enterprise-wide initiatives
  • Close partnership with senior leadership and cross-functional teams
  • A fast-paced environment where organization and execution drive success
  • Competitive compensation and comprehensive benefits package
  • A collaborative culture focused on continuous improvement and transformation
Why Alera Group
Meaningful Impact
Your work directly contributes to how we evolve as an organization, improving processes, systems, and client outcomes at scale.

Growth & Learning
You'll gain exposure to enterprise-level transformation initiatives and expand your experience across business and technology functions.

Collaborative Culture
You'll work alongside engaged leaders and teams who value partnership, transparency, and shared success.

If you're someone who enjoys bringing structure to complexity and driving meaningful progress across teams, we'd love to connect.

RESPONSIBILITIES

What You'll DoDelivery & Workstream Management
  • Own and maintain detailed project and workstream plans, including milestones, dependencies, and deliverables
  • Ensure plans are realistic, current, and aligned with enterprise transformation priorities
  • Track progress, identify risks to timelines or scope, and partner with stakeholders on recovery actions
Schedule, Risk & Dependency Management
  • Maintain visibility into key milestones, priorities, and upcoming decisions
  • Own and manage RAIDD logs, proactively escalating risks, issues, and blockers
  • Track and coordinate dependencies across teams to minimize disruption
Governance, Reporting & Execution Discipline
  • Develop clear, concise status reports and materials for leadership and governance forums
  • Support operating cadence through meeting coordination, agenda preparation, and decision tracking
  • Maintain visibility into actions, ownership, and follow-through
Cross-Team Coordination & Alignment
  • Align plans, reporting, and assumptions with Transformation Management Office standards
  • Coordinate across business, technology, and external partners to support integrated delivery
  • Partner with Change Management and Communications to align execution with adoption and readiness
Continuous Improvement
  • Contribute to the refinement of transformation delivery practices, tools, and standards
  • Identify opportunities to improve execution efficiency and team effectiveness
QUALIFICATIONS

What You BringRequired
  • Bachelor's degree or equivalent professional experience
  • 5+ years of project or program management experience
  • Experience supporting enterprise transformation or large-scale business/technology initiatives
  • Strong pl

About the Company

A

Alera Group

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