Senior Project Manager

Project Manager – Specialty Insurance Integration
Engagement Type:

Contract

2 Year Contract + Extensions

100% Remote (with initial discovery process and monthly cadence in Chicago, IL)

Two Round interview process

• Proven experience as a seasoned Project Manager leading complex, business-focused initiatives.
• Prior experience within the insurance industry, with a strong appreciation for Specialty Insurance strongly preferred.
• Demonstrated success managing M&A, merger, or large-scale business integration projects.
• Experience working within highly matrixed, cross-functional environments.
• Strong stakeholder management and communication skills, with the ability to influence across varying levels of the organization.
• Ability to manage complexity and ambiguity while maintaining structure, momentum, and accountability.
• Experience using enterprise project management tools; familiarity with Planview is a plus.

• Business-focused Project Manager (not a deep technical or IT Project Manager).
• Comfortable operating in fast-paced integration environments with multiple concurrent work streams.
• Confident, mature, and highly collaborative professional who can partner effectively with senior leaders and functional teams.

Insight Global client made a large acquisition August 2025 and is currently executing a multi-year integration of the two organizations. As part of this effort, the Specialty Integration Workstream is seeking two (2) seasoned Project Managers to support critical initiatives within the overall Specialty Integration plan.

The Project Managers will be aligned to the Specialty Integration PMO and will play a key role in driving complex, cross-functional integration efforts within the Specialty Insurance business.

• Serve as the day-to-day Project Manager for a defined integration track, executing against the Specialty Integration Blueprint.
• Work in close partnership with the Integration Lead, Specialty Integration PMO, and functional workstream leads (e.g., Technology & Data, HR, Finance & Accounting, and other business functions).
• Monitor and control functional area integration plans using the existing project management platform (Planview), ensuring plans are developed, maintained, and executed accurately within the system.
• Maintain data integrity and reporting accuracy within Planview to support upstream governance and executive reporting.
• Facilitate strong cross-functional collaboration across matrixed teams to drive engagement, alignment, and adherence to timelines.
• Proactively identify, track, and report project risks and issues, and support the execution of mitigation and risk management plans.
• Support governance and feedback loops by actively participating in Steering Committee (Steer Co) meetings and Specialty Integration PMO forums, communicating insights, risks, and improvement opportunities as appropriate.