Director of Project & Program Management

Gallagher•Rolling Meadows, IL

2d•Hybrid

About The Position

The Director, Project & Program Management will direct delivery of Gallagher Bassett’s AI Solutions and enterprise technology portfolio as the organization grows. The role supports the transition to Agile squads, develops project managers and delivery leaders, and turns complex technical work into decision-ready updates for the Executive Leadership Team (ELT). It requires insurance or third-party administrator (TPA) knowledge to ensure solutions fit real claims operations. The position is onshore in the U.S. and uses a hybrid arrangement, with in-office work as needed, to support direct collaboration with claims operations leaders, business stakeholders, the ELT, delivery squads and partners, while maintaining oversight of programs involving sensitive claims data. The Director owns end-to-end portfolio delivery, including planning, dependencies, risks, budgets, resourcing and release readiness across concurrent programs. The role establishes delivery practices and governance, coaches project managers, communicates between business and technical teams, presents portfolio information to executives, partners across operational and technical functions, and drives continuous improvement in delivery outcomes.

Requirements

University degree and at least 7 years of prior relevant experience, or equivalent experience.
Bachelor’s degree or equivalent experience in business, technology or a related field.
At least 6 years of project and program management experience delivering technology solutions, including leading multiple programs at once.
Demonstrated experience leading a team or organization from traditional (waterfall) delivery to Agile, including scaling multiple squads.
Experience managing, coaching and developing project managers or delivery leaders.
Working knowledge of the insurance industry, ideally TPA or carrier claims operations.
Ability to explain technical topics to business leaders and business needs to technical teams, in writing and in person.
Experience presenting to senior and executive audiences and driving decisions.
Experience with delivery and portfolio tools such as Azure DevOps and Planview, or comparable tools.
Ability to work onshore in the U.S. in a hybrid arrangement, in the office as needed.

Nice To Haves

MBA or master’s degree in organizational management.
Experience delivering AI, machine learning or advanced analytics solutions.
Experience with programs involving sensitive or regulated data, such as claims, health or financial information.
Agile or program management credentials, such as PMP, SAFe, CSM or similar.
Experience working with external vendors and partners across a distributed delivery model.

Responsibilities

Own end-to-end delivery of the AI Solutions and enterprise technology portfolio, including planning, dependencies, risks, budgets, resourcing and release readiness across multiple concurrent programs.
Partner in the transition from legacy delivery to Agile squads and support scaling from four to eight cross-functional squads.
Establish and run the delivery operating rhythm, including intake and prioritization, business cases, capacity and resource planning, sprint and release cadence, and governance checkpoints.
Coach, mentor and develop project managers; set clear standards and hold the delivery team accountable for results.
Translate complex technical work into clear business updates and business needs into clear technical scope so leaders can make timely decisions.
Prepare and present portfolio status, risks, financials and required decisions to the ELT and senior business stakeholders.
Partner with claims operations, client services, product, architecture, security and vendors to ensure solutions fit claims operations.
Maintain oversight of programs handling sensitive claims data, working with security, privacy, legal and responsible-AI stakeholders to manage risk and compliance.
Drive continuous improvement in delivery metrics, including predictability, cycle time, quality and stakeholder satisfaction.