Director of Project & Program Management

Gallagher; Rolling Meadows (IL); Hybrid; USD 150,000 - 210,000; Full time

Benefits offered by this job

Competitive compensation

Comprehensive benefits

Career development opportunities

Collaborative culture

Global reach with local impact

Job summary

Gallagher Bassett is seeking a Director of Project & Program Management to lead the AI Solutions and enterprise technology portfolio. You will coach delivery leaders, align with U.S.

claims operations, and partner with ELT to drive strategic initiatives in a hybrid onshore setting. You will oversee multiple squads, transition from waterfall to Agile, and ensure risk, budgets, and governance are managed across the portfolio.

Qualifications

• Bachelor's degree or equivalent experience in business, technology, or related field.

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: 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 decisions needed to the ELT and senior business stakeholders.
• Partner with claims operations, client services, product, architecture, security and vendors so solutions fit how claims are actually handled.
• Maintain oversight of programs that handle sensitive claims data, working with security, privacy, legal and responsible-AI stakeholders to manage risk and compliance.
• Drive continuous improvement in delivery metrics such as predictability, cycle time, quality, and stakeholder satisfaction.

Skills

Project management

Agile transformation

Leadership

Stakeholder management

Communication

Insurance industry knowledge

Education

Bachelor's degree in business, technology, or related field

Tools

Azure DevOps

Planview

Job description

Introduction

At Gallagher Bassett, we're there when it matters most because helping people through challenging moments is more than just our job, it’s our purpose. Every day, we help clients navigate complexity, support recovery, and deliver outcomes that make a real difference in people’s lives. It takes empathy, precision, and a strong sense of partnership—and that’s exactly what you’ll find here. We’re a team of fast-paced fixers, empathetic experts, and outcomes drivers — people who care deeply about doing the right thing and doing it well. Whether you're managing claims, supporting clients, or improving processes, you’ll play a vital role in helping businesses and individuals move forward with confidence. Here, you’ll be supported by a culture that values teamwork, encourages curiosity, and celebrates the impact of your work. Because when you’re here, you’re part of something bigger. You’re part of a team that shows up, stands together, and leads with purpose.

How you'll make an impact

The Director, Project & Program Management will direct the delivery of GB's AI and enterprise technology portfolio as AI Solutions as we continue to grow. Within the AI Solutions on Agile squads, coach and develop our project managers and delivery leaders, and turn complex technical work into clear, decision-ready updates for GB's Executive Leadership Team (ELT). You will bring third-party administrator (TPA) or insurance knowledge so that what we build fits real claims operations. This role is onshore so you can work directly with U.S. claims operations leaders, business stakeholders and the ELT, align in real time with delivery squads and partners, and keep oversight of programs that handle sensitive claims data.

Key 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 (product ownership, delivery leadership, architecture, engineering, data, QA and business analysis).

• Establish and run the delivery operating rhythm: 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 decisions needed to the ELT and senior business stakeholders.

• Partner with claims operations, client services, product, architecture, security and vendors so solutions fit how claims are actually handled.

• Maintain oversight of programs that handle sensitive claims data, working with security, privacy, legal and responsible-AI stakeholders to manage risk and compliance.

• Drive continuous improvement in delivery metrics such as predictability, cycle time, quality, and stakeholder satisfaction.

About You

Required: Requires a University Degree and minimum 7 years prior relevant experience, or equivalent experience.

• Bachelor's degree or equivalent experience in business, technology, or related field.

• 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 third-party administrator (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).

• Ability to work onshore in the U.S. in a hybrid arrangement, in the office as needed.

Preferred Qualifications

• 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 (for example, claims, health, or financial information).

• Agile or program management credentials (for example, PMP, SAFe, CSM or similar).

• Experience working with external vendors and partners across a distributed delivery model.

Compensation and benefits

At Gallagher, we believe supporting our colleagues goes far beyond the role itself. For more information, visit our Benefits page.

• Competitive compensation
• Comprehensive benefits programs designed to support your well-being
• Career development opportunities and ongoing learning
• A collaborative, people-first culture with accessible leadership
• The opportunity to do meaningful work with global reach and local impact

At Gallagher, we are dedicated to building an inclusive and authentic workplace. If your past experience doesn’t align perfectly, we encourage you to join our Talent Community to stay connected to additional career opportunities. At times, we will consider transferable skills from previous roles.

Gallagher is an affirmative action/equal opportunity employer (Minorities/Females/Veterans/Disabled)