Director, Strategic Initiatives

Arthur J. Gallagher · Rolling Meadows

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.

Overview

We are seeking a Director, Strategic Initiatives to support the VP, Strategic Planning & Initiatives in driving GB North America’s highest‑priority efforts. This leader will partner closely with senior operational and functional executives to scope, design, and execute initiatives that strengthen our operating model, elevate customer and claimant experiences, enhance efficiency, and accelerate value creation.

This role strengthens GB’s Strategic Initiatives team by leading work that solves real operational problems and accelerates business outcomes.

Example Areas of Focus

Projects may span the full GB North America footprint, including:

Improving claimant and customer engagement and experience
Advancing operational excellence across the claim lifecycle
Finding process improvements across teams that improve efficiency and reduce operating costs
Supporting targeted cross‑sell and growth initiatives
Establishing operating controls to reduce waste and revenue leakage
Clarifying roles, responsibilities, and service expectations across functions

How you'll make an impact

In partnership with the VP, Strategic Planning & Initiatives, you will:

Strategic Alignment & Leadership

Establish trust and credibility with operational leaders and other key stakeholders
Ensure clarity and alignment on initiative's purpose, goals, and expected outcomes
Support the development of GB North America’s strategic roadmap, annual planning, and budgeting

Initiative Planning & Execution

Translate strategic priorities into actionable plans with clear timelines, milestones, and deliverables
Manage initiative scope, resources, interdependencies, and stakeholder expectations
Track progress, surface issues, and drive corrective actions in collaboration with operational leaders
Maintain flexibility and adjust plans based on emerging feedback and business needs

Risk, Change & Value Delivery

Proactively identify risks to success and develop mitigation strategies
Anticipate potential resistance points and partner with leaders to address them
Ensure initiatives deliver measurable value aligned with both the initiative’s objectives and GB’s broader enterprise goals
Support Finance and executive leaders in shaping budget and forecast assumptions tied to key initiatives

Team Development

Model structured problem‑solving, data‑driven decision‑making, and crisp communication
Mentor junior team members and contribute to building a high‑caliber “leadership lab” pipeline for the business

About You

Required

Requires a University Degree or equivalent experience
Minimum 8 years prior relevant experience.

Preferred

Degree in Business, Economics, or related field; MBA preferred
Demonstrated experience leading complex initiatives with cross-functional stakeholders
Strong analytical, problem solving, and communication skills
Ability to influence without authority in a matrixed environment
P&C insurance and/or claims experience strongly preferred
Experience in consulting strongly preferred
Proven ability to structure ambiguous problems and deliver results quickly
Willingness to travel up to 15%

Behaviors

Results‑oriented with a strong sense of ownership and urgency
Pragmatic problem solver focused on value and speed to impact
Data‑driven decision‑maker who knows when to move from analysis to action
Confident communicator able to influence, collaborate, and build trusted partnerships
Operates with integrity, sound judgment, and commitment to GB’s mission and clients

#LI-TJ1

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)