Director, Strategic Initiatives

Gallagher•Rolling Meadows, IL

About The Position

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

Requirements

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

Nice To Haves

Degree in Business, Economics, or related field; MBA preferred
8–10+ years of relevant experience
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
Experience in consulting strongly preferred
Proven ability to structure ambiguous problems and deliver results quickly
Willingness to travel up to 15%

Responsibilities

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 and annual planning priorities
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
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
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

Benefits

Medical/dental/vision plans, which start from day one!
Life and accident insurance
401(K) and Roth options
Tax-advantaged accounts (HSA, FSA)
Educational expense reimbursement
Paid parental leave
Digital mental health services (Talkspace)
Flexible work hours (availability varies by office and job function)
Training programs
Gallagher Thrive program – elevating your health through challenges, workshops and digital fitness programs for your overall wellbeing
Charitable matching gift program