Director, Strategic Initiatives

Gallagher • Rolling Meadows, IL

2d

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. 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. Demonstrated experience building data-driven business cases using advanced Excel skills (financial modeling, forecasting). In partnership with the VP, Strategic Planning & Initiatives, you will: 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, 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.

Requirements

• Requires a University Degree or equivalent experience
• Minimum 8 years prior relevant experience.
• Demonstrated experience building data-driven business cases using advanced Excel skills (financial modeling, forecasting)
• 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
• Proven ability to structure ambiguous problems and deliver results quickly
• 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
• Experience in consulting strongly preferred
• 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, annual planning, and budgeting
• 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

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: Associate degree