Strategy Associate Jobs in Chicago, IL (NOW HIRING)

At Gallagher Benefit Services, you’re a trusted partner to organizations navigating some of their most important people decisions. We help clients build better workplaces, where people feel supported, empowered, and inspired to thrive. Whether it’s shaping benefit strategies, designing wellbeing programs, or advising on workforce challenges, the work you do here creates meaningful change for businesses and the people who power them.

We’re a community of bold explorers, trusted experts, and compassionate partners; working side by side to solve problems, and shape the future of work. Here, curiosity is encouraged, collaboration is second nature, and your ideas have room to grow.

If you’re looking for a place where your contribution matters and where you can help build a better world of work; think of Gallagher.

Welcome to Gallagher - a global community of people who bring bold ideas, deep expertise, and a shared commitment to doing what’s right. We help clients navigate complexity with confidence by empowering businesses, communities, and individuals to thrive. At Gallagher, you’ll find more than a job; you’ll find a culture built on trust, driven by collaboration, and sustained by the belief that we’re better together. Whether you join us in a client-facing role or as part of our brokerage division, our benefits and HR consulting division, or our corporate team, you’ll have the opportunity to grow your career, make an impact, and be part of something bigger. Experience a workplace where you’re encouraged to be yourself, supported to succeed, and inspired to keep learning. That’s what it means to live The Gallagher Way.

Your Way Insurance is a people-first organization built on compassion, integrity, and service. Our greatest strength lies in our talented and driven team, dedicated to helping seniors find Medicare plans that truly fit their needs, the right way. Through our one-stop shopping experience, we make it easy to compare top national health insurance carriers and choose coverage with confidence.

As a Senior Strategy Associate, you will play a key role in solving complex business problems, driving cross-functional initiatives, and helping shape the strategic direction of the organization. This individual will partner closely with executive leadership to identify opportunities, evaluate business performance, launch new initiatives, and implement operational improvements across the organization. The ideal candidate combines strong analytical capabilities, structured problem-solving skills, project leadership experience, and executive communication skills.

• Drive real business results through unilateral ownership of strategic initiatives with accountability directly to Executive leadership; initiatives include launching new products, expanding distribution channels, and improving sales and operational performance.
• Apply structured problem-solving methodologies to frame business challenges, develop hypotheses, analyze data, and implement actionable solutions.
• Lead cross-functional projects across stakeholder groups, including Sales, Operations, Finance, Compliance, and Technology.
• Develop and present executive-level analyses, recommendations, and project updates to senior leadership.
• Own data analysis, insights gathering, and report creation to improve both management and operational decision making.
• Mentor junior team members and demonstrate leadership through accountability, influence, collaboration, and project ownership.

Required: Bachelor's degree in Business, Economics, Engineering, Mathematics, Computer Science, or another STEM-related field; MBA is a plus. & 5 years related experience required.

Preferred:

• 3-6 years of experience in management consulting, corporate strategy, business operations, or a related field; experience with leading consulting firms preferred.
• Strong structured problem-solving skills with the ability to frame complex issues, test hypotheses, and translate insights into execution.
• Advanced analytical and quantitative abilities that translate into business understanding; strong Excel skills and experience with Power BI or similar analytics tools expected.
• Excellent executive communication and presentation skills, including the ability to build compelling PowerPoint presentations for senior leaders.
• Proven project management and stakeholder management experience leading cross-functional initiatives.
• Demonstrated leadership potential through formal or informal people management, coaching, or team leadership.
• Bachelor's degree in Business, Economics, Engineering, Mathematics, Computer Science, or another STEM-related field; MBA is a plus.
• Healthcare, Medicare, insurance, or startup experience is preferred but not required.
• Entrepreneurial, curious, energetic, competitive, and comfortable operating in a fast-paced environment.

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)