Strategy Associate - Chicago, IL

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that’s making a bigger impact on the world?  At OneDigital, we are on a mission to help people do their best work and live their best lives.  From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other’s truest selves.

We understand that pursuing a new job is a big deal.  Maybe you’re afraid you won’t fit in.  Well, here’s the good news.  For us, the days of “fit in to get in” are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot. Your best life awaits.

Must be eligible to work in the United States without the need for work visa or residency sponsorship.

Our Newest Opportunity: 

Overview

OneDigital Advanced Health is at the forefront of transforming how individuals navigate the complexities of the healthcare marketplace. We have established ourselves as a premier Medicare distributor, dedicated to providing informed guidance, advocacy, and unparalleled access to Medicare Advantage, supplemental, and prescription drug plans. Our mission is simple but powerful: to help seniors and individuals secure health coverage that truly fits their needs, with transparency and confidence.

As part of the broader OneDigital ecosystem—the nation’s largest pure-play employee benefits broker—we combine the agility of a fast-growing, innovative health-tech player with the scale and stability of a global industry leader. We believe that work should be as rewarding as it is impactful. From our modern hub in the heart of Chicago’s Loop to our collaborative, "people-first" culture, we empower our team to innovate, solve complex problems, and drive tangible results.

Our Strategy team serves as the primary engine driving our decision-making and operational execution. We are looking for an ambitious professional to join this core function, where you will directly influence our strategic roadmap, execute high-stakes initiatives, and architect the reporting & AI infrastructure that powers our operations. This is a role for an impact-driven professional who thrives on autonomy and wants to translate vision into results. If you are looking for a place to accelerate your career, take true ownership, and make a genuine difference in the lives of the members we serve, you’ve found it. Join us as we set a higher standard for excellence in the healthcare space.

Responsibilities

• Strategic Execution: Take charge of high-impact strategic initiatives from start to finish, such as rolling out new products, expanding sales channels, and optimizing overall sales results

• Business Partnership: Serve as a primary point of contact for internal stakeholders, driving process efficiencies and providing strategic guidance to Sales, Operations, Compliance, and partner teams

• Executive Communication: Develop executive presentation materials to support analyses, present project progress, and enable communication

• Data & Analytics: Create robust reporting and dashboards to track performance metrics, evaluate business hypotheses, and turn complex data into actionable insights for leadership

• Collaboration: Drive effective teamwork across departments by managing project timelines, aligning stakeholder expectations, and ensuring clear lines of communication

Qualifications

Strategy Associates will leverage skills in structured thinking, data-driven decision-making, and stakeholder/project management to be successful. Successful candidates will have:

• Relevant Experience: 2–5 years of professional experience in management consulting or a comparable field, with a preference for candidates who have worked on healthcare-related projects

• Project Management: Proven ability to handle multiple cross-functional projects at once, consistently meeting deadlines and delivering on key objectives

• Stakeholder Communication: Experience leading project teams and peers, managing day-to-day execution, and facilitating meetings that drive toward clear outcomes and decisions

• Strategic Thinking: A data-driven analytical mindset used to challenge assumptions, guide executive decision-making, and support the successful implementation of new initiatives

• Data Experience: Strong proficiency in Excel for data manipulation and analysis, with bonus points for experience using advanced vis