Strategy Associate Jobs in Naperville, IL (NOW HIRING)

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.
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Our Newest Opportunity:
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.
We are building out a new function that sits at the intersection of lead generation analytics and enterprise analytics, reporting directly to our Strategy Associate. This is a high-visibility seat for someone who wants exposure across nearly every part of the business-Sales, Operations, Compliance, and beyond-while owning real, tangible problems end-to-end. You'll help shape how we evaluate and optimize our top-of-funnel lead sourcing, while also building out the analytical and technical backbone (including AI-enabled tooling) that lets the rest of the organization make faster, better decisions. If you want outsized ownership, cross-functional exposure, and a direct hand in fixing what's broken-not just diagnosing it-this is the seat.
Responsibilities

• Sourcing Strategy: Assist in evaluating and shaping our top-of-funnel lead sourcing channels, providing data-driven insights to help guide strategic direction and overall channel mix.
• AI & Automation Ownership: Take ownership of AI-enabled tools and workflows after initial strategy and implementation, maintaining, iterating, and expanding their use across lead management and analytics functions
• Funnel & Lead Analytics: Build and maintain reporting that connects vendor performance to downstream funnel outcomes, surfacing insights that drive vendor mix and sourcing decisions
• Cross-Functional Analytics Support: Operate in a dotted-line, matrixed capacity across other departments and business units-standardizing analytics processes, identifying automation opportunities, and driving process improvement wherever data and reporting gaps exist
• Problem Identification & Resolution: Proactively identify breakdowns in process, data, or tooling and drive fixes through an analytical and technical lens, in support of the Strategy Associate's broader roadmap and vision
• Business Partnership: Act as a trusted analytical partner to stakeholders across the business, translating ambiguous problems into clear, structured, data-backed solutions

Qualifications
This role suits someone who wants to build real ownership early in their career-someone equally comfortable digging into data and engaging directly with business stakeholders, who's energized by touching many parts of the business rather than staying in one lane. Successful candidates will have:

• Relevant Experience: 2-3 years of professional experience in management consulting, analytics, or a comparable field; healthcare experience is a plus but not required
• Analytical Rigor: Strong, structured analytical skills with the ability to turn ambiguous problems and messy data into clear, actionable recommendations
• Technical Aptitude: Comfort working with data tools and a genuine interest in AI-enabled and automated workflows; prior exposure to reporting/BI tools (Excel required, PowerBI or similar a plus) and appetite to learn new tools quickly
• Process Orientation: A bias toward fixing root causes, not just flagging them-comfortable owning a problem through to an operational or technical solution
• Vendor/Relationship Awareness: Comfort working alongside external partners, with an ability to evaluate performance and contribute to conversations on cost and quality
• Cross-Functional Comfort: Ability to operate across multiple business units and stakeholder groups simultaneously, prioritizing effectively in a matrixed environment
• Executive Presentation Skills: High level of comfort using PowerPoint and Excel to synthesize complex data into clear, professional briefings for senior management
• Workplace Culture: An enthusiastic, ownership-driven approach to working in a fast-paced, ambiguous environment where scope will evolve
• Education: Bachelor's degree in business, STEM, or a related field

Benefits

• Benefits: Full-time benefits package including health insurance and retirement savings plans
• Learning and Growth: Direct mentorship from leadership, exposure across nearly every business unit, and outsized opportunity for scope and title growth as the analytics function is built out
• Expense Reimbursement: Coverage for travel and industry-related expenses

The typical base pay range for this role nationwide is $70,000 to $80,000 per year.
Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company's performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.
To learn more, visit: www.onedigital.com/careers
OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.
OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information (including testing and characteristics) or any other category protected by federal, state or local law (collectively, "protected characteristics"). A copy of the Federal EEO poster is linked here.
Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant:
City and County of San Francisco
City of Los Angeles
County of Los Angeles
Employment decisions shall comply with all other applicable federal, state and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal history inquiry [or 'ban the box'] laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont and Washington.
In short, we believe in hiring the most qualified applicant for the position, regardless of background.
This posting will remain live while OneDigital is actively accepting applications. Once candidates have been selected, the posting will be removed.
OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow.
If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you.
Thank you for your interest in joining the OneDigital team!