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Senior Associate, Strategic Operations

Hopscotchprimarycare

Chicago (Chicago, Remote) permanent

Posted: December 16, 2025

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Job Description

About Hopscotch Primary Care

At Hopscotch Primary Care, we believe great healthcare should be accessible to all people across all communities. Today, almost 20% of Americans live in a rural community, yet only 11% of physicians practice in those same communities. We are on a mission to transform healthcare in rural America. We provide high-quality primary care tailored to meet the needs of our patients through our robust care model and comprehensive care team, delivering care in our clinics, and across settings, and wrapping resources around the patients who need them most.

Our patients and the care teams who serve them sit at the center of everything we do at Hopscotch. Hopscotch Primary Care takes a team approach to serve patient needs and provide the best care possible. Our goal is to provide the care each of us would want for ourselves or for our family members, in the right setting, and at the right time.

Today, we are serving thousands of patients in our value-based care model and the number is growing every day. If you want to bring your experience, skill and passion to make a lasting impact in healthcare, we’d like to meet you.

ABOUT THE ROLE 

We are looking for a Senior Associate to support our Strategy & Operations team, which plays a pivotal role in driving both the strategic growth and operational excellence of Hopscotch. This individual will be responsible for leading strategic, operational, and analytical initiatives for high-leverage areas of the business and quickly drive results. The ideal candidate has strong analytical skills paired with first principles thinking and an ownership mentality.

WHAT YOU’LL DO

• Work with the leadership team to pinpoint the highest leverage opportunities and needs across the business

• Scope, design, and execute pilot programs to test new operating models and care model innovations

• Identify, evaluate, and execute strategic opportunities (e.g., joint ventures, partnerships, new service lines)

• Identify and validate new opportunities to apply generative AI to improve access and quality of care

• Support build vs. buy vs. partner assessments and assist in high-impact capital allocation decisions

• Build and maintain complex financial and operational models and reporting to support decision-making

• Lead new market analyses to guide geographic expansion

• Monitor regulatory changes and federal/state funding opportunities impacting care delivery, digital health, and value-based models

ABOUT YOU

• You thrive in the dynamic, fast-paced environment of a start-up

• You are a self-starter with an ownership mindset

• You are results-driven and skilled at focusing time and effort on key priorities  

• You are extremely detail-oriented

• You challenge the status quo to figure out the optimal way to execute your work

• You are an exceptional communicator and can make the complex simple   

• You collaborate effectively with executive-level stakeholders

• You have strong business acumen and exceptional critical thinking skills

• You have a low ego and are willing to get scrappy

• You are passionate about transforming rural healthcare

TARGET QUALIFICATIONS:

• 2+ years of work experience in fast-paced environment such as management consulting, investment banking, or early-stage startup

• Experience working in digital health or healthcare delivery

• Familiarity with value-based care and key healthcare industry dynamics/trends

• Experience leading complex, cross-functional projects with minimal guidance

• Experience presenting to and collaborating with executive leadership

• High proficiency with Excel, PowerPoint, and AI tools (e.g., ChatGPT, Claude)

At Hopscotch Primary Care, we embrace diversity, invest in a culture of inclusion and positivity and encourage all to apply to join our team. You will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

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