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Senior Associate, Strategy & Operations

Hopscotch Primary Care, Chicago, IL, United States


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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, 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 a 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.

Seniority level Mid‑Senior level

Employment type Full‑time

Job function Business Development and Sales

Industries Technology, Information and Internet

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