Entry Level Technical Project Manager Jobs in Chicago, IL

Location: Remote/Hybrid (Strongly Preferred: Chicago, IL or Southeast Michigan
Reports to: Chief Technology Officer 

About Town Square Health

Town Square Health is reimagining what healthcare can be. We’re building a first-of-its-kind value-based care model with a singular mission: to set the gold standard for how Americans experience healthcare. Our primary care locations offer comprehensive primary care with coordinated specialty support for Medicare-eligible patients, and we’re growing fast, with expansion into multiple markets on the horizon. If you’re bold, collaborative, and driven to make a real difference in people’s lives, we’d love to have you on our team!

The Opportunity

This is not a traditional project management role.

Town Square Health is seeking a Technical Project Manager to own the operational infrastructure of our technology organization — and grow into a genuine thought partner on product strategy as business fluency deepens. This is a hands-on, high-trust role for an organized, process-minded operator who thrives at the intersection of technology execution and business strategy.

You’ll start by running the machinery: sprints, stakeholder meetings, cross-domain dependencies, and status reporting. Over time, as you build fluency in our value-based care model, you’ll take on more roadmap and prioritization ownership. This role is designed to grow — from operational execution to strategic partnership — as the organization scales.

You’ll have the opportunity to:

• Build and own the operational infrastructure that keeps a fast-moving technical org aligned and on track
• Develop deep fluency in value-based care and apply it to real prioritization and roadmap decisions
• Work directly with the CTO and senior leadership as a trusted coordination layer across engineering, operations, and business teams
• Grow the role over time — from operational ownership to strategic partnership — as the organization scales

What You’ll Do

Your responsibilities will evolve as you build context and trust within the organization. Here’s how we think about the progression:

Operational Infrastructure - From Day One

• Run sprint ceremonies including planning, standups, and retrospectives
• Prepare, schedule, and facilitate stakeholder meetings; manage follow-up and ensure nothing falls through the cracks
• Track cross-domain dependencies and surface blockers proactively before they become problems
• Keep project execution and reporting tools accurate and up to date

Cross-Domain Coordination & Growth - By 90 Days

• Own the plan-to-design-to-execute iteration loop with CTO guidance
• Drive cross-domain coordination meetings and own follow-through across teams
• Begin contributing to roadmap and prioritization conversations
• Demonstrate enough business model fluency to make independent prioritization judgments

Strategic Ownership - Long Term

• Drive the prioritization process and manage resourcing across the technical org
• Run planning cycles independently, with minimal guidance
• Serve as the primary coordination layer between engineering, business, and external stakeholders

Who You Are

You’re an operator at heart — someone who finds genuine satisfaction in bringing order to complexity and making sure the right things happen at the right time. You don’t wait to be told what needs tracking; you build the system, maintain it, and flag what others miss.

You’re also a fast learner. You can absorb a new business model, connect it to technical decisions, and start making useful judgments quickly. You’re comfortable starting in an execution-focused role and earning your way into strategic ownership over time.

Most importantly, you believe healthcare can be better — and you want to be part of the team proving it.

Qualifications

• 2-3 years of experience as a Technical Project Manager
• Demonstrated ability to manage multiple workstreams simultaneously without losing track of details or dependencies
• Strong written communication skills — produces clear status updates and documentation without prompting
• High learning velocity — able to absorb a complex business model and apply it to real decisions quickly
• Process builder mindset — energized by creating structure, not just following it
• Familiarity with OKR frameworks and project management tools (Smartsheet or similar)
• Exposure to healthcare or B2B SaaS environments strongly preferred
• Excellent collaboration and communication abilities across technical and non-technical audiences
• Mission-driven, collaborative mindset and a passion for improving access to high-quality primary care

What We Offer

• Starting salary range of 85,000-100,000, commensurate with experience
• Comprehensive benefits package (medical, dental, vision, 401K)
• Flexible hybrid work model, with preference for candidates who can work in-person 1–2 days per week in our Chicago, IL or Ann Arbor, MI locations
• Opportunity to build something from the ground up
• Direct impact on how care is delivered to older adults
• High visibility and influence in a growing organization
• Collaborative, mission-driven team

Equal Opportunity Employer

Town Square Health is proud to be an equal opportunity employer. We believe that diverse perspectives and backgrounds make our team stronger and our mission more powerful. We welcome and encourage applications from all qualified individuals regardless of race, color, religion, sex, national origin, age, disability, veteran status, or any other legally protected characteristic. At Town Square Health, everyone belongs.

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