Technical Project Manager
About the role
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.
What You’ll Do
- 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
- 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
- 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
- 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
- A fast learner — able to absorb a complex business model and apply it to real decisions quickly
- A 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
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
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