Technical Project ManagerLocation: Remote/Hybrid (Strongly Preferred: Chicago, IL or Southeast Michigan)Reports to: Chief Technology OfficerAbout Town Square HealthTown 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 OpportunityThis 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 trackDevelop deep fluency in value-based care and apply it to real prioritization and roadmap decisionsWork directly with the CTO and senior leadership as a trusted coordination layer across engineering, operations, and business teamsGrow the role over time — from operational ownership to strategic partnership — as the organization scalesWhat You'll DoYour responsibilities will evolve as you build context and trust within the organization. Here's how we think about the progression:Operational Infrastructure - From Day OneRun sprint ceremonies including planning, standups, and retrospectivesPrepare, schedule, and facilitate stakeholder meetings; manage follow-up and ensure nothing falls through the cracksTrack cross-domain dependencies and surface blockers proactively before they become problemsKeep project execution and reporting tools accurate and up to dateCross-Domain Coordination & Growth - By 90 DaysOwn the plan-to-design-to-execute iteration loop with CTO guidanceDrive cross-domain coordination meetings and own follow-through across teamsBegin contributing to roadmap and prioritization conversationsDemonstrate enough business model fluency to make independent prioritization judgmentsStrategic Ownership - Long TermDrive the prioritization process and manage resourcing across the technical orgRun planning cycles independently, with minimal guidanceServe as the primary coordination layer between engineering, business, and external stakeholdersWho You AreYou'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.Qualifications2-3 years of experience as a Technical Project ManagerDemonstrated ability to manage multiple workstreams simultaneously without losing track of details or dependenciesStrong written communication skills — produces clear status updates and documentation without promptingHigh learning velocity — able to absorb a complex business model and apply it to real decisions quicklyProcess builder mindset — energized by creating structure, not just following itFamiliarity with OKR frameworks and project management tools (Smartsheet or similar)Exposure to healthcare or B2B SaaS environments strongly preferredExcellent collaboration and communication abilities across technical and non-technical audiencesMission-driven, collaborative mindset and a passion for improving access to high-quality primary careWhat We OfferStarting salary range of 85,000-100,000, commensurate with experienceComprehensive 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 locationsOpportunity to build something from the ground upDirect impact on how care is delivered to older adultsHigh visibility and influence in a growing organizationCollaborative, mission-driven teamEqual Opportunity EmployerTown 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.