Technical Project Manager

Town Square Health•Chicago, IL

6d•$85,000 - $100,000•Hybrid

About The Position

Town Square Health is seeking a Technical Project Manager to own the operational infrastructure of their technology organization. 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. The role starts with managing sprints, stakeholder meetings, cross-domain dependencies, and status reporting, with the opportunity to grow into roadmap and prioritization ownership as business fluency deepens. The position is designed to evolve from operational execution to strategic partnership as the organization scales. The ideal candidate is an operator at heart, a fast learner comfortable with ambiguity, and driven by a mission to improve healthcare.

Requirements

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

Responsibilities

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