Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states. Our Technical Program Management team turns business vision into structured, measurable execution, bringing operational rigor, predictability, and scale to how OpenLoop plans and ships. We’re hiring a Principal Technical Program Manager to lead high-impact, cross-functional programs that directly support company OKRs and strategic priorities. This is a principal-level individual contributor role and one of the most senior TPM positions at OpenLoop. You will help set direction for how OpenLoop plans, prioritizes, and delivers its most complex, multi-team programs, translating business vision into structured, executable technical programs. You will partner closely with Engineering, Product, and business stakeholders, run Agile delivery across engineering teams, and make sure every initiative is tied to measurable outcomes. You will help lead the build-out of the TPM function at OpenLoop in standardizing Agile and practices, defining reporting cadences, and providing delivery metrics that improve how teams plan and ship. Own and drive execution of complex, cross-functional technical initiatives tied directly to company OKRs. Own cross-team planning, dependency management, and delivery cadence across multiple engineering teams. Provide program data on capacity and resourcing to inform headcount planning, architecture reviews,



and portfolio discussions. Keep TPM documentation and onboarding materials current so the practice runs as a repeatable discipline, not on any one person's knowledge. 8+ years of experience in Technical Program Management or an equivalent strategic technical role, including 3+ years leading programs that span multiple teams or business units. ~ Deep working knowledge of Agile software development, such as Scrum and the Scaled Agile Framework (Protected). ~ Strong technical fluency (not required to be an engineer) with the ability to understand systems architecture, APIs, integrations, and technical dependencies. ~ Demonstrated experience translating complex systems into business-friendly language. ~ Exceptional written and verbal communication skills, with a track record of presenting to senior stakeholders and executives. ~ Experience writing status reports and program updates tailored to different audiences, from executives to engineering teams. ~ Experience defining and using delivery metrics (velocity, predictability, cycle time, health indicators) to improve team performance. ~ Hands-on experience using Jira and other project management tools to manage cross-functional delivery at scale.



~ Track record of building or scaling a program management function, including defining processes, tooling, and reporting standards that other teams adopt. ~ Ability to connect technical roadmaps to business strategy, budget, and resourcing decisions. ~ Experience leading through influence across senior leaders and peers, including resolving conflict and aligning teams with competing priorities. ~ Track record of coaching others into stronger program leaders, with examples of people you have helped grow or promote. ~ Experience shaping team structure, hiring, or leveling for a program or project management team. ~ Track record of finding and resolving delivery risk before it becomes a customer or launch issue. ~ Experience building capacity and resource plans, and using data such as velocity and burndown to forecast delivery. ~ Certified ScrumMaster (CSM), Professional Scrum Master (PSM), or SAFe certification (e.g., SAFe Scrum Master, SAFe Release Train Engineer, SAFe Agilist). Experience in healthcare, health tech, virtual care, care delivery platforms, or healthcare operations. Experience with clinical, pharmacy, or technical integrations. Experience delivering AI or machine learning projects, such as LLM-powered features, automation, or AI integrations, from scoping through launch. Hands-on use of AI tools and experience introducing AI-assisted workflows to a team and measuring their effect on delivery speed and quality. Medical, Dental, and Vision plans ~ Flexible Spending/Health Savings Accounts ~ Flexible PTO ~Life Insurance, Pet insurance, and more

📌 Technical Program Manager, Data Management, Data Centers (Toronto)
🏢 OpenLoop Health
📍 Toronto