Principal Technical Program Manager

OpenLoop; Toronto; Presencial; CAD 140.000 - 190.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Medical benefits

Dental & Vision

Flexible PTO

401(k) plan

Life & Pet insurance

Descripción de la vacante

OpenLoop is seeking a Principal Technical Program Manager in Toronto to lead high‑impact, cross‑functional programs that align with company OKRs. You will partner with Engineering, Product, and business stakeholders to run Agile delivery across teams and translate business vision into executable technical plans.

In this principal IC role, you’ll help define TPM governance, establish cadence for quarterly planning and roadmaps, mentor aspiring TPMs, and report progress to executives with clear,

Formación

• 8+ years in Technical Program Management or an equivalent strategic technical role.
• 3+ years leading programs that span multiple teams or business units.
• Deep knowledge of Agile software development (Scrum/SAFe).
• Strong technical fluency with systems architecture, APIs, integrations.
• Experience translating complex systems into business language.
• Proven experience driving programs tied to OKRs and measurable outcomes.
• Exceptional written and verbal communication with senior stakeholders.
• Experience writing status reports and program updates for varied audiences.
• Experience defining and using delivery metrics to improve performance.
• Experience mentoring program managers and leading organizational change.

Responsabilidades

• Own and drive execution of complex, cross‑functional technical initiatives tied to OKRs.
• Ensure every request from stakeholders aligns with objectives and measurable outcomes.
• Prioritize with Engineering and business leaders, negotiating scope and timelines.
• Produce status reports and updates for leadership, engineering, and partners.
• Own cross‑team planning, dependency management, and delivery cadence.
• Use metrics and retrospectives to improve efficiency, predictability, and cycle time.
• Set program strategy and quarterly/ multi‑quarter roadmaps aligned to OKRs.
• Define the TPM operating model, intake, prioritization, reporting, and health.
• Lead organizational change and adoption of new delivery practices.
• Provide program data to inform headcount, architecture reviews, and portfolio discussions.
• Maintain TPM documentation and onboarding materials.

Conocimientos

Agile SAFe

Cross-functional

Jira

Backlog mgmt

Epics milestones

Executive comms

Metrics reporting

Capacity planning

Program governance

Influence leadership

Herramientas

Jira

Descripción del empleo

About OpenLoop

OpenLoop was co-founded by CEO, Dr. 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.

About OpenLoop

OpenLoop was co-founded by CEO, Dr. 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.

About The Role

OpenLoop’s mission is to bring care anywhere by powering telehealth solutions at scale. 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. You will act as a trusted advisor to executive leadership, presenting in stakeholder and leadership meetings with C-level visibility and meaningful ownership. You will lead through influence, setting the standard for program leadership and growing the next generation of TPMs at OpenLoop. You will connect engineering and product with the rest of the business so that priorities move forward predictably.

What You’ll Do

• Own and drive execution of complex, cross-functional technical initiatives tied directly to company OKRs.
• Ensure every request from business stakeholders aligns with company objectives and measurable outcomes.
• Make prioritization and tradeoff decisions in partnership with Engineering and business leaders, negotiating across scope, timelines, and impact.
• Produce status reports and updates tailored to the audience: executive summaries for leadership, detailed delivery views for engineering, and updates for business partners.
• Own cross-team planning, dependency management, and delivery cadence across multiple engineering teams.
• Use metrics and retrospective findings to find bottlenecks and improve team efficiency, predictability, cycle time, and delivery health, and communication.
• Set program strategy, consistent operating model cadence engineering and product, including quarterly planning, program reviews, and multi‑quarter roadmaps across portfolios of related initiatives, aligned to company OKRs.
• Define the TPM operating model at OpenLoop, including standards for intake, planning, prioritization, reporting, and delivery health.
• Lead organizational change, such as new delivery practices, tooling, or team structures, and bring stakeholders along.
• Lead delivery during high‑stakes moments, such as critical launches, client escalations, or incidents, keeping teams focused and stakeholders informed.
• Run a consistent operating cadence across engineering and product, including quarterly planning, program reviews, and launch readiness checks.
• 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.

Required Qualifications

• 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 (SAFe).
• 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.
• Proven experience driving programs tied to OKRs and measurable business outcomes.
• 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.
• Strong prioritization and decision‑making skills with the ability to operate autonomously.
• Experience aligning and influencing cross‑functional stakeholders.
• Hands‑on experience using Jira and other project management tools to manage cross‑functional delivery at scale.
• Experience structuring backlogs, defining epics and milestones, and creating executive‑ready reporting dashboards.
• Track record of building or scaling a program management function, including defining processes, tooling, and reporting standards that other teams adopt.
• Experience mentoring and developing program managers, and raising the capability of a team.
• Executive presence, with experience advising C‑level leaders and influencing decisions without direct authority.
• Experience leading organizational change and driving adoption of new delivery practices across engineering and business teams.
• 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.
• Sound judgment under ambiguity, with a history of making high‑stakes decisions and owning the outcomes.
• 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.
• Calm under pressure, bringing structure and clarity to programs that are off track or ambiguous.

Preferred Qualifications

• 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 working in fast‑growing or globally distributed teams.
• 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.

Our Benefits

• Medical, Dental, and Vision plans
• Flexible Spending/Health Savings Accounts
• Flexible PTO
• 401(k) + Company Match
• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.