Technical Project Manager

Greater Toronto AreaFull-timemid

OperationsProject Manager

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Quick Summary

Overview

About PocketHealth Burnout, staffing shortages, chronic underfunding — healthcare is under more strain than it has ever been.

Technical Tools

OperationsProject Manager

Burnout, staffing shortages, chronic underfunding — healthcare is under more strain than it has ever been. A disproportionate share of available resources never reach patients; they're consumed by the administrative layer that sits between a provider and the care they deliver.

PocketHealth exists to change that. Our flagship imaging platform gives patients direct, secure access to their medical images and records, trusted by hundreds of hospitals and clinics across North America. Conductor is our agentic AI automation platform — purpose-built to take the administrative weight off healthcare providers so their people and their dollars can go back into care.

About the Role

~2 min read

PocketHealth is looking for a Technical Project Manager to own the execution of complex Conductor deployments with healthcare providers, including hospitals and clinics. This role sits at the intersection of clients, engineering, sales, and customer success, ensuring deployments move quickly, stakeholders stay aligned, and clients successfully launch and expand with Conductor.

You'll manage multiple deployments at once, owning in-depth discovery, scope documentation, timelines, communication, and cross-functional execution from kickoff through go-live. You don't need to be an engineer, but you should understand how systems connect and be able to translate a client's operational reality into scope our engineers can build from. After go-live, you own the outcome metrics and are the first to spot adjacent workflows Conductor could take on next.

This job posting is for an existing vacancy. The salary range for this position is $120,000 - $170,000 annually, depending on the experience and expertise you bring to the team. Salary is just one part of the story, though; this role is eligible for equity in the form of stock options and includes a comprehensive health and benefits package. We view our compensation as a total investment of your well-being, designed to support you in both your work and your life outside of it.

This is a hybrid position with two days a week in our Toronto office, where we collaborate deeply; the rest is yours to work from wherever you do your best thinking.

Every deployment is different. Healthcare providers run similar systems but operate them in ways that diverge in the details, and those details are where automations succeed or fail. Discovery is where we find them. AI is a first-class part of how we work; Claude and AI-assisted workflows are standard practice across the Conductor team, for engineers and non-engineers alike.

Serve as a point of contact for client stakeholders from kickoff through go-live

Build and manage deployment plans, timelines, milestones, dependencies, and risk tracking

Drive deployment cadence through regular status updates and clear ownership across internal and client teams

Plan and coordinate user acceptance testing and drive formal sign-off

Run in-depth discovery sessions on each workflow in scope with the teams who do the work, including scheduling, medical records, and imaging operations

Document current-state workflows and standard operating procedures, including volumes, handoffs, exceptions, and systems involved

Produce scoping documents covering workflow logic, inputs and outputs, edge cases, integration dependencies, acceptance criteria, and success metrics

Define success metrics during discovery so every build is tied to a measurable outcome before development starts

Partner with engineers to resolve open questions, evaluate feasibility and trade-offs, and manage scope changes

Identify blockers, drive resolution, and keep teams aligned toward launch goals

Determine when client requests fall outside contracted scope and require additional scope, resources, or alternative solutions

Maintain deployment documentation and tickets so teams have clarity on priorities and next steps

Track and report outcome metrics for live automations and review them with clients regularly

Identify adjacent workflows Conductor could automate and partner with sales to develop expansion opportunities

Translate patterns across deployments into product feedback and repeatable discovery and delivery templates

5-7 years in technical project management, implementation consulting, solutions delivery, or enterprise implementations, with accountability for execution and outcomes

Experience owning complex B2B deployments involving multiple stakeholders and dependencies, several at a time

Experience working with healthcare providers, or in similarly complex, regulated operational environments

Experience with EHR or RIS/PACS implementations, workflow automation, or integration-heavy enterprise software is a strong plus

Demonstrated ability to produce requirements or scope documentation that engineering teams have built from

Technical understanding of APIs, system integrations, and data flows.

Strong project management skills, including driving timelines, managing risks, and coordinating cross-functional teams

Excellent written and verbal communication with clients, executives, and front-line staff

Process improvement background is a plus

You bring structure to ambiguity and operate independently

You pay attention to the workflows adjacent to the ones you're deploying to expand the impact of conductor

You can manage multiple active deployments without dropping threads or cutting corners

AI is a core part of how you work. You automate your own workflows, prototype and pressure-test ideas with it, and treat it as a multiplier that lets you own more than possible without it.

You hold yourself to a high bar on both documentation quality and client outcomes

You can do amazing things at PocketHealth. You can positively impact the healthcare journey for millions of people, while building your career and developing your skills. It doesn’t have to be one or the other. It has been a part of our mission since our founding to empower patients & make healthcare accessible to all, and we know this can only be achieved with a team of diverse perspectives that is representative of the Patient & Provider communities we serve.

People love working here for these reasons and more: working remotely, our competitive salaries and benefits (including stock options for every employee!), four weeks of paid time off, unlimited paid wellness days, extended mental health coverage, and 16 weeks of parental leave top-up.

We’re proud to foster a culture that embraces diversity, equity, and inclusion, and we believe in caring for our employees with the same thoughtfulness we offer our Patients & Providers.

If there are ways we can support you through the recruitment process with an accommodation, please let us know by reaching out to DEI@pocket.health. Applications are accepted via posting only.