Senior Technical Project Manager

Senior Technical Project Manager

Remote, U.S. (Los Angeles preferred)

About the Role

We are looking for a technical project manager with product aspirations to join Sidebench, an LA-based digital product studio that designs and builds custom software, with a focus on healthcare and mission-driven work.

This is not a ticket-running PM seat and it is not an IT delivery role. You will own the hard part of our engagements: running discovery well enough that the build is de-risked before a line of code is written. You will sit between our clients, our design team, and our engineering team (including offshore partners), shape what gets built, and stay accountable for shipping it.

You will run 2 to 4 concurrent engagements at any time and be the named person in the client room, not a voice behind a PMO. If you want variety, autonomy, and real ownership of outcomes, this is built for that. If you want a single-product, governance-heavy, predictable seat, this is not it.

What You Will Do

• Lead product discovery: stakeholder and user research, problem framing, and turning ambiguity into a clear, scoped plan.
• Facilitate client workshops and working sessions, not just status meetings.
• Own scoping and estimation: turn a discovery into a realistic plan, budget, and timeline.
• Drive delivery: budget and timeline ownership, risk management with proposed mitigations, and coordination across design and engineering, including offshore teams across a timezone gap.
• Make and chase technical decisions with healthy diligence. You will not have to write the code, but you will need to know enough to be dangerous and to push back when something does not add up.
• Use AI to make the delivery process better, not just to produce individual deliverables. Improving how we work is part of the job.

What We Are Looking For

• 5+ years running software projects, with a track record of shipping custom software (designed and built for the client), not configuring or implementing a vendor platform.
• A genuine interest in healthcare and/or social-impact work, with at least some exposure to it. Deep healthcare experience is a plus, not a requirement.
• Real product instinct: you have run discovery, shaped solutions, and influenced what got built. You think in user problems, not just scope and dates.
• Technical fluency: you understand the technical tradeoffs well enough to facilitate them and to keep a team honest.
• Client-facing maturity: you can lead a room, manage stakeholders, deliver hard news early, and push back appropriately.
• Comfort running multiple concurrent engagements and coordinating cross-functional and offshore teams.

Dealbreakers (Please Read Before Applying)

• A background that is purely IT (infrastructure, ITSM/helpdesk, ERP or EHR configuration, vendor implementations) with no custom software design and development experience is not a fit for this role.
• This is a hands-on, accountable seat. If your experience is primarily PMO governance or program oversight without ownership of what shipped, this will not be the right match.

Application

Include a short portfolio or 2 to 3 project examples, and a few sentences on why this role interests you. We read these.