Technical Program Manager

Hi, we're Oscar. We're hiring Technical Program Managers to join our Technical Program Management team. 

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Help turn ambitious plans into better healthcare experiences through technology.

Oscar is hiring three Technical Program Managers to join our growing Technology Program Management Office (Tech PMO). By applying to this job post, you will be considered for all Technical Program Manager openings. Specific role placement will be determined following the interview process.

As a Technical Program Manager, you will lead work that helps members navigate their coverage, providers work more easily with Oscar, clinical teams deliver better care, and grow our business. We’re looking for someone who brings curiosity, initiative, and sound judgment. You enjoy understanding how systems work, asking thoughtful questions, and finding a path forward when the answer isn’t obvious. You build trust across teams, make difficult tradeoffs clear, and follow through on the details that turn a good plan into a successful launch.

You’ll partner with Product, Engineering, and business leaders across our Network, Growth, Member, and Clinical pillars. Each hire will support a defined set of teams, combining visibility across their roadmaps with direct leadership of selected complex programs. Your work could span provider data platforms, clinical integrations, member digital experiences, enrollment, broker tools, or marketing technology.

As an early member of a growing Tech PMO, you’ll also help shape how we plan, solve problems, and deliver together. This is an individual contributor role reporting to the Director of the Tech PMO.

You will report into the Director, Technical Program Management.

Work Location:

This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $117,576.00 - $154,318.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Lead complex technical programs from scoping through launch and operational handoff. Build integrated plans with clear owners, milestones, dependencies, and measures of success.
• Turn ambiguity into action. Bring the right people together, clarify the problem, and establish practical next steps.
• Partner with Product, Engineering, and business leaders to connect roadmaps, coordinate commitments, and make scope, sequencing, and capacity tradeoffs explicit.
• Anticipate delivery risks and resolve dependency gaps. Drive timely decisions and escalate with clear options, recommendations, and business impact.
• Coordinate teams and vendors through integrations, testing, adoption, and launch readiness, including required security, privacy, and compliance reviews.
• Support quarterly and annual planning. Give leaders a clear view of progress, what needs attention, and whether delivered work is producing the intended results.
• Help build a strong TPM team: share useful practices, challenge unnecessary process, support colleagues, and turn lessons from delivery into improvements.

Requirements:

• Experience independently leading complex technical programs across multiple teams, from planning through launch and operational handoff.
• Technical fluency to engage engineers on software systems, APIs, data flows, integrations, and implementation tradeoffs.
• Demonstrated ability to bring structure to ambiguous problems and manage dependencies, risks, and competing priorities.
• A record of building trust and influencing decisions across technical and business teams without direct authority.
• Clear written and verbal communication, including the ability to explain complex issues and recommend a course of action to senior leaders.
• Strong ownership and follow-through, with examples of moving work forward when plans change or obstacles arise.

Bonus points:

• Experience in healthcare, health insurance, or another regulated industry.
• Experience in one or more relevant areas: provider platforms, clinical systems, consumer digital products, enrollment, broker or distribution platforms, or marketing technology.
• Experience with external vendors, platform migrations, or complex system integrations.
• Experience improving planning and delivery practices or helping teams adopt new tools and ways of working.
• Experience delivering AI-enabled products or workflow automation, including evaluation and operational readiness.