Hi, we're Oscar. We're hiring a Technical Program Manager, Data to join our Technical PMO 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:

Lead the data transformation at the core of realizing better healthcare for millions of people.

Oscar is hiring a Technical Program Manager to join our Tech PMO, dedicated to a major enterprise data transformation. You’ll partner closely with Data leadership to lead migration from planning through delivery, protecting the quality and integrity of the data our teams rely on every day.

We’re looking for someone who has experience partnering with Data teams and leading a major enterprise data migration and who brings curiosity, initiative, and sound judgment. You can engage deeply with business partners, data scientists, data engineers, make complex dependencies and tradeoffs clear, and help leaders make timely decisions. You take ownership of execution while building trust with the people who produce and use the data.
Your program will include revamping our data transformation and semantic layers, as well as evolving our data governance and data quality capabilities across the entire business. You’ll coordinate Analytics Engineering, Data Engineering, Data Scientists, Analysts, and business owners through migration, validation, adoption, and operational handoff.

You’ll have the opportunity to shape how Oscar delivers enterprise data programs and help build a strong TPM team. This is an individual contributor role reporting to the Director of the Tech PMO, partnering closely with Data leadership. You’ll lead technical program execution, with Data Engineering accountable for architecture and implementation.

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 - $154,319 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities:

• Own the integrated enterprise data migration plan from scoping through delivery and operational handoff, with clear owners, migration waves, milestones, dependencies, and acceptance criteria.
• Turn ambiguity into action across dbt migration, Cube implementation, data governance, and data quality workstreams. Bring the right owners together and resolve gaps in scope, sequencing, and readiness.
• Partner with Analytics Engineering, Data Engineering, Data Scientists, Analysts, and business owners to map upstream and downstream dependencies, coordinate commitments, and make scope, sequencing, and capacity tradeoffs explicit.
• Anticipate migration risks and drive timely decisions. Escalate with clear options, recommendations, and impact on data quality, integrity, reporting, and business continuity.
• Coordinate data reconciliation, testing, cutover and rollback plans, adoption, and operational readiness. Ensure technical and business owners agree on validation evidence, go/no-go criteria, and required security, privacy, and compliance reviews.
• Support program planning and give Data and executive leaders a clear view of migration progress, readiness, unresolved decisions, and outcomes. Drive business acceptance and clear operational ownership for migrated domains.
• Help build a strong TPM team: share useful practices, challenge unnecessary processes, support colleagues, and turn lessons from delivery into improvements.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned. 

Requirements:

• 5+ years of technical program or project management/process-oriented operations work experience. 
• 2+ years of experience using coding languages such as SQL to analyze project performance and risks and develop erports for management and business owners. 
• Experience independently leading complex software development programs across multiple teams, from planning through launch and operational handoff.
• Technical fluency in data pipelines, transformation layers, data models, semantic layers, lineage, and integrations, with the judgment to challenge migration plans, validation approaches, and implementation tradeoffs.
• Demonstrated ability to structure ambiguous enterprise programs, manage cross-domain dependencies and competing priorities, and coordinate data validation, cutover readiness, and business continuity.
• A record of building trust and influencing decisions across Analytics Engineering, Data Engineering, Data Scientists, Analysts, and business owners, and executive stakeholders without direct authority.
• Clear written and verbal communication, including the ability to translate technical migration risks into business impact 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 with dbt and Cube, or comparable transformation and semantic-layer technologies.
• Experience implementing data governance, data quality controls, lineage, or consistent business metric definitions across domains.
• Experience coordinating external vendors and helping business and analytics teams adopt new data platforms and ways of working.
• Experience migrating business-critical analytics or reporting with staged validation, reconciliation, cutover, and rollback practices.