Director, Tech Strategy & Operations

<p>Hi, we're Oscar. We're hiring a Director, Tech Strategy Operations to join our Technology team.</p> <p>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.</p> <p> </p> <p><strong>About the role:</strong></p> <p>As a Director, Technology Strategy Operations, you will be responsible for driving the overarching strategic direction and operational excellence for Oscar’s technology organization. This role serves as a primary advisor to technology leadership, influencing high-stakes decision-making and driving innovation through large-scale process improvements and strategic initiatives. The role works independently to oversee multi-year roadmaps and ensures alignment with enterprise-level goals. </p> <p>You will report into the Chief of Staff, Technology.</p> <p><strong>Work Location: </strong></p> <p>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</p> <p><strong>Pay Transparency: </strong></p> <p>The base pay for this role is: $218,592.00 - $286,902.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.</p> <p> </p> <p><strong>Responsibilities:</strong></p> <ul> <li><strong>Strategic Leadership:</strong> Orchestrate cross-functional collaboration at the executive level across Technology, Finance, and Product to architect and implement global technology strategies.</li> <li><strong>Operational Excellence:</strong> Establish and report on high-level Technology Operations KPIs and business-aligned metrics to executive leadership and the Board.</li> <li><strong>Roadmap Governance:</strong> Direct the long-term evolution of technology architecture, overseeing multi-year roadmaps for tool evaluation, selection, and implementation.</li> <li><strong>Leadership Development:</strong> Lead and scale a high-performing organization of managers and individual contributors, focusing on mentorship and professional growth.</li> <li><strong>Crisis Risk Management:</strong> Serve as a point of escalation for complex technical issues and proactively identify and mitigate organizational risks.</li> <li>Compliance with all applicable laws and regulations. </li> <li>Other duties as assigned. </li> </ul> <p><strong>Requirements:</strong></p> <ul> <li>Bachelor’s degree in a STEM field or 4+ years of commensurate work experience.</li> <li>10+ years of professional experience in technology strategy, operations, or a related leadership role.</li> <li>7+ years of experience building, coaching, and developing high-performing technical or operational teams.</li> <li>Demonstrated expertise in using data (e.g., Excel, SQL) to influence complex organizational decisions and drive investments</li> </ul> <p><strong>Bonus points:</strong></p> <ul> <li><strong>Advanced Degree:</strong> Master’s degree (MBA or MS in a technical field) preferred</li> <li><strong>Industry Context:</strong> Deep expertise in the healthcare regulatory landscape (e.g., HIPAA) and experience in high-growth or public company environments</li> <li><strong>Methodologies:</strong> Process Improvement or Lean Six Sigma certification</li> <li><strong>Communication:</strong> Proven history of successfully briefing C-suite executives during high-pressure situations.</li> </ul> <p> </p><div class="content-conclusion"><p><span style="font-weight: 400;">This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud</span><a href="http://hioscar.com/careers/recruitment-fraud-alert"><span ... (truncated, view full listing at source)