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Oscar Insurance Operations Manager Interview Questions

The questions to prepare for a Oscar Insurance Operations Manager interview. Questions from real interview reports rank first. Updated weekly.

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1
ExecutionStart here. 7 questions · ~56 min
Plan a Phased Operations RolloutMedium

Plan a phased rollout for a new operational initiative with clear stages, success criteria, and risk controls.

Launch Planningphased rolloutsProject ManagementOscar Insurance
Drive Cross-Functional ExecutionMedium

Explain how you would align operations, engineering, supply chain, and customer-facing teams to execute a shared initiative.

Stakeholder ManagementExecutioncross-functional collaborationOscar Insurance
Improve a Cross-Functional ProcessEasy

Describe how you improved a process or system by aligning stakeholders, defining success, and managing execution risks.

Success CriteriaRoadmappingScope ManagementOscar Insurance
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2
Strategy4 questions · ~32 min
Penny Debate StrategyEasy

Tests structured thinking and ability to defend a position with clear tradeoffs.

Decision Makingcritical thinkingBusiness AcumenOscar Insurance
Utilization Management Case StudyHard

Tests strategic thinking and operational problem solving for utilization management scenarios.

case studyOscar Insurance
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3
Behavioral & Leadership14 questions · ~112 min
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4
More topics3 questions · ~24 min
Define Operations KPI HierarchyMedium

Design an operations KPI hierarchy that links team performance to customer impact and business results.

North Star MetricKPIkpi hierarchyOscar Insurance
Project Management and Process ImprovementMedium

Evaluates your ability to manage projects and improve processes in an operations setting.

sqlProject ManagementOscar Insurance
Operational KPIs and Team PerformanceMedium

Tests KPI selection and data-driven performance management for operations teams at Oscar Insurance.

KPIDiagnosisOscar Insurance

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Hands-on SQL practiceWrite and run real queries in the editor. 3 drills · ~30 min
Weekly Service KPI by TeamMedium
Practice
Practice drill

Analyze weekly service delivery performance by team using joins, a CTE, date aggregation, and KPI calculations.

KPIJoinssqlDeloitteReputation
SQL for Sales and LogsHard
Practice
Practice drill

Aggregate completed Shopify sales and admin logins by merchant and month using CTEs, LEFT JOIN, and conditional logic.

case studysqlShopify
Identify Funnel Bottlenecks in OnboardingHard
Practice
Practice drill

Use joins, CTEs, and aggregations to find the weakest step in an onboarding funnel and estimate lost conversions.

Funnel AnalysissqlDiagnosisAtlassianRevolut
The finish line: interview-readyComplete all 28 questions plus 3 hands-on drills to finish this plan.