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Oscar Insurance Software Engineer Interview Questions

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

50questions
~7htotal time
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1
CodingStart here. 25 questions · ~221 min
Interweaving Strings CheckMedium
Practice

Use dynamic programming to determine whether one string preserves the order of two interleaved Oscar Health messages.

Oscar Insurance
Binary Addition of StringsEasy
Practice

Add two binary strings without integer conversion using right-to-left digit processing and carry propagation.

Oscar Insurance
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2
Execution5 questions · ~44 min
Optimize Workflow with Python or SQLMedium
Recently asked

Tests practical debugging, performance thinking, and translating bottlenecks into implementable optimizations.

process improvementworkflowoptimizationOscar Insurance
Trade-offs in High-Throughput DatabasesHard
Recently asked

Tests database architecture understanding, consistency/availability trade-offs, and scalability planning.

Trade-offsscalabilityResource AllocationOscar Insurance
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3
System Design10 questions · ~88 min
Global Search and Provider RecommendationsHard
Recently asked

Tests end-to-end search/recommendation architecture, ingestion pipelines, and latency optimization strategies.

latencyRetrievalRecommendation SystemsOscar Insurance
Claims System for Volume SpikesHard
Recently asked

Tests distributed systems design with consistency, scalability, and operational reliability under load spikes.

system designscalabilitydata consistencyOscar Insurance
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4
Behavioral & Leadership7 questions · ~62 min
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5
More topics3 questions · ~27 min
API Gateway for Real-Time CareHard
Recently asked

Tests system design for low-latency messaging, API gateway patterns, and integration across multiple stakeholders.

InfrastructureAPIsOscar Insurance
Join Members and ClaimsMedium

Assesses SQL join skills and ability to model relationships between member and claim data.

JoinsdatabaseOscar Insurance
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Hands-on SQL practiceWrite and run real queries in the editor. 3 drills · ~30 min
SQL Average Selling PriceMedium
Practice
Practice drill

Calculate weighted average selling prices by product using a date-range join, aggregation, and NULL handling.

leetcodesqlCostarCostar Group
Top Customers by Region VolumeMedium
Practice
Practice drill

Find the top 3 customers in each region by transaction volume using joins, aggregation, and window ranking.

Window FunctionsJoinsRankingJPMorganChaseSilicon Valley BankNavi
Monthly Sales Trends by CategoryMedium
Practice
Practice drill

Aggregate monthly sales by product category and use LAG to calculate month-over-month changes.

InfrastructureToolsData WranglingTotal Wine & MoreInc.Benjamin Moore
The finish line: interview-readyComplete all 50 questions plus 3 hands-on drills to finish this plan.