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Updated weekly · Last refresh Oct 17

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 daily.

50questions
~8htotal time
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1
CodingStart here. 25 questions · ~227 min
Binary Addition of StringsEasy
Practice
Recently asked

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

Oscar Insurance
Interweaving Strings CheckMedium
Practice
Recently asked

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

Oscar Insurance
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2
Execution5 questions · ~45 min
Spec and Implement Full-Stack FeatureHard
Recently asked

Explain how you would turn an ambiguous feature request into a scoped, tested, and deployable full-stack implementation.

business requirementsapi designcross-functional executionOscar Insurance
Sizing Claim ProcessorsMedium
Recently asked

Evaluates analytical thinking and capacity planning for Oscar Health claims workflows.

capacity planningOscar Insurance
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3
System Design10 questions · ~91 min
Design Pastebin-Style SystemMedium
Recently asked

Evaluates system design fundamentals, tradeoffs, and scalability considerations for a web application.

system designOscar Insurance
O(1) Queue OperationsHard
Recently asked

Design a queue whose get, enqueue, and dequeue operations each run in constant time.

class structureQueuelow latencyOscar Insurance
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4
Behavioral & Leadership7 questions · ~63 min
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5
More topics3 questions · ~27 min
Join Members and ClaimsMedium
Recently asked

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

JoinsdatabaseOscar Insurance
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
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Hands-on SQL practiceWrite and run real queries in the editor. 3 drills · ~30 min
The finish line: interview-readyComplete all 50 questions plus 3 hands-on drills to finish this plan.