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Decagon·Software Engineer·Onsite - System Design / Architecture·Senior

SeniorPrefer not to say
May 2026Remote

Summary

System design round at Decagon focused entirely on building an AI gateway for internal teams routing requests to LLM providers. The scope kept expanding as the interview went on, which was either a feature or a bug depending on how you look at it.

Questions Asked (4)

Q1

Design an AI gateway that internal product teams use to send requests to LLM providers, with a primary provider and a fallback. What does the overall architecture look like?

System DesignAPI & IntegrationsTechnical Trade-offs
Author's notes

This is where I spent most of my time and honestly probably over-indexed on the API gateway and load balancer pieces before getting to the more interesting stuff.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: expected request volume, latency SLAs, cost constraints, and whether streaming is needed. Then present a layered architecture: a stateless gateway service that handles auth, rate limiting, request routing, and provider abstraction, with a primary provider and a fallback provider configured via a circuit breaker. Walk through the request lifecycle, failure handling, and observability, and discuss trade-offs like synchronous vs asynchronous fallback and caching.

Pro tip: Emphasize idempotency and graceful degradation: use idempotency keys to safely retry on fallback, and consider returning a cached or canned response if both providers fail, rather than a hard error. This shows you think about user experience and system resilience beyond just failover.

1. Clarify Requirements and Constraints

Ask about expected QPS, latency SLAs, cost sensitivity, streaming support, and whether responses need to be cached. This ensures your design addresses the right priorities.

2. Define the Gateway's Core Responsibilities

Outline the gateway's role: authentication/authorization, rate limiting, request validation, provider abstraction, routing, and observability. Keep it stateless for horizontal scaling.

3. Design the Provider Routing and Fallback Mechanism

Describe how requests go to the primary provider, with a circuit breaker that trips on errors or latency thresholds and routes to the fallback. Discuss retry policies, timeouts, and idempotency.

4. Detail the Request Lifecycle and Failure Handling

Walk through a request: from client to gateway, auth, rate limit, primary call, fallback on failure, and response. Cover edge cases like partial failures, streaming fallback, and caching.

5. Discuss Observability, Scaling, and Trade-offs

Explain monitoring (metrics, logs, traces), alerting, and how to scale the gateway. Discuss trade-offs: synchronous vs asynchronous fallback, cost vs reliability, and complexity of multi-provider support.

Key Points to Mention

  • Circuit breaker pattern to detect primary provider failures and automatically switch to fallback.
  • Idempotency keys to ensure safe retries and avoid duplicate requests when falling back.
  • Rate limiting and quota management per team to prevent abuse and manage costs.
  • Provider abstraction layer to normalize different LLM APIs and enable easy addition of new providers.
  • Observability: metrics (latency, error rates, fallback frequency), logging, and distributed tracing.
  • Caching strategies for common or deterministic requests to reduce cost and latency.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

What fields would you include in a request log entity for this gateway, and why?

Data ModelingSystem Design
Author's notes

Felt more comfortable here.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the purpose of the request log (observability, debugging, auditing, rate limiting) and the gateway's context. Then propose a minimal but extensible set of fields grouped by category (request metadata, response metadata, timing, error, and context), explaining the rationale for each. Emphasize trade-offs like storage cost, privacy, and query performance.

Pro tip: Mention that you'd avoid logging sensitive data like auth tokens or PII, and suggest using a correlation ID to tie logs across services. Also note that fields should be chosen based on what you need to answer common operational questions (e.g., 'which endpoint is slow?').

1. Clarify the logging goals

Ask or state the primary use cases: debugging, monitoring, auditing, or analytics. This determines which fields are essential versus nice-to-have.

2. Identify core request/response metadata

Include fields like timestamp, request ID, method, path, status code, and client IP. These are fundamental for tracing and basic analysis.

3. Add timing and performance fields

Capture latency (total, upstream, gateway processing) to enable performance monitoring and bottleneck identification.

4. Include error and context fields

Log error codes/messages, user ID (if available), and correlation IDs to support debugging and cross-service tracing.

5. Discuss trade-offs and extensibility

Address storage costs, privacy (avoid PII), and how to extend the schema (e.g., via JSON metadata) without breaking existing queries.

Key Points to Mention

  • Unique request ID and correlation ID for distributed tracing
  • HTTP method, path, query parameters (sanitized), and status code
  • Timestamps (start/end) and latency breakdown (gateway vs upstream)
  • Client IP, user agent, and authenticated user ID (if applicable)
  • Error details (error code, message) and response size
  • Privacy considerations: avoid logging sensitive headers, tokens, or PII

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

How would you ensure full auditability of requests through the gateway, including immutable storage, retention policies, and access control?

System DesignTechnical Trade-offs
Author's notes

Went with append-only log storage, something like S3 with object lock or a write-once audit table.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the audit requirements (what to log, who needs access, compliance needs) and then propose a layered architecture: capture immutable logs at the gateway, store them in a write-once-read-many (WORM) system, enforce retention policies, and implement fine-grained access control. Emphasize trade-offs between performance, cost, and security, and mention how you'd handle sensitive data and scale.

Pro tip: Mention that audit logs should be stored separately from application data with strict access controls, and that you'd use cryptographic hashing or digital signatures to ensure tamper-evidence. Also, consider using a dedicated audit service or sidecar to avoid impacting gateway performance.

1. Clarify requirements and scope

Ask questions to understand what needs to be audited (e.g., all requests, only sensitive operations), who needs access (compliance, security, developers), and any regulatory requirements (GDPR, HIPAA, SOC2).

2. Design immutable logging at the gateway

Ensure every request/response is logged with sufficient detail (timestamp, user, action, resource, status) and that logs are written to an append-only, tamper-evident store (e.g., WORM storage, blockchain-like hash chain).

3. Define retention and lifecycle policies

Specify how long logs are kept based on compliance and business needs, and automate archival and deletion. Consider tiered storage (hot/warm/cold) to balance cost and accessibility.

4. Implement access control and monitoring

Enforce least-privilege access to audit logs using RBAC/ABAC, and log all access to the audit logs themselves. Set up alerts for suspicious access patterns.

5. Address scalability and performance

Discuss how to handle high throughput without impacting gateway latency, e.g., asynchronous logging, buffering, and partitioning. Mention trade-offs between synchronous vs asynchronous logging.

Key Points to Mention

  • Immutable storage: WORM (Write Once Read Many) storage, append-only logs, cryptographic hashing for tamper-evidence.
  • Retention policies: automated lifecycle management, compliance-driven retention periods, secure deletion.
  • Access control: RBAC/ABAC, least privilege, separation of duties, audit log access logging.
  • Data privacy: masking or encrypting sensitive fields in logs, compliance with GDPR/CCPA.
  • Scalability: asynchronous logging, message queues (e.g., Kafka), partitioning, and avoiding gateway bottlenecks.
  • Monitoring and alerting: real-time monitoring for anomalies, integration with SIEM.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q4

The requirements now include caching, PII redaction, and LLM response evaluation. How do you layer these in without redesigning everything?

System DesignAdaptability & AmbiguityTechnical Trade-offs
Author's notes

This came at the end and felt like a stress test.

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AI HintsAI Generated

Suggested Approach

Start by acknowledging that the new requirements are cross-cutting concerns and should be layered as middleware or decorators around the existing LLM pipeline, not baked into core logic. Then walk through each concern—caching, PII redaction, and evaluation—explaining where it fits in the request/response flow and how to introduce it with minimal disruption. Emphasize incremental rollout, feature flags, and observability to validate each layer independently.

Pro tip: Frame the solution as a pipeline of composable interceptors, and mention that you'd start with PII redaction because it's a compliance risk, then caching for cost/latency, and evaluation last since it's non-blocking. This shows you prioritize by business impact, not just technical elegance.

1. Clarify requirements and constraints

Ask about latency budgets, data sensitivity, evaluation frequency, and whether caching should be exact-match or semantic. Confirm that the existing system can be extended without breaking current contracts.

2. Design as composable middleware layers

Propose a pipeline where each concern is an independent interceptor: PII redaction on input, caching around the LLM call, and evaluation asynchronously after the response. This keeps core logic untouched and allows enabling/disabling layers via config.

3. Address ordering and interaction

Explain the correct order: redact PII before caching to avoid storing sensitive data, and evaluate after caching to avoid re-evaluating cached responses. Discuss how layers might interact, e.g., cache keys must account for redaction.

4. Plan incremental rollout and observability

Use feature flags to roll out each layer gradually, with metrics for cache hit rate, redaction accuracy, and evaluation scores. Start with a canary deployment and monitor for regressions.

5. Discuss trade-offs and alternatives

Acknowledge trade-offs: caching may reduce freshness, redaction may impact response quality, and evaluation adds cost. Mention alternatives like sidecar proxies or service mesh for cross-cutting concerns.

Key Points to Mention

  • Middleware/decorator pattern for cross-cutting concerns
  • Order of operations: PII redaction before caching, evaluation after
  • Feature flags and incremental rollout
  • Observability: metrics for cache hit rate, redaction precision/recall, evaluation scores
  • Trade-offs: latency vs. cost, privacy vs. utility, evaluation overhead
  • Avoid redesign by using existing extension points (e.g., interceptors, hooks)

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.