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AI API Breaking Change Detector

Joseph Kim

Full-time · Job · New_York

About the role

Shipping a breaking API change without a deprecation notice is one of the most reliable ways to destroy developer trust. It happens more often than it should — not because engineering teams are careless, but because tracking backward compatibility across hundreds of endpoints, complex nested schemas, and interdependent client SDKs is genuinely hard at scale. We build developer experience tooling for platform engineering teams. Our breaking change detector analyzes API diffs — comparing OpenAPI specs, GraphQL schemas, and gRPC protobuf definitions — and classifies changes as safe, breaking, or requiring migration guidance. It integrates into CI pipelines so teams catch breaking changes before they merge. You will extend the detector to handle semantic breaking changes: changes that are syntactically valid but break real client behavior in ways that schema comparison alone cannot detect. The solution involves LLM-assisted semantic analysis of change context.

Responsibilities

  • Extend breaking change detection to semantic API changes beyond schema diffs
  • Build LLM-assisted analysis of change context to detect behavioral breaking changes
  • Implement migration guidance generation for complex breaking change scenarios
  • Design CI pipeline integration for GitHub, GitLab, and Bitbucket workflows
  • Create breaking change severity scoring and categorization system
  • Build evaluation benchmarks from real API migration postmortems

Requirements

  • 3+ years in platform engineering or developer tooling with API design experience
  • Experience with OpenAPI, GraphQL schema, or gRPC protobuf tooling
  • Familiarity with LLM-based analysis and LangChain or similar frameworks
  • Strong Python and API development skills
  • Understanding of semantic versioning and API lifecycle management

Benefits

  • Fully remote
  • Health and dental
  • $3,000 learning budget
  • Equity participation
  • Flexible hours

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Categories

Automation & AI Workflows AI & Machine Learning Engineers

Skills

python fastapi docker sql langchain

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Job Type

Full-time

Level

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Language

English

Salary Range

$100k – $130k / year

AI Expertise

Automation & AI Workflows AI & Machine Learning Engineers

Skills

python fastapi docker sql langchain openai api

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