Senior DevOps Engineer II

Bring a Trailer, part of the Hearst Autos family, operates a trusted enthusiast marketplace for classic, collector, and enthusiast vehicles. The Senior DevOps Engineer II will modernize infrastructure, support migration to AWS, build developer tooling including AI-agent workflows, and ensure secure, scalable, highly available systems. The role also supports WordPress platforms, troubleshooting, CI/CD, and rotating 24/7 on-call operations.

Responsibilities:

• Develop and maintain infrastructure via automation
• Maintain current infrastructure while leading the charge as we migrate to AWS
• Develop applications which help software engineers do their jobs at a faster pace with less overhead, including tooling that incorporates AI agents into the development and operations workflow
• Work closely with development teams to architect and implement applications in a secure and highly available manner
• Apply Spec Driven Development practices to translate requirements into clear, testable specifications before implementation, including for AI-assisted and agent-driven workflows
• Continued support and modernization of WordPress Bring A Trailer website and backends
• Troubleshoot and identify root cause of issues in a complex environment
• Provide 24/7 on-call support on a rotating basis

Requirements:

• 8+ years of experience deploying and supporting high-traffic, scalable web applications and services
• 5 years working in the AWS serverless environment, including Cognito, Lambdas, Step Functions, DynamoDB
• Experienced with Terraform, or Typescript and the AWS CDK
• Proficient scripting knowledge (Linux, Unix shell scripts, Python, Ruby, etc.)
• Hands-on experience in Configuration Management and Deployment tools
• Mastery of CI/CD tools on AWS native services and third-party tools
• Building CI/CD pipelines & competency in GIT
• Excellent knowledge of SDLC
• Define AWS Multi-Account strategies based on SLDC practices using Amazon Organizations
• Experience integrating SCM, Code Quality, Code Coverage, and Testing tools for CI/CD pipelines
• Exposure to application and infrastructure monitoring tools
• Experienced with the pricing calculator to forecast accurately AWS billing based on utilization
• Practical experience working with AI coding agents and agentic engineering workflows (e.g., agent-driven code generation, automated review, agent-orchestrated operational tasks) as part of a modern software delivery pipeline
• Familiarity with Spec Driven Development — writing and maintaining specifications that drive implementation, testing, and AI agent behavior
• Extensive experience with and/or certifications for the following AWS Services:
  • AWS Serverless
  • CDK
  • CloudFormation or Terraform
  • CodePipeline
  • GitHub
  • GitHub Actions
  • Lambda / Step Functions
  • SQS
  • SNS
  • Kinesis
  • DynamoDB
  • EventBridge
  • X-Ray
  • CloudWatch
  • WAF
  • DataLake Formation
  • Experience with MySQL
  • Experience with ElasticSearch
• AWS Certified DevOps or AWS Certified Solution Architect
• Experience in a consumer-focused technology company
• Experience with or domain knowledge in the automotive industry, with two-sided markets, or ecommerce generally
• Experience building or operating internal tooling/platforms that integrate AI agents into developer or DevOps workflows