Senior DevOps Engineer II

Bring a Trailer, part of the Hearst Autos family, operates an enthusiast vehicle marketplace and community. The Senior DevOps Engineer II will modernize and maintain the platform infrastructure, lead its migration to AWS, develop engineering and AI-enabled tooling, and ensure systems are secure, scalable, and reliable.

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
• This is a remote role and may be performed from one of the following states: CA, CO, DE, FL, IL, IN, MD, MI, MN, NY, NC, OH, PA, RI, TX, VA, WA, or WI
• 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