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Weekday AI (YC W21)
Posted 32 days agoVerified live 23h ago

Cloud / DevOps Engineer (Infra & IaC)

Brief overview

Remote
$75–$110/hrStated range
KubernetesTerraformAWS CDKAWS LambdaAmazon API GatewayAmazon DynamoDBCI/CD PipelinesCloud ArchitectureInfrastructure AutomationGitOpsContainerization

About the company

Weekday AI (YC W21) logo
Weekday AI (YC W21)jobs.weekday.works

We are a YC-backed recruitment startup. Find select jobs posted by premium YC as well as VC backed startups here. Hand-curated by Weekday team.

Job description

Summary

Weekday AI is seeking an experienced Cloud / DevOps Engineer to support a cutting-edge GenAI environment. The role focuses on evaluating technical workflows, developing reference solutions, and establishing rigorous standards for AI-generated reasoning across cloud infrastructure, Kubernetes, AWS, Infrastructure-as-Code, and CI/CD.

Responsibilities

  • Collaborate with research and engineering teams to identify knowledge gaps and improve AI model performance across cloud infrastructure, DevOps, Kubernetes, and Infrastructure-as-Code domains
  • Design realistic and technically challenging tasks covering Kubernetes troubleshooting, AWS service integration, infrastructure automation, and production operations
  • Develop accurate, detailed reference solutions for complex infrastructure engineering scenarios
  • Review and evaluate AI-generated technical solutions for correctness, reliability, scalability, security, and adherence to production best practices
  • Provide clear, structured written feedback highlighting technical gaps, incorrect assumptions, and opportunities for improvement
  • Create detailed evaluation criteria, rubrics, and benchmarks for assessing Kubernetes troubleshooting, IaC architecture, AWS integrations, and CI/CD reasoning
  • Develop scenarios involving cluster failures, infrastructure automation, deployment workflows, service integrations, and operational reliability
  • Work closely with other technical subject matter experts to maintain consistency, accuracy, and quality across evaluation datasets
  • Translate practical production experience into structured guidance that can be used to improve AI-generated infrastructure solutions

Skills

  • **4+ years of professional experience** in Cloud Infrastructure, DevOps, Site Reliability Engineering, Platform Engineering, or a closely related field
  • Strong hands-on experience managing **Kubernetes in production environments**, including diagnosing, troubleshooting, and resolving cluster failures and operational issues
  • Experience with Kubernetes beyond simply writing manifests or consuming managed Kubernetes control planes
  • Proven production experience with **Infrastructure-as-Code**, particularly **Terraform and/or AWS CDK**
  • Strong practical knowledge of **AWS cloud services**, including production integration with services such as:
  • AWS Lambda
  • API Gateway
  • DynamoDB
  • Experience designing, implementing, and maintaining **CI/CD pipelines** for production workloads
  • Strong understanding of cloud architecture, infrastructure automation, deployment strategies, observability, reliability, and operational best practices
  • Demonstrated career progression with increasing ownership and responsibility in infrastructure, DevOps, or platform engineering
  • Ability to commit reliably to **40 hours per week during standard weekdays**
  • Excellent written and verbal communication skills, with the ability to explain complex technical concepts and engineering decisions clearly
  • Strong analytical and troubleshooting abilities, particularly when diagnosing distributed systems and infrastructure failures
  • Experience working with large-scale cloud infrastructure or highly distributed systems
  • Familiarity with Kubernetes networking, security, storage, scaling, and cluster lifecycle management
  • Experience implementing infrastructure security and reliability best practices
  • Knowledge of AWS architecture patterns and cloud-native application design
  • Experience with GitOps, containerization, monitoring, logging, and observability platforms
  • Familiarity with modern DevOps and platform engineering methodologies
  • Experience reviewing or evaluating technical documentation, engineering solutions, or AI-generated outputs

Qualifications

Must Haves

  • **4+ years of professional experience** in Cloud Infrastructure, DevOps, Site Reliability Engineering, Platform Engineering, or a closely related field
  • Strong hands-on experience managing **Kubernetes in production environments**, including diagnosing, troubleshooting, and resolving cluster failures and operational issues
  • Experience with Kubernetes beyond simply writing manifests or consuming managed Kubernetes control planes
  • Proven production experience with **Infrastructure-as-Code**, particularly **Terraform and/or AWS CDK**
  • Strong practical knowledge of **AWS cloud services**, including production integration with services such as:
  • AWS Lambda
  • API Gateway
  • DynamoDB
  • Experience designing, implementing, and maintaining **CI/CD pipelines** for production workloads
  • Strong understanding of cloud architecture, infrastructure automation, deployment strategies, observability, reliability, and operational best practices
  • Demonstrated career progression with increasing ownership and responsibility in infrastructure, DevOps, or platform engineering
  • Ability to commit reliably to **40 hours per week during standard weekdays**
  • Excellent written and verbal communication skills, with the ability to explain complex technical concepts and engineering decisions clearly
  • Strong analytical and troubleshooting abilities, particularly when diagnosing distributed systems and infrastructure failures

Nice to Haves

  • Experience working with large-scale cloud infrastructure or highly distributed systems
  • Familiarity with Kubernetes networking, security, storage, scaling, and cluster lifecycle management
  • Experience implementing infrastructure security and reliability best practices
  • Knowledge of AWS architecture patterns and cloud-native application design
  • Experience with GitOps, containerization, monitoring, logging, and observability platforms
  • Familiarity with modern DevOps and platform engineering methodologies
  • Experience reviewing or evaluating technical documentation, engineering solutions, or AI-generated outputs

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