Senior DevOps Engineer

• 15Five is hiring a Senior DevOps Engineer to join the two-person DevOps team that runs all of 15Five’s infrastructure. This is a high-ownership role - you will own cloud infrastructure, databases, CI/CD, reliability, security operations and our growing AI platform
• You will scope and deliver projects, lead incidents, contribute to architecture decisions and help shape how 15Five deploys and governs AI tools across the company. You will work closely with engineering squads, IT, security and business teams
• Cloud infrastructure: design, build, secure and troubleshoot AWS and EKS/Kubernetes, including provisioning, scaling, capacity planning, upgrades and cost optimization with Terraform and Helm
• Architecture: provide design input on infrastructure and systems for security, scalability, reliability and performance
• Databases: run PostgreSQL upgrades, backups, restore tests and tuning
• CI/CD and release engineering: build and improve the pipelines that ship code to production
• Reliability and incidents: own Datadog observability and alerting, take part in the on-call rotation (including scheduled after-hours coverage), respond to incidents and lead post-incident reviews
• Disaster recovery: maintain and test backups, failover and DR plans
• Security and compliance: manage access and secret rotation, patch vulnerabilities, configure Cloudflare network/VPN and email and domain security (MTA-STS), and support audits
• AI platform and governance: deploy and secure MCP servers, LLM integrations and agent frameworks; build AI workflow automations; manage prompts, skills and evals in our Prompt Test Manager; enforce least-privilege access; track AI usage and spend; help shape AI policy; and administer AI tools across the company
• Configuration management: maintain Ansible for user access and server configuration, and automate repeatable work
• Cross-functional support: resolve requests from engineering and business teams, including internal systems, vendor integrations and access provisioning
• Projects and documentation: scope and deliver infrastructure, operations and AI projects, and keep runbooks and Guru current
• What Success Looks Like
• 3 months: onboarded, on the on-call rotation, handling cross-team requests and reviewing infrastructure changes
• 6 months: running incidents end to end, leading a DR or restore test, and owning AI platform operations
• 12 months: independently delivering major reliability, security or cost projects and helping guide DevOps direction

Benefits

• Medical, dental, and vision care
• Fertility consulting assistance
• 24/7 online therapy assistance

• Experience building and maintaining CI/CD pipelines
• PostgreSQL administration: upgrades, backups, restores and performance tuning
• Practical security operations: IAM and access management, secrets, patching and network configuration
• Clear written and verbal communication with technical and non-technical people
• Deep hands-on experience with AWS and Linux, and with running production Kubernetes (EKS preferred)
• Infrastructure as code with Terraform (Terragrunt a plus) and Helm
• Strong scripting in Python and/or Bash, and Git-based workflows
• 5+ years in DevOps, SRE or infrastructure engineering for Senior (3+ years for DevOps Engineer II)
• Comfort owning projects end to end on a small team
• Additional Nice to Haves:
• Monitoring and alerting with Datadog or similar tools, plus hands-on on-call and incident response experience
• Configuration management with Ansible
• Experience deploying or securing AI tooling: MCP servers, LLM APIs, agent frameworks or prompt evaluation pipelines
• Experience with AI governance: access controls, usage and cost tracking, or acceptable-use policies
• Cloudflare (Zero Trust/VPN, DNS) and email security (SPF, DKIM, DMARC, MTA-STS)
• Experience supporting SOC 2 or ISO 27001 audits
• Disaster recovery testing and multi-region resilience
• Experience supporting distributed teams across US and EU time zones
• Familiarity with Django or other Python web applications