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.

The InfraSec & DevOps team covers security, IT and DevOps for 15Five, a leader in performance-management software. We favor automation over manual toil, infrastructure as code, clear documentation, blameless incident reviews and a sustainable on-call rotation.

Strong candidates at the DevOps Engineer II level are also encouraged to apply.

Role & Responsibilities

• 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.

Experience Required

• 5+ years in DevOps, SRE or infrastructure engineering for Senior (3+ years for DevOps Engineer II).

• 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.

• Experience building and maintaining CI/CD pipelines.

• Configuration management with Ansible.

• Strong scripting in Python and/or Bash, and Git-based workflows.

• Monitoring and alerting with Datadog or similar tools, plus hands-on on-call and incident response experience.

• 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.

• Comfort owning projects end to end on a small team.

Additional Nice to Haves:

• 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.

• Familiarity with Django or other Python web applications.

• Experience supporting distributed teams across US and EU time zones.

Tech Stack

• Cloud and containers: AWS (EKS, RDS/PostgreSQL), Kubernetes, Docker

• Infrastructure as code and configuration: Terraform/Terragrunt, Helm/Helmfile, Ansible

• Delivery: CI/CD pipelines, Git

• Observability: Datadog, VictorOps on-call paging

• Network and security: Cloudflare, DNS, MTA-STS

• AI: MCP servers, LLM integrations, Prompt Test Manager

• Collaboration: Jira, Slack, Google Workspace, Guru

Schedule & On-Call Requirements

This is a full-time role that works Monday through Friday during regular business hours (flexible), plus a shared weekly on-call rotation with scheduled after-hours coverage.

Occasional early-morning or evening meetings support US and EU teammates is expected.