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15Five is an AI-powered performance management platform that combines generative AI, custom analytics, and human-centered design to help managers lead with impact. The platform includes 360° performance reviews, engagement surveys, goal tracking, manager coaching, and ongoing feedback tools.
As a Senior DevOps Engineer, you will own critical infrastructure and operations across a fast-paced, remote startup. You'll design, build, and secure AWS and EKS/Kubernetes environments, including provisioning, scaling, capacity planning, and cost optimization using Terraform and Helm. You'll provide architectural input on infrastructure and systems for security, scalability, reliability, and performance.
Key responsibilities include: running PostgreSQL upgrades, backups, restore tests, and tuning; building and improving CI/CD pipelines for production deployments; owning Datadog observability and alerting; participating in an on-call rotation with scheduled after-hours coverage; responding to incidents and leading post-incident reviews; maintaining and testing backups, failover, and disaster recovery plans; managing access, secret rotation, and vulnerability patching; configuring Cloudflare network/VPN and email security; deploying and securing MCP servers, LLM integrations, and agent frameworks; managing prompts, skills, and evals in the Prompt Test Manager; maintaining Ansible for user access and server configuration; resolving cross-functional requests from engineering and business teams; and scoping and delivering infrastructure, operations, and AI projects while keeping runbooks current.
Success milestones: at 3 months, you'll be onboarded and on the on-call rotation, handling cross-team requests and reviewing infrastructure changes; at 6 months, you'll run incidents end-to-end, lead a DR or restore test, and own AI platform operations; at 12 months, you'll independently deliver major reliability, security, or cost projects and help guide DevOps direction.
The role operates Monday through Friday during flexible business hours, plus a shared weekly on-call rotation with scheduled after-hours coverage. Occasional early-morning or evening meetings support US and EU teammates.
**Requirements:**
- 5+ years in DevOps, SRE, or infrastructure engineering
- Deep hands-on experience with AWS and Linux, and 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
**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
