Senior DevOps Engineer

15Five is hiring a Senior DevOps Engineer to own and operate its cloud infrastructure, databases, CI/CD, reliability, security operations, and growing AI platform. The role delivers infrastructure and AI projects, leads incident response, and partners with engineering, IT, security, and business teams.

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

Preferred

EKS preferred

Terragrunt a plus

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

Amazon EKS

Terragrunt

AI Tooling Deployment

AI Tooling Security

MCP Servers

LLM APIs

Agent Frameworks

Prompt Evaluation Pipelines

AI Governance

Access Controls

Usage Tracking

Cost Tracking

Acceptable-Use Policies

Cloudflare Zero Trust

VPN

DNS

Email Security

SPF

DKIM

DMARC

MTA-STS

SOC 2 Audit Support

ISO 27001 Audit Support

Disaster Recovery Testing

Multi-Region Resilience

Django

Python Web Applications

Distributed Team Support

Benefits

Medical, dental, and vision with 15Five cost subsidy

Employer-paid Short-Term Disability, Long-Term Disability, and Term Life

Family planning support with enhanced medical plans and consultation programs

Inclusive Benefits Stipend

Access to mental health and wellness resources

Flexible Time Off Program

Generous paid leave for new parents

Military leave

Paid Company Holidays

Sabbatical Program

401K with 4% Matching after 6 months

Remote work

Work with experts in leadership, culture, and personal development

Company

Strategic performance management platform for employee engagement and development

San Francisco, California, USA

https://15five.com/

Founded in 2011

201-500 employees

Qualifications

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

Infrastructure as code with Terraform

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

EKS preferred

Terragrunt a plus

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

Required skills

AWS, Linux, Kubernetes, Terraform, Helm, CI/CD, Ansible, Python, Bash, Git, Datadog, PostgreSQL, Security Operations, Incident Response

Preferred skills

EKS preferred, Terragrunt a plus, Experience supporting SOC 2 or ISO 27001 audits, Disaster recovery testing and multi-region resilience, Familiarity with Django or other Python web applications

Experience

3+ years