15five - Senior DevOps Engineer
Requirements
• 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. • 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. • 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. • 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 • 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. • We offer amazing benefits that align with our values and culture at 15Five. • Your Health & Wellbeing • Medical, dental, vision with 15Five cost subsidy • Employer paid Short-Term, Long-Term Disability, and Term LifeFamily planning support with enhanced medical plans and consultation programs
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.
Benefits
• Access to mental health and wellness resources • Flexible Time Off Program • Generous paid leave for new parents • Paid Company Holidays • Sabbatical Program • 401K with 4% Matching after 6 months • Work with experts in leadership, culture, and personal development • For more information see: • Our Mission, Vision, & Values -https://www.15five.com/about • Our People and Culture -https://www.15five.com/about/careers • Our Personal & Professional Development Resources -https://www.15five.com/resources/content-library • Reading over the role description and feeling like you don’t check every box? That’s okay; if you think you have what it takes but don’t necessarily meet all the criteria, please apply—you could be exactly who we are looking for! • 15Five follows equitable hiring practices. Our compensation programs are designed to attract, motivate, and retain talented employees who are highly engaged, high performing, and have an exceptional impact on the business and our customers. • The salary range displayed on each job posting reflects the target for new hire salaries for the role across all US locations. Within the range, individual pay is determined by budget allocated for the role and additional factors, including job-related competencies and skills, experience, and relevant education or training. Please note that the compensation details listed in US job postings do not reflect added total compensation including equity or benefits. • In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.
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