Senior DevOps Engineer
Summary
15Five is hiring a Senior DevOps Engineer (DevOps Engineer II also considered) to join a two-person team running all company infrastructure: AWS/EKS and Kubernetes with Terraform/Helm, PostgreSQL, CI/CD, Datadog monitoring with on-call, security ops (Cloudflare, secrets, audits), and deploying/governing AI tooling like MCP servers and LLM integrations.
Role & Responsibilities
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Cloud infrastructure: design, build, secure and troubleshoot AWS and EKS/Kubernetes, including provisioning, scaling, capacity planning, upgrades and cost optimization with Terraform and Helm.
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Architecture: provide design input on infrastructure and systems for security, scalability, reliability and performance.
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Databases: run PostgreSQL upgrades, backups, restore tests and tuning.
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CI/CD and release engineering: build and improve the pipelines that ship code to production.
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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.
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Disaster recovery: maintain and test backups, failover and DR plans.
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Security and compliance: manage access and secret rotation, patch vulnerabilities, configure Cloudflare network/VPN and email and domain security (MTA-STS), and support audits.
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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.
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Configuration management: maintain Ansible for user access and server configuration, and automate repeatable work.
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Cross-functional support: resolve requests from engineering and business teams, including internal systems, vendor integrations and access provisioning.
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Projects and documentation: scope and deliver infrastructure, operations and AI projects, and keep runbooks and Guru current.
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3 months: onboarded, on the on-call rotation, handling cross-team requests and reviewing infrastructure changes.
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6 months: running incidents end to end, leading a DR or restore test, and owning AI platform operations.
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12 months: independently delivering major reliability, security or cost projects and helping guide DevOps direction.
Experience Required
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5+ years in DevOps, SRE or infrastructure engineering for Senior (3+ years for DevOps Engineer II).
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Deep hands-on experience with AWS and Linux, and with running production Kubernetes (EKS preferred).
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Infrastructure as code with Terraform (Terragrunt a plus) and Helm.
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Experience building and maintaining CI/CD pipelines.
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Configuration management with Ansible.
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Strong scripting in Python and/or Bash, and Git-based workflows.
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Monitoring and alerting with Datadog or similar tools, plus hands-on on-call and incident response experience.
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PostgreSQL administration: upgrades, backups, restores and performance tuning.
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Practical security operations: IAM and access management, secrets, patching and network configuration.
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Clear written and verbal communication with technical and non-technical people.
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Comfort owning projects end to end on a small team.
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Experience deploying or securing AI tooling: MCP servers, LLM APIs, agent frameworks or prompt evaluation pipelines.
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Experience with AI governance: access controls, usage and cost tracking, or acceptable-use policies.
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Cloudflare (Zero Trust/VPN, DNS) and email security (SPF, DKIM, DMARC, MTA-STS).
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Experience supporting SOC 2 or ISO 27001 audits.
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Disaster recovery testing and multi-region resilience.
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Familiarity with Django or other Python web applications.
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Experience supporting distributed teams across US and EU time zones.
Tech Stack
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Cloud and containers: AWS (EKS, RDS/PostgreSQL), Kubernetes, Docker
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Infrastructure as code and configuration: Terraform/Terragrunt, Helm/Helmfile, Ansible
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Delivery: CI/CD pipelines, Git
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Observability: Datadog, VictorOps on-call paging
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Network and security: Cloudflare, DNS, MTA-STS
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AI: MCP servers, LLM integrations, Prompt Test Manager
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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.
Skills
As published by lever · 9 questions · 3 written answers
Basics
Resume/CV, Full name, Pronouns, Email, Phone, Current location, Current company, LinkedIn URL
Short answers (2)
- What is your desired salary range for this role?
- This role may require an in-person interview. Please confirm you would be to travel if needed.
Pick from a list (4)
- We require that candidates provide proof of their legal right to work in the United States after hiring; will you be able to provide this documentation after you are hired?
- Will you now, or in the future require 15Five to commence (sponsor) an immigration case in order to employ you (for example, H-1B or other employment-based immigration case)?
- Does your range reflect Base Pay or On-Target Earnings optional
- Which US time zone do you work from?
Written answers (3)
- Give an example of how you used AI‑assisted development to accelerate delivery while maintaining code quality. What guardrails, evaluation steps, or review processes did you put in place?
- What experience do you have with Kubernetes? Share a specific example of how you utilized your Kubernetes experience to deliver meaningful impact in a role.
- Describe how you have used IaC in the past? Include specific details on the project, what worked and what didn't, and what you learned.