Senior DevOps Engineer

15Five

1d • $115,000 - $140,000 • Remote

About The Position

15Five is hiring a Senior DevOps Engineer to join its two-person DevOps team, which runs the company’s infrastructure. This high-ownership role is responsible for cloud infrastructure, databases, CI/CD, reliability, security operations, and the growing AI platform. The engineer will scope and deliver projects, lead incidents, contribute to architecture decisions, and help shape how 15Five deploys and governs AI tools. The role works closely with engineering squads, IT, security, and business teams.

The InfraSec & DevOps team handles security, IT, and DevOps. Its approach emphasizes automation, 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.

The position is full-time, Monday through Friday during flexible regular business hours, with a shared weekly on-call rotation that includes scheduled after-hours coverage. Occasional early-morning or evening meetings are expected to support teammates in US and EU time zones. The role is remote. The US annual base pay range is $115,000–$140,000. Total rewards include participation in an annual discretionary company bonus program, equity awards, and benefits and wellbeing offerings.

Requirements

• At least 5 years of experience in DevOps, SRE, or infrastructure engineering for the Senior level; at least 3 years for DevOps Engineer II.
• Deep hands-on experience with AWS and Linux, and experience running production Kubernetes; EKS is preferred.
• Experience with infrastructure as code using Terraform; Terragrunt is a plus.
• Experience with Helm.
• Experience building and maintaining CI/CD pipelines.
• Configuration management experience with Ansible.
• Strong scripting skills in Python and/or Bash, and experience with Git-based workflows.
• Experience with monitoring and alerting using Datadog or similar tools.
• Hands-on on-call and incident response experience.
• PostgreSQL administration experience, including upgrades, backups, restores, and performance tuning.
• Practical security operations experience, including IAM and access management, secrets, patching, and network configuration.
• Clear written and verbal communication with technical and non-technical people.
• Ability to own projects end to end on a small team.

Nice To Haves

• Experience deploying or securing AI tooling, such as MCP servers, LLM APIs, agent frameworks, or prompt evaluation pipelines.
• Experience with AI governance, including access controls, usage and cost tracking, or acceptable-use policies.
• Experience with Cloudflare Zero Trust/VPN and DNS, and email security such as SPF, DKIM, DMARC, or MTA-STS.
• Experience supporting SOC 2 or ISO 27001 audits.
• Disaster recovery testing and multi-region resilience experience.
• Familiarity with Django or other Python web applications.
• Experience supporting distributed teams across US and EU time zones.
• Terragrunt experience.

Responsibilities

• Design, build, secure, and troubleshoot AWS and EKS/Kubernetes infrastructure, including provisioning, scaling, capacity planning, upgrades, and cost optimization using Terraform and Helm.
• Provide infrastructure and systems design input focused on security, scalability, reliability, and performance.
• Administer PostgreSQL upgrades, backups, restore tests, and performance tuning.
• Build and improve CI/CD and release engineering pipelines that ship code to production.
• Own Datadog observability and alerting, participate in the on-call rotation, respond to incidents, and lead post-incident reviews.
• Maintain and test backups, failover, and disaster recovery plans.
• Manage access and secret rotation, patch vulnerabilities, configure Cloudflare network/VPN and email and domain security (MTA-STS), and support audits.
• Deploy and secure MCP servers, LLM integrations, and agent frameworks; build AI workflow automations; manage prompts, skills, and evaluations in the Prompt Test Manager; enforce least-privilege access; track AI usage and spend; help shape AI policy; and administer company AI tools.
• Maintain Ansible for user access and server configuration, and automate repeatable work.
• Resolve requests from engineering and business teams, including requests involving internal systems, vendor integrations, and access provisioning.
• Scope and deliver infrastructure, operations, and AI projects, and keep runbooks and Guru documentation current.
• Support US and EU teammates through occasional early-morning or evening meetings.

Benefits

• Medical, dental, and vision insurance with a 15Five cost subsidy.
• Employer-paid short-term disability, long-term disability, and term life insurance.
• 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.
• 401(k) with 4% matching after 6 months.
• Remote work.
• Annual discretionary company bonus program.
• Equity awards.
• Comprehensive benefit and wellbeing offerings.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed