Senior DevOps Engineer

15Five, US, Remote

The role

We’re a high-performance, high-purpose team that gives you the chance to Build the Future of Work. We run on High Standards and High Support — holding a high bar for results, ownership, clarity, and disciplined execution, while investing in manager enablement, skill development, and whole-person care. We are committed to a No B.S. environment, meaning we anchor ourselves in truth, course-correct in real time, and expect people to lean into direct conversations.

We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact.

If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply.

15Five is hiring a Senior DevOps Engineer to join the two-person DevOps team that runs all of 15Five's infrastructure. This is a high-ownership role - you will own cloud infrastructure, databases, CI/CD, reliability, security operations and our growing AI platform.

You will scope and deliver projects, lead incidents, contribute to architecture decisions and help shape how 15Five deploys and governs AI tools across the company. You will work closely with engineering squads, IT, security and business teams.

All jobs

Senior DevOps Engineer

15Five, US, Remote

The role

We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact.

If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply.

What you will do

Role & 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.

Your Work Life

Remote work

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.

Senior DevOps Engineer

The role

Senior DevOps Engineer

The role

What you will do

Role & Responsibilities

What Success Looks Like

Your Work Life

For more information see

What you need

Additional Nice to Haves

Tech Stack

Your Health & Wellbeing

Inclusive Benefits Stipend

Flexible Time Off Program

Paid Company Holidays

About 15Five

Similar jobs at other companies