Senior DevOps Engineer

15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use,
delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into change-makers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins.

A career at 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role and every hire meaningfully impacts our trajectory.

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.

The InfraSec & DevOps team covers security, IT and DevOps for 15Five, a leader in performance-management software. We favor automation over manual toil, 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.

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.

Experience Required

• 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.

• 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.

 
 
Additional Nice to Haves:

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.

Tech Stack

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

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. 

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

Inclusive Benefits Stipend

Access to mental health and wellness resources

Your Life

Flexible Time Off Program

Generous paid leave for new parents

Military leave

Paid Company Holidays

Sabbatical Program

Your Future

401K with 4% Matching after 6 months

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.