Senior DevOps Engineer

15Five

. Join the two-person DevOps team running all of 15Five's infrastructure .

Posted 10/16/2026full-timeRemote • United StatesSenior💰 $115,000 - $140,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing cloud infrastructure, particularly AWS and Kubernetes, while ensuring security and reliability. Proficient in CI/CD pipeline development, PostgreSQL administration, and implementing AI governance and tooling.

Highest-signal resume keywords

AWS Infrastructure ManagementKubernetes AdministrationCI/CD Pipeline DevelopmentPostgreSQL AdministrationAI Tooling Deployment

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

TerraformAnsiblePython ScriptingBash ScriptingDatadog MonitoringIncident ResponseSecurity OperationsDisaster Recovery TestingAI GovernanceLinux Administration

Soft Skills

Clear CommunicationProject OwnershipCollaboration

Tools & Technologies

EKSHelmCloudflareMCP ServersPrompt Test Manager

Certifications & Qualifications

SOC 2 ComplianceISO 27001 Compliance

Industry Keywords

Infrastructure EngineeringDevOpsSREAccess ManagementMulti-Region Resilience

Tech Stack

Tools & technologies

AnsibleAWSCloudDjangoDNSKubernetesLinuxPostgresPythonTerraform

About the role

Key responsibilities & impact

Join the two-person DevOps team running all of 15Five's infrastructure
Own cloud infrastructure, databases, CI/CD, reliability, security operations, and the growing AI platform
Design, build, secure, troubleshoot, provision, scale, upgrade, and optimize AWS and EKS/Kubernetes infrastructure using Terraform and Helm
Provide infrastructure and systems architecture input for security, scalability, reliability, and performance
Run PostgreSQL upgrades, backups, restore tests, and performance tuning
Build and improve CI/CD 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 maintain email and domain security
Deploy and secure MCP servers, LLM integrations, and agent frameworks
Build AI workflow automations and manage prompts, skills, and evaluations in Prompt Test Manager
Enforce least-privilege access, track AI usage and spend, help shape AI policy, and administer AI tools across the company
Maintain Ansible for user access and server configuration and automate repeatable work
Resolve requests from engineering and business teams, including internal systems, vendor integrations, and access provisioning
Scope and deliver infrastructure, operations, and AI projects
Maintain runbooks and Guru documentation
Collaborate with engineering squads, IT, security, and business teams
Review infrastructure changes, run incidents end to end, lead disaster recovery or restore tests, and deliver major reliability, security, or cost projects

Requirements

What you’ll need

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 production Kubernetes; EKS preferred
Infrastructure as code with Terraform; Terragrunt a plus; 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
Hands-on on-call and incident response experience
PostgreSQL administration, including upgrades, backups, restores, and performance tuning
Practical security operations, including IAM, 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, including 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
Cloudflare, DNS, and email security including SPF, DKIM, DMARC, and 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
Full-time Monday-Friday availability during regular business hours, plus shared weekly on-call rotation with scheduled after-hours coverage
Occasional early-morning or evening meetings for US and EU teammates
Must verify identity and eligibility to work in the United States

Benefits

Comp & perks

Medical, dental, and vision insurance with 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
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 wellbeing offerings
Work with experts in leadership, culture, and personal development
Flexible regular business hours
Global collaboration with US and EU teammates