Senior DevOps Engineer

This is a fully remote position, open to applicants in United States.

📋 Description

• Become a key member of the two-person DevOps team responsible for managing all of 15Five's infrastructure.

• Take charge of cloud infrastructure, databases, CI/CD, reliability, security operations, and the expanding AI platform.

• Design, construct, secure, troubleshoot, provision, scale, upgrade, and optimize AWS and EKS/Kubernetes infrastructure utilizing Terraform and Helm.

• Provide architectural insights for infrastructure and systems focusing on security, scalability, reliability, and performance.

• Execute PostgreSQL upgrades, backups, restore tests, and performance tuning tasks.

• Create and enhance CI/CD pipelines that facilitate code deployment to production.

• Oversee Datadog observability and alert management.

• Engage in the on-call rotation, respond to incidents, and lead post-incident analysis.

• Maintain and test backup systems, failover procedures, and disaster recovery strategies.

• Manage access and secret rotation, address vulnerabilities, configure Cloudflare network/VPN, and uphold email and domain security.

• Deploy and secure MCP servers, LLM integrations, and agent frameworks.

• Develop AI workflow automations and manage prompts, skills, and assessments through the Prompt Test Manager.

• Implement least-privilege access, monitor AI usage and expenditures, assist in shaping AI policy, and manage AI tools within the organization.

• Maintain Ansible for user access and server configuration while automating repetitive tasks.

• Address requests from engineering and business teams, including internal systems, vendor integrations, and access provisioning.

• Define and deliver infrastructure, operations, and AI-related projects.

• Keep runbooks and Guru documentation up to date.

• Collaborate effectively with engineering squads, IT, security, and business teams.

• Review infrastructure modifications, manage incidents from start to finish, lead disaster recovery or restore tests, and execute major reliability, security, or cost improvement projects.

⛳️ Requirements

• 5+ years of experience in DevOps, SRE, or infrastructure engineering for Senior; 3+ years for DevOps Engineer II.

• Extensive hands-on experience with AWS and Linux, along with production Kubernetes; EKS preferred.

• Proficient in infrastructure as code using Terraform; experience with Terragrunt is a plus; Helm knowledge is essential.

• Demonstrated experience in building and maintaining CI/CD pipelines.

• Familiarity with configuration management using Ansible.

• Strong scripting abilities in Python and/or Bash, alongside Git-based workflows.

• Experience with monitoring and alerting tools, particularly Datadog or similar platforms.

• Practical on-call and incident response experience.

• Proficient in PostgreSQL administration, encompassing upgrades, backups, restores, and performance tuning.

• Hands-on experience in security operations, including IAM, access management, secrets management, patching, and network configuration.

• Excellent written and verbal communication skills for engaging with both technical and non-technical audiences.

• Capability to manage projects independently from inception to completion within a small team.

• Experience in deploying or securing AI tools, including MCP servers, LLM APIs, agent frameworks, or prompt evaluation pipelines.

• Knowledge of AI governance, including access controls, usage and cost tracking, or acceptable-use policies.

• Familiarity with Cloudflare, DNS, and email security protocols, including SPF, DKIM, DMARC, and MTA-STS.

• Experience in supporting SOC 2 or ISO 27001 audits.

• Knowledge of disaster recovery testing and multi-region redundancy.

• Basic understanding of Django or other Python web applications.

• Experience in supporting distributed teams across US and EU time zones.

• Availability for full-time work Monday through Friday during standard business hours, alongside participation in a shared weekly on-call rotation with scheduled after-hours coverage.

• Willingness to attend occasional early-morning or evening meetings to accommodate US and EU teammates.

• Must confirm identity and eligibility to work in the United States.

🏝️ Benefits

• Medical, dental, and vision insurance with a cost subsidy provided by 15Five.

• Employer-sponsored short-term disability, long-term disability, and term life insurance.

• Family planning support through enhanced medical plans and consultation services.

• Inclusive Benefits Stipend.

• Access to mental health and wellness resources.

• Flexible Time Off Program.

• Generous paid leave policy for new parents.

• Military leave provisions.

• Paid Company Holidays.

• Sabbatical Program.

• 401(k) plan with a 4% matching contribution after 6 months of service.

• Opportunities for remote work.

• Annual discretionary bonus program.

• Equity awards offered.

• Comprehensive wellbeing offerings available.

• Collaborate with experts in leadership, culture, and personal development.

• Regular business hours are flexible.

• Engage in global collaboration with teams across the US and EU.