15Five

15Five

15Five offers a continuous performance management platform that enhances employee engagement and productivity through integrated tools for feedback, objective tracking, and recognition, enabling managers to foster open communication and address workpla...

Professional Services
11-50
Founded 2011
$94M raised

Description

  • Design, build, secure, troubleshoot, and optimize AWS and EKS/Kubernetes infrastructure using Terraform and Helm.
  • Provide infrastructure architecture guidance focused on security, scalability, reliability, and performance.
  • Manage PostgreSQL upgrades, backups, restore testing, and performance tuning.
  • Build and improve CI/CD pipelines and release engineering practices.
  • Own Datadog observability and alerting, participate in scheduled after-hours on-call coverage, respond to incidents, and lead post-incident reviews.
  • Maintain and test disaster recovery, backups, and failover plans.
  • Manage access, secrets, vulnerability patching, Cloudflare networking, VPN, and email/domain security while supporting audits.
  • Deploy and secure AI infrastructure, including MCP servers, LLM integrations, agent frameworks, prompts, evaluations, and AI workflow automations.
  • Maintain Ansible configuration management and automate repeatable operational work.
  • Scope and deliver infrastructure, security, reliability, cost, and AI projects while maintaining documentation and runbooks.

Requirements

  • 5+ years of experience in DevOps, SRE, or infrastructure engineering; 3+ years for the DevOps Engineer II level.
  • Hands-on experience with AWS, Linux, and production Kubernetes; EKS experience preferred.
  • Experience with Terraform, Terragrunt preferred, Helm, Helmfile, and infrastructure as code.
  • Experience building and maintaining CI/CD pipelines and Git-based workflows.
  • Configuration management experience with Ansible.
  • Strong Python and/or Bash scripting skills.
  • Experience with Datadog or similar monitoring tools, on-call rotations, and incident response.
  • PostgreSQL administration experience, including upgrades, backups, restores, and performance tuning.
  • Practical security operations experience with IAM, secrets, patching, and network configuration.
  • Clear communication skills and the ability to own projects end to end on a small team.
  • Experience with AI tooling, governance, access controls, usage and cost tracking, or prompt evaluation pipelines preferred.
  • Familiarity with Cloudflare, email security, SOC 2 or ISO 27001 audits, disaster recovery, Django, or distributed US/EU teams preferred.
  • Availability for Monday–Friday business hours, shared weekly on-call coverage, and occasional early or evening meetings.

Benefits

  • Remote work with flexible business hours.
  • Medical, dental, and vision insurance with employer subsidy.
  • Employer-paid short- and long-term disability and term life insurance.
  • Mental health and wellness resources, family planning support, and an inclusive benefits stipend.
  • Flexible time off, paid company holidays, military leave, sabbatical program, and generous parental leave.
  • 401(k) with 4% employer matching after six months.
  • Opportunities to work with experts in leadership, culture, and personal development.

Interested in this position?

Apply directly on the company website

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