System Administrator, Hawaii

Onebrief is collaboration and AI-powered workflow software designed specifically for military staffs. By transforming this work, Onebrief makes the staff as a whole superhuman - meaning faster, smarter, and more efficient.

We take ownership, seek excellence, and play to win with the seriousness and camaraderie of an Olympic team. Onebrief operates as an all-remote company, though many of our employees work alongside our customers at military commands around the world.

Founded in 2019 by a group of experienced planners, today, Onebrief’s team spans veterans from all forces and global organizations, and technologists from leading-edge software companies. We’ve raised $123m+ from top-tier investors, including Battery Ventures, General Catalyst, Insight Partners, and Human Capital, and today, Onebrief is valued at $1.1B. With this continued growth, Onebrief is able to make an impact where it matters most.

We are hiring a Systems Administrator (Hawaii) to join our Infrastructure & Security team. This is an operational role focused on day-to-day reliability and secure operations across on-premise DoD enclaves and AWS environments.

You’ll report to our Director of Infrastructure and work closely with SREs, security, and customer success. The role is operational with clear ownership; you’ll keep environments healthy, document what works, and raise issues early so the team can move fast without surprises.

This role requires regular on-site work at customer locations in Hawaii.

Oahu, HI. Within commuting distance to Camp H.M. Smith and Joint Base Pearl Harbor-Hickam; travel on Oahu as required.

If you are not within commuting distance, you must be willing to relocate (with assistance from Onebrief).

Active TS required; SCI eligibility is a plus.

You take pride in stable systems and clean runbooks. You are the person who patches on time, labels the cables, and leaves things better than you found them. You ask good questions, escalate with context, and keep calm when the pager goes off.

You work well with engineers and non-engineers alike. You are hands-on at the command line, practical about tradeoffs, and diligent about documentation. You prefer clear checklists and steady improvement over heroics.

You will keep our production instances secure, updated, and available. You will do this by:

Own day-to-day admin for Linux servers, VMware, and AWS resources; apply patches, manage users, and keep configuration drift low.

Watch the dashboards, tune alerts, and handle first-line incident response; capture timelines and hand off crisp RCAs to SRE when needed.

Apply STIGs, track remediation plans and milestones, and support RMF evidence collection; keep systems audit-ready without slowing the mission.

Surface trends, capacity needs, and recurring issues; suggest small automations or Ansible playbooks that reduce toil.

• 3+ years in a systems administrator or similar ops role

• Clear written habits; you document, ticket, and close the loop

• Comfortable working on-site with government users and vendors

• Strong Linux administration; shell fluency and basic scripting (Bash or Python)

• Experience with VMware vSphere, virtual networks, and storage

• Familiarity with AWS basics, (EC2, VPC, IAM, S3), and standard monitoring tools

• Understanding of containers and Kubernetes concepts; hands-on is a plus

• Experience with Ansible or similar configuration management is a plus

• Working knowledge of DoD environments, STIGs, and RMF

• Hands-on with hardening, patching, and vulnerability remediation

• DoD 8570.01 baseline certification (Security+ or equivalent) or ability to obtain shortly after hire

• Proven habit of keeping systems backed up, logged, and alerting sanely

• Sound judgment under constraints; you escalate early with options, not just problems

• Comfortable operating in air-gapped or low-connectivity environments

You’ll be the operational backbone for our Hawaii deployments. When staffs plan on SIPR, NIPR, or JWICS, your stewardship keeps systems online, hardened, and trusted.

What makes this role compelling:

• Direct mission impact; your work shows up in daily operations, not just dashboards.

• Broad, hands-on scope across Linux, VMware, and AWS; enough variety to grow without thrash.

• Tight partnership with senior SREs and security; learn resilient patterns and ship small automations that reduce toil.

• Clear ownership in a small, high-trust team; short feedback loops and room to shape runbooks and on-call.

• A stable product with real adoption; we are post–product-market fit and profitable, so you can focus on quality and reliability.

Compensation Range: $140K - $180K