Principal Infrastructure Engineer

About Onebrief 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 $320m+ from top-tier investors, including Battery Ventures, General Catalyst, Sapphire Ventures, Insight Partners, and Human Capital, and today, Onebrief is valued at $2.15B. With this continued growth, Onebrief is able to make an impact where it matters most. About the Role We are hiring a Principal Infrastructure Engineer to lead the next evolution of Onebrief’s infrastructure. This role owns the long-term health, scalability, and technical direction of the platform. You will look beyond the current delivery cycle to anticipate the infrastructure needs of mission-critical applications operating across multiple air-gapped environments. You are a strategic engineer who translates complex Department of War (DoW) constraints into a cohesive technical roadmap. Your work will enable product and engineering teams to deliver reliably across multiple classification levels with minimal friction. About You You are a strategic planner who excels at technical roadmapping and can identify architectural gaps early, then build multi-quarter plans to address them before they become constraints. You think in systems, looking beyond individual tickets to understand and redesign the underlying infrastructure. When a pipeline fails, you focus on eliminating the class of failure rather than applying a temporary fix. You take a pragmatic approach to technology decisions, knowing when to adopt new tools and when to invest further in proven systems. You value long-term maintainability and operational clarity over short-term optimizations. You lead by example, raising the technical bar through clear design documents, high-quality reviews, and mentorship on complex systems design. What You Will Do • Define and execute a one- to two-year technical vision for Onebrief’s infrastructure in partnership with engineering leadership • Design and evolve a deployment strategy focused on AWS and on-prem environments, with support for partner-hosted deployments in other cloud platforms as required • Build security and compliance directly into the infrastructure lifecycle through automation and policy-driven systems • Identify and resolve the most complex technical debt and performance bottlenecks affecting the broader Product and Eengineering organizations • Design and lead the implementation of the next generation of the Onebrief’s platform infrastructure Qualifications • 10+ years of hands-on experience building and scaling infrastructure systems • 5+ years of experience in Platform Engineering, DevOps, or Site Reliability Engineering • Proven experience leading organization-wide infrastructure initiatives and executing roadmaps aligned with business objectives • Deep experience operating in highly regulated, secure, and/or air-gapped environments, including the Department of War or the Intelligence Community • Expert-level knowledge of Kubernetes, including multi-cluster design, security, and the broader CNCF ecosystem • Experience designing enterprise-grade infrastructure-as-code and automation frameworks using tools such as Terraform or Ansible • Proficiency in Python and Bash for building custom tooling and automation • Ability to communicate complex technical strategies to engineers and stakeholders and build alignment around long-term architectural decisions • Willingness to obtain and maintain eligibility for a Top Secret clearance with SCI Notice to Third Party Recruitment Agencies Please note that Onebrief does not accept unsolicited resumes from recruiters or employment agencies. In the absence of an executed Recruitment Services Agreement, there will be no obligation to any referral compensation or recruiter fee. In the event a recruiter or agency submits a resume or candidate without an agreement Onebrief explicitly reserves the right to pursue and hire those candidate(s) without any financial obligation to the recruiter or agency. Any unsolicited resumes, including those submitted to hiring managers, shall be deemed the property of Onebrief. Apply tot his job Apply To this Job