Deployment Strategist

This role is ideally based in Oahu, HI, with some flexibility for candidates located in San Diego, CA, with understanding that the San Diego location may require more frequent travel.

If you're not located in or near Oahu, HI or San Diego, CA you must be willing to relocate (with assistance from the Onebrief).

Onebrief is a revolutionary platform for military staff workflows and operational planning. The software is designed to enable smarter, real-time decisions. With unparalleled collaboration features, AI-enhanced tools, and customizable workflows, Onebrief makes staffs superhuman. The expanding roster of customers includes COCOMs and Service Components worldwide.

Founded in 2019 by a group of experienced planners, today, Onebrief’s workforce of 120+ spans veterans from all forces and global organizations, and technologists from leading-edge software giants. Onebrief’s growth is exemplary, having raised $53M+ and counting from leading venture investors.

We’re hiring a Deployment Strategist to support the deployment of Onebrief’s operational planning platform across U.S. military environments. This is a technical, external-facing role focused on enabling fast, secure, and successful implementations in high-stakes settings.

You’ll work closely with our Platform Engineering, Sales, and Customer Relations teams to design solutions, guide stakeholders through technical hurdles, and deliver the system in a way that builds long-term trust. From discovery to accreditation to go-live, you’ll be a key force in bringing Onebrief to life on real-world missions.

You’re a systems-minded engineer who can navigate both technical depth and human nuance. You know how to design for real-world constraints and explain your thinking clearly to a range of stakeholders, from platform engineers to government leads.

You thrive in ambiguous environments and bring a calm, solutions-oriented approach when the path forward isn't obvious. You care about outcomes, not just execution, and you're comfortable leading without needing to be the loudest voice in the room.

• Deployment Engineering Lead the technical delivery of new Onebrief deployments, including infrastructure setup, network planning, and environment configuration.

• Technical Discovery Guide solution discovery and scope definition alongside Sales and Platform, especially for multi-network or constraint-heavy environments.

• Accreditation Support Complete or support the creation of technical artifacts required for Authority to Operate (ATO) and related workflows.

• Stakeholder Alignment Partner with customer engineers and leadership to unblock deployments, explain tradeoffs, and build shared understanding.

• Collaboration Work with internal teams to turn deployment requirements into sustainable productized workflows and delivery plans.

Clearance & Location Requirements

• Must hold an active Top Secret clearance with SCI eligibility

• Willing to travel up to 50%, especially if not based in Oahu or San Diego

Technical Expertise

• 7+ years in a software or data engineering role, ideally with experience in deployment-heavy or regulated environments

• Deep experience with cloud platforms (AWS, Azure, or GCP) and infrastructure-as-code tools (Terraform or Pulumi)

• Proficiency with Kubernetes, Postgres, secure networking, and automation tooling

• Track record of scaling infrastructure and improving performance across multiple environments

Deployment & Delivery Experience

• Led cross-functional technical workstreams from discovery through delivery

• Worked on or adjacent to compliance efforts (e.g., FedRAMP, ATOs, Zero Trust design)

• Skilled in framing project scope and sequencing work to balance urgency with sustainability

Communication & Collaboration

• Clear and confident communicator, both in writing and in person

• Comfortable navigating distributed teams and async collaboration

• Brings a team-first, low-ego approach to solving problems

Bonus Skills (Nice to Have)

• Experience in government, defense, or other high-trust technical environments

• Certifications like AWS/GCP/Azure, Sec+, or Linux Foundation CKA/CKAD

• Background in both data and DevOps engineering

This role puts you at the front line of deploying software that transforms how military staffs operate under pressure. You'll work on real networks, solve real infrastructure challenges, and see your work come to life in environments where clarity, reliability, and speed genuinely matter.

Onebrief is post-product-market fit and already trusted in mission-critical settings. We’re profitable, growing intentionally, and focused on high-quality delivery, not bloated headcount. If you want to shape deployments that scale, and be part of a team that values system thinking and shared ownership, you’ll feel right at home here.

Compensation Range: $190K - $220K