Staff Outcome Designer

Onebrief

5d • $185,000 - $230,000 • Remote

About The Position

Onebrief builds collaboration and AI-powered workflow software for military planning and operational coordination. Military planning is complex by nature, requiring teams to coordinate information, people, and decisions across systems and locations. Onebrief brings planning, collaboration, simulation, and AI into one connected environment, helping teams test strategies, adapt to changing conditions, and make decisions with greater clarity when the stakes are real. We are a distributed team of builders from military, operational, and technology backgrounds who care deeply about improving how important work gets done. Some team members work remotely, while others work directly alongside customers in operational environments around the world. Founded in 2019, Onebrief is backed by leading investors including General Catalyst, Battery Ventures, Insight Partners, Sapphire Ventures, and Human Capital. Valued at more than $2 billion, we continue to invest in product innovation, AI capabilities, and team growth.

Design at Onebrief is capacity-constrained in a way engineering increasingly isn't. Agents have changed what's possible for production velocity, but the design team doesn't yet have the systems to ship at that same speed and scale. This role exists to build those systems. Your job isn't to design faster yourself. It's to build the platform that removes capacity as the constraint for the rest of the design team: the agentic design system platform, the tools and utilities designers rely on day to day, and the services that support design needs across the company at scale, including automated intake and evaluation, release QA, and telemetry from production environments. You're building the engine that drives the design flywheel. The faster and more reliable that engine is, the faster the whole team ships good work, and the more data comes back to make the engine better.

Beyond the platform, this role also leads moonshot projects on the future of agentic experiences for our customers. This includes exploring forefront agentic technology being developed in the private and defense sectors and leading how Onebrief translates what's possible into what's next. This role is deliberately built to cross traditional boundaries between design roles. On moonshot work, you lead directly and pull in Product Designers, Design Engineers, or anyone else needed, without a fixed technical/product split.

This is a high-agency, ambiguous-problem role. There's no existing playbook to follow. You're writing it.

Requirements

• Deep, hands-on experience building and scaling agentic design systems, including automated documentation, syncing code and design sources of truth, governance systems, visual linting/auditing, automated reviews, and designer utilities (plugins, agent skills, MCPs).
• Experience building production/release infrastructure such as automated pipelines, intake/evaluation systems, QA automation, or telemetry.
• Familiarity with deployment processes and stacks such as Docker, EKS (Kubernetes on AWS), and GitHub CI/CD pipelines, or comparable.
• Informed opinions on where and how human gates should exist versus where automation is most effective, with the ability to defend that judgment with examples.
• Track record leading ambiguous, cross-functional exploratory or moonshot projects, pulling in whoever's needed regardless of role boundaries and turning exploration into something real.
• Comfortable being the first and only person in a role, building the playbook rather than inheriting one.

Nice To Haves

• Active, contributing member of the design systems community (writing, speaking, open source, or comparable).
• Experience with knowledge graphs, vector stores, or other semantic infrastructure for agent context/memory.
• Familiarity with eval/validation frameworks for agentic outputs, beyond "vibes."
• Curiosity about and exposure to forefront agentic technology in the private or defense sectors, and comfort exploring unproven, emerging tools and approaches.

Responsibilities

• Architect and build the agentic design system platform, including components, patterns, documentation, and utilities (MCPs, skills, plugins) that Product Designers and Design Engineers build on.
• Build intake and automated evaluation systems that triage incoming design requests and contributions and check them against standards automatically.
• Build release QA automation that catches quality and consistency issues before they ship.
• Build data telemetry from production environments, creating feedback loops that show whether shipped design work is actually performing as intended and route that signal back into the platform.
• Lead moonshot projects exploring the future of agentic customer experiences, drawing on forefront technology from the private and defense sectors and pulling in whoever's needed across design and engineering to make them real.
• Make deliberate, defensible calls on where human review gates belong versus where automation should own the decision.
• Work within Onebrief's deployment stack (Docker, EKS/Kubernetes on AWS, GitHub CI/CD pipelines) to ship and maintain these systems reliably.
• Participate in team reviews and provide meaningful, platform-informed input to the Head of Department on strategic initiatives and the design team's roadmap.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed