AI Chief of Staff

GC AI

18d • $175,000 - $275,000 • Hybrid

About The Position

GC AI is the fastest-growing and most trusted legal AI platform for in-house legal teams. We're building the future of legal work, and we're doing it fast. You'll join at a pivotal moment—when decisions matter, impact is immediate, and the runway to shape your career is wide open. We’re a high-performing team where you'll have real ownership and influence from day one.
More than 1,800 companies use GC AI to drive their business forward, including 150+ public companies, 25+ unicorns, and brands such as News Corp, Miro, Bass Pro Shops, Snyk, Skims, Liquid Death, Vercel, Zscaler, and TIME.
We've 10x'd revenue in 12 months, raised a $60 million Series B ($555 million valuation), and are growing faster than ever. We are backed by incredible investors, including Scale Venture Partners, Northzone, Sound Ventures, and Guillermo Rauch, CEO of Vercel.
If you thrive when the stakes are high and the path isn't paved, you'll love it here. Our six guiding principles are: 1% better every day, customer obsession, ship today, find a way, care deeply, and own it completely. Come shape the future of legal work with us.
About The Role
You'll own the internal AI infrastructure that makes our team unreasonably fast. That means building, evaluating vendors, and continuously evolving the AI systems our team runs on, with the goal of maximizing every person's clock speed and scaling our ability to deploy agents across the business.
You'll sit at the intersection of engineering, operations, and strategy, building the internal tools, workflows, and AI-powered systems that eliminate manual work across Sales, Marketing, Customer Success, Finance, Legal, People Ops, and Product.
If you’ve ever wanted to build the “agent operating system” inside one of the fastest-growing AI infrastructure startups, this is your shot.

Requirements

• A technical practitioner. You understand how models actually work, not just API calls, but attention, context windows, inference tradeoffs, tool use patterns. You read papers. But your first instinct is always to build, not to theorize. You've shipped real systems that automate real work.
• Someone with battle-tested opinions on AI-assisted development. You've pushed vibe coding techniques far enough to know where they break. You have strong, experience-driven opinions about what works and what doesn't, grounded in first principles. You know when to let the model drive and when to take the wheel.
• An automation obsessive. You've already automated your own life to a degree that others find somewhat unhinged. You see manual processes the way most people see bugs, something that shouldn't exist and won't for long.

Responsibilities

• Build agentic infrastructure that spans the full company.
• Own the company's AI tooling strategy: evaluate vendors, make build-vs-buy decisions, implement tools, and drive adoption.
• Design and deploy internal applications using modern AI coding tools (Claude Code, Cursor, Replit) that solve real workflow problems for non-technical teams.
• Create and maintain integrations across the company's core systems (CRM, HRIS, project management, communication tools).
• Run office hours and training sessions to drive adoption, and create documentation (Loom walkthroughs, written guides) so teams can self-serve.
• Establish governance frameworks for AI tool usage, data handling, and security across the org.

What This Job Offers

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