AI Chief of Staff

GC AI

$150K — $200K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience in AI infrastructure or related field
  • Strong understanding of AI model mechanics and development processes
  • Experience in building automation systems and internal tools
  • Proven track record of evaluating vendors and implementing software solutions
  • Ability to design and deliver effective training and documentation

Responsibilities

  • Build and maintain infrastructure for AI across the organization
  • Drive the AI tooling strategy: vendor evaluation and implementation
  • Design internal applications using AI coding tools for non-technical teams
  • Create integrations across core company systems like CRM and HRIS
  • Lead training sessions to promote tool adoption and self-service documentation
  • Establish governance frameworks for AI usage and data security

Benefits

  • Remote work with a hybrid option for local employees
  • Opportunity to shape the future of AI in a fast-paced startup environment
  • Ownership over impactful projects that streamline operations
  • Collaborative environment at the intersection of technology and business strategy
  • Access to cutting-edge AI tools and resources
Full Job Description
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.

What You'll Do
  • 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 We're Looking For
  • 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.
A Note On Pace

We're building something new in a once-in-a-generation shift in technology and the legal industry, so we move at a relentless pace. We expect urgency, ownership, and good judgment even when things aren't perfectly clear. If you need structure and consensus to do your best work, this isn't the right place for you. If you thrive in ambiguity and growth, work with intensity, and want real responsibility, keep reading. We're excited to meet you.

A Note On Pace

We're building something new in a once-in-a-generation shift in technology and the legal industry, so we move at a relentless pace. We expect urgency, ownership, and good judgment even when things aren't perfectly clear. If you need structure and consensus to do your best work, this isn't the right place for you. If you thrive in ambiguity and growth, work with intensity, and want real responsibility, keep reading. We're excited to meet you.

Location Policy

This is a remote role unless you fall within the following parameters. If you live within approximately 50 miles of our San Mateo, CA or Provo, UT office, the position follows a hybrid schedule with in-office days on Tuesdays, Wednesdays, and Thursdays.

Similar Jobs

More Jobs at GC AI

More Enterprise Technology Jobs

Find similar AI Chief of Staff jobs: