Executive Assistant to the CEO

GC AI; United States; Hybrid; USD 90,000 - 130,000; Full time

Job summary

GC AI is seeking an experienced Executive Assistant to support the CEO as her operational right hand. You will manage calendars, travel, communications, and office operations while maintaining high discretion and precision.

This role requires frequent travel with the CEO, strong writing, and the ability to move quickly in a fast-paced startup environment. GA-ready and AI-forward mindset preferred.

Qualifications

• 3+ years of experience as an Executive Assistant, Chief of Staff, or similar operator supporting executives at startups.
• AI-native: you use AI tools daily and look for ways to improve your work.
• Detail-oriented and fast; you notice typos and ensure accuracy.
• High discretion: you handle confidential information professionally.
• Strong operator: manage priorities, follow through, and communicate proactively.
• Excellent writing: draft concise communications in active voice.

Responsibilities

• Own the CEO’s calendar: schedule, protect focus time, prioritize, and align time with high-impact work.
• Serve as the CEO’s communication hub: triage Slack/email, draft responses in her voice, track next steps.
• Coordinate travel logistics and travel with the CEO to events and meetings.
• Drive meeting operations: set agendas, prep materials, ensure context and Zoom links, take notes, track follow-ups.
• Support initiatives with research, data analysis, progress tracking, and clear summaries for faster decisions.
• Run the San Mateo office: greet visitors, prep rooms, keep space tidy, collaborate with the workplace manager.
• Build lightweight systems to reduce CEO drag and speed the company.

Skills

Executive support

AI-native

Attention to detail

Discretion

Operations

Strong writing

Travel readiness

Tools

Zoom

Slack

Google Suite

HubSpot

DocuSign

Asana

Job description

GC AI is the legal AI platform built for in-house legal teams. Your decisions shape the product, your impact is immediate, and you own your work from day one.

More than 2,000 companies run their legal work on GC AI, including 200+ public companies, 25+ unicorns, and teams at News Corp, Nestlé, Miro, Bass Pro Shops, Snyk, Skims, Liquid Death, Vercel, Zscaler, and TIME. The platform holds an 80 NPS, more than double the B2B SaaS industry average, which is why GC AI is the leading legal AI platform for companies of all sizes.

GC AI doubled ARR in six months. We raised a $60 million Series B at a $555 million valuation in November 2025 and won #1 Highest Customer Satisfaction at the 2026 SaaS Awards. Our investors include Scale Venture Partners, Northzone, Sound Ventures, and Guillermo Rauch, CEO of Vercel.

You’ll define how things get built, not follow someone else’s playbook. Six principles guide how the team works:

• 1% Better Every Day: small, compounding improvements across everything you ship.
• Customer Obsession: start with the customer and work backward.
• Ship Today: bias toward action and iteration over perfection.
• Find a Way: resourcefulness and ambition over constraint.
• Care: be direct, like an honest friend, even when it’s uncomfortable.
• Own It: full accountability, proactive communication, and attention to detail.

About the Role

You’ll work directly with the CEO and Co-founder as her operational right hand, managing everything from calendar and travel to meeting prep, communications, and office operations.

This is a high-visibility role for someone who is fast, precise, highly discreet, and energized by working closely with a founder who moves quickly, communicates directly, and cares deeply about details. Your ability to anticipate needs, bring order to ambiguity, and keep the CEO focused on the highest-impact work will directly affect how quickly we scale.

Travel with the CEO is a regular part of the job.

What You’ll Do

• Own the CEO’s calendar: schedule meetings, protect focus time, manage competing priorities, and make sure her time maps to the highest-impact work.
• Serve as the CEO’s communication hub: triage Slack and email, surface what needs attention, draft responses in her voice, and track next steps through completion.
• Coordinate travel logistics and frequently travel with the CEO to provide real-time support at conferences, investor meetings, offsites, and other events.
• Drive meeting operations: set agendas, prepare briefing materials, ensure every meeting has the right context and Zoom link, take notes, and track follow-ups.
• Support key initiatives with research, data analysis, progress tracking, and clear summaries that help the CEO make faster decisions.
• Run the San Mateo office: greet visitors, prep meeting rooms, keep the space tidy and high-functioning, and collaborate with the workplace manager once hired.
• Build and improve lightweight systems that reduce CEO drag, create clarity, and help the company move faster.

What You’ve Done

• 3+ years of experience as an Executive Assistant, Chief of Staff, or similar operator supporting executives at startups.
• AI-native: you use AI tools daily and are always looking for new and simpler ways to improve your work.
• Detail-oriented AF. We mean it. You spot typos, ace tests, move fast, and do it in a way that makes others marvel.
• A natural anticipator with high discretion: you see what’s needed and handle it before being asked, you come with recommendations rather than just questions, and you treat confidential information with absolute professionalism.
• An excellent operator: you manage competing priorities, follow through without reminders, communicate proactively when things change, and keep important work from falling through the cracks.
• A strong, clean writer: you draft concise communications in active voice, catch errors others miss, and take pride in the craft of clear writing.
• Willing and able to travel frequently on short notice with the CEO to conferences, investor meetings, offsites, and other events.

Nice to Have

• Experience supporting a CEO, founder, or senior executive at a high-growth startup.
• Experience wearing multiple hats across operations, events, office management, or founder support.
• Proficiency with Zoom, Slack, Google Suite, HubSpot, DocuSign, and Asana.
• Comfort operating in Slack-heavy, AI-forward, high-urgency environments.

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.

How We Work Together

GC AI is a distributed company with team members across North America, and soon Europe. We believe that because our business is AI, human connection matters more, not less. We invest in bringing people together through our hub model: regular coworking sessions, customer dinners, team and company offsites. If you’re in a location without an office, expect up to 10% travel (and more for customer-facing roles).

Team members in the San Francisco Bay Area and Provo, UT (within 50 miles of the office) work together on Tuesdays, Wednesdays, and Thursdays. As we grow, we plan to establish permanent offices in more hub cities, and we will look to our team members to help build that in-person culture. We currently hire across the United States and Canada.

Equal Opportunity Employment

GC AI is an equal opportunity employer that supports workplace diversity and does not discriminate on the basis of race, color, religion, gender identity/expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, physical or mental disability, or any other protected class. GC AI is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities. #LI-GCAI