Executive Assistant to the CEO

GC AI

GC AI

Administration

San Mateo, CA, USA

Posted on May 6, 2026
Executive Assistant to the CEO
San Mateo, California
Executive Assistant
Hybrid
Full-time
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 1,500 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.

Location

We are hiring for this role to be based out of our San Mateo, CA office. Our team works in-office on Mondays, Wednesdays, and Fridays.

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.


Compensation

GC AI's compensation package includes a competitive base salary benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits, as well as commission plans for applicable roles. Our US-based compensation range for this role is $120,000 – $180,000. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors.
These compensation bands are just the starting point. After someone joins and proves they’re and exceptional performer, we adjust quickly to ensure their compensation aligns with their impact.
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
Fraud Notice to GC AI Applicants
To protect yourself against phishing and recruitment fraud, please note that GC AI only accepts job applications through our official careers page at https://gc.ai/careers and through sponsored jobs on LinkedIn. All legitimate communication from our team regarding job opportunities will come from a GC AI team member with a @gc.ai or @getgc.ai email address.
GC AI will never:
  • Refer you to external websites to apply
  • Conduct interviews over email, chat platforms, or messaging apps
  • Ask you to provide payment or purchase equipment
  • Request personal or financial information such as your mailing address, social security number, credit card numbers, or banking information during the application process
Examples of fraudulent email addresses:
  • info.gcai.careers.com@gmail.com
  • info.gc.aicareers.online.com@gmail.com
  • Any email address ending in @gmail.com, @yahoo.com, or other free email services
If you are contacted by someone claiming to be from GC AI via an unofficial channel or from a suspicious email address, please do not share any information. Mark the communication as "phishing" or "spam" and do not respond.
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Req ID: R113
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