Executive Assistant to the General Counsel

About this role

GC AI https://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) https://gc.ai/blog/gc-ai-raises-60-million-series-b-to-give-every-company-a-legal-advantage, 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

The General Counsel at GC AI operates as a true hybrid executive: part legal leader, part business operator. This role touches legal, HR, talent, security, compliance, finance, and executive leadership on any given day.

We're looking for a sharp, organized recent graduate who can be a true force multiplier for someone who runs at this pace. You'll own the operational backbone of one of the busiest seats in the company, working across a wide and constantly evolving set of priorities. This is an exceptional opportunity for someone early in their career who thrives in fast-paced environments and wants to learn the inner workings of a high-growth legal tech company from the inside.

Chicago is our preferred location for this role. GC AI intends to open a Chicago-area office within the next two years, and this person will play an integral role in standing up that presence.

This is a high-trust, high-context role. You will be exposed to confidential legal matters, compensation data, hiring decisions, personnel issues, outside counsel communications, and board-level information. Discretion is non-negotiable.

WHAT YOU'LL DO

- Calendar and scheduling: Manage a complex, high-volume calendar across Eastern to Pacific time zones with 12+ daily meetings. Prioritize, protect focus time, resolve conflicts, and coordinate across internal and external stakeholders. Become fluent in Reclaim.ai http://Reclaim.ai scheduling logic and other booking flows.

- Meeting operations: Prepare agendas and briefing materials for recurring leadership meetings (Exec, G&A Leadership, Legal Team Sync, Pricing Standup, Talent Team, HR Biweekly). Track action items from Granola meeting notes and ensure follow-through.

- Travel coordination: Book flights, hotels, and ground transportation for regular domestic travel.

- Communication triage: Monitor and triage Slack messages and email across 10+ active channels spanning legal, HR, recruiting, pricing, and deal support. Flag time-sensitive items, draft initial responses where appropriate, and ensure nothing falls through the cracks.

- Recruiting and hiring support: Coordinate interview scheduling through Ashby. Prepare interview briefings, manage candidate communications, and support onboarding logistics using the Notion.

- Project and task tracking: Maintain and update project trackers in Notion (legal, HR, RevOps). Track deliverables and deadlines across Asana. Keep the GC's personal task list current.

- Outside counsel and vendor coordination: Schedule and prepare for calls with external law firms and vendors (privacy counsel, compensation consultants, compliance vendors). Manage engagement logistics, coordinate document sharing, and assist with tracking billing and invoicing.

- Compensation and HR administration: Support comp cycle logistics, EEO-1 reporting preparation, benefits administration coordination, and HRIS workflows. Handle sensitive personnel documents with appropriate confidentiality.

- Document and information management: Organize and maintain files in Google Drive, prepare Google Docs and Sheets for internal reviews, and ensure version control across workstreams.

- Expense and administrative support: Process expense reports, manage subscriptions and vendor accounts, coordinate office/workspace logistics, and handle other day-to-day administrative needs.

WHAT WE'RE LOOKING FOR

- Bachelor's degree (recently completed or expected) and prior office, internship, or administrative experience in a professional environment; while helpful to have prior EA experience, this is a great opportunity for a new highly organized graduate!

- Ability to manage a high-volume, fast-moving calendar with competing priorities across time zones

- Strong proficiency with Google Workspace (Calendar, Docs, Sheets, Drive, Gmail), Slack, and Notion

- Experience with or ability to quickly learn: Reclaim.ai http://Reclaim.ai, Ashby (or similar ATS), HubSpot, Granola, Zoom, Asana, Notion and, most importantly, GC AI!

- Exceptional written communication skills, including the ability to draft Slack messages, emails, and internal communications in a professional, concise tone

- Maturity and professionalism to handle highly confidential information: legal strategy, personnel matters, compensation data, outside counsel communications, and executive decision-making

- Natural organizational instincts: you track details without being asked, follow up proactively, and close loops

- Good judgment about when to act independently and when to escalate

- Chicago-based strongly preferred; some travel to the San Mateo, CA headquarters and for offsites expected

NICE TO HAVE

- Internship or work experience in a legal…