Executive Assistant to the General Counsel

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 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, 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 department, law firm, or professional services environment

Familiarity with legal tech, AI/ML products, or SaaS companies

Experience supporting or working closely with senior leaders in any capacity

Prior experience managing local office operations

Energized by a startup environment where scope expands and roles evolve quickly

Skills Required
Bachelor's degree (recently completed or expected) and prior office, internship, or administrative experience in a professional environment
Ability to manage a high-volume, fast-moving calendar across time zones (Eastern to Pacific)
Strong proficiency with Google Workspace (Calendar, Docs, Sheets, Drive, Gmail), Slack, and Notion
Experience with or ability to quickly learn Reclaim.ai, Ashby (or similar ATS), HubSpot, Granola, Zoom, Asana, Notion, and GC AI
Exceptional written communication skills; ability to draft professional, concise Slack messages, emails, and internal communications
Maturity, professionalism, and strict discretion handling highly confidential legal, personnel, and compensation information
Natural organizational instincts: proactive follow-up, detail tracking, and closing loops
Good judgment to act independently when appropriate and escalate when necessary
Willingness/ability to travel to San Mateo, CA for offsites and occasional in-person meetings
Chicago-based strongly preferred
Support recruiting and onboarding logistics using Ashby and Notion