Executive Assistant

Gray Swan AI•Pittsburgh, PA

9h•$65,600 - $77,650•Onsite

About The Position

Gray Swan protects organizations from emerging AI security threats. We build real-time threat detection, automated validation, and adaptive defenses for AI labs and enterprises. We’re a team of ~25 people, well-funded, and growing fast. As an Executive Assistant, you will own the communication, collaboration, and day-to-day execution that keep our executive team focused on the highest-impact work. You’ll be our executive engine, always propelling us forward: managing calendars and communications with precision, preparing leaders for high-stakes meetings, and proactively managing and triaging critical executive tasks. Your work directly shapes how quickly decisions get made and how smoothly the company operates. This is a hands-on, high-trust role with real influence and room to grow alongside the company. If you’re highly organized, move quickly, and are motivated by making strong leaders even more effective — while being comfortable speaking up when needed — we’d love to hear from you.

Requirements

You have 5+ years of experience supporting senior leaders or executives in a fast-paced environment. Candidates with 8+ years of experience may be considered for a Senior Executive Assistant level
You’re an exceptional written communicator and are comfortable drafting, editing, and sending messages on behalf of executives with clarity and good judgment.
You have a proven track record of managing complex, multi-calendar schedules and keeping priorities aligned as contexts shift.
Create and coordinate travel itineraries to optimize for efficiency and impact.
You operate with high discretion and trust, and you’re comfortable handling sensitive or confidential information.
Can cut through the noise and get things done when others have stalled in decision making.
You create forward motion in environments with competing priorities.

Nice To Haves

Experience supporting founders or C-suite executives at a startup or high-growth company.
Have provided strategic business support or advice to executives
Hands-on experience managing executive inboxes at scale, including drafting responses and setting communication norms.
Experience using tools like Google Workspace (Gmail, Calendar, Docs), Slack, and modern task or project-tracking tools.
If you don’t meet 100% of these requirements, you should still seriously consider applying. We care more about what you can do than your credentials.

Responsibilities

Own executive inbox management. Triage incoming messages, draft and send responses on behalf of executives, and ensure communication is timely, clear, and aligned with priorities.
Elevate written communication for leadership. Edit, structure, and draft executive emails and updates so messages are concise, well-reasoned, and easy for recipients to act on.
Manage complex executive calendars with precision. Coordinate multiple calendars, resolve conflicts, and ensure time is allocated to the highest-impact meetings and commitments.
Enable effective collaboration between the executive team and the broader organization. Act as the connective tissue between the C-suite and the rest of the company by ensuring meetings are purposeful, context is shared in advance, decisions are clearly documented, and follow-through is aligned and executed.
Prepare executives for key meetings. Compile agendas, background context, and follow-ups for internal, customer, and external conversations to support effective decision-making.
Establish and maintain executive operating rhythms. Implement lightweight workflows, templates, and norms that keep communication and scheduling consistent and efficient.