Executive Assistant

Executive Assistant

Location: Pittsburgh, PA

Salary: $65,600-$77,650

About Gray Swan

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.

Learn more about how we work

The Role

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.

What You’ll Do

• 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.

Who You Are:

• 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.

Bonus Points If You Have

• 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.

You’ll Thrive Here If You

• Love working adjacent to technical teams– you will learn so much about AI safety through osmosis in this role!

• Are looking for a role where you have a huge opportunity to work hard, prove yourself, and build your skillset by trying new things and learning on the job.

• Are excited about the prospect of working with an AI startup that is growing quickly

Compensation & Benefits

We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.

Salary: $65,600-$77,650

Equity: Competitive equity package

Benefits:

• 401k with up to 4% matching

• 28 days annual leave (vacation + holidays)

• Health, dental, and vision coverage

• Catered lunches (Pittsburgh office)

• Flexible work arrangements

• Visa sponsorship available for exceptional candidates

Interview Process

Application review . We read everything; we’ll respond within 14 business days.

Experience & culture interview (60 min). Conversational exploration of the skills fit.

Executive Interview (30 min)

Reference checks . We’ll reach out to 3-5 references that you provide.

Offer . If it’s mutual, we move fast.

How to Apply

Application and Video Submission In lieu of a phone screen, please submit a video cover letter, no longer than two minutes maximum , explaining why you are the right candidate for this role. Should you need accommodation, please contact [email protected].

Compensation Range: $65,600 - $77,650