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.

Who You Are:

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 careers@grayswan.ai.

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