Executive Assistant (EA)

💼 About the Role

We’re hiring an Executive Assistant to the CEO to act as a force multiplier in a fast-moving startup environment.

This is not a passive support role. This is an execution-heavy role with real ownership, not a prestige EA role. You’ll be trusted with said ownership over recurring responsibilities, sensitive tasks, and ad-hoc requests that need to be handled reliably, quickly, and with judgment. The ideal candidate brings strong initiative, operates with urgency, and treats “this isn’t possible” as a temporary state.

This role is remote and requires exceptional written communication and self-direction.

🧠 What You’ll Do

Own critical tasks end-to-end

• Handle recurring operational tasks (e.g. invoices, payments, follow-ups) with zero drop-off
• Build and maintain your own tracking systems to ensure nothing is missed
• Close loops proactively without reminders
  
  

Move fast and prioritize correctly

• Execute small, urgent tasks immediately and return concise, decision-ready outputs
• Avoid overwork and over-documentation when speed is required
• Switch seamlessly between fast execution and deeper research depending on the task
  
  

Act with agency

• Anticipate needs and solve problems before they escalate
• Push tasks forward even when facing ambiguity, friction, or an initial “no”
• Research, escalate, and pursue alternative paths until the task is actually resolved
  
  

Support the CEO directly

• Assist with scheduling, coordination, research, logistics, and admin
  Deliver recommendations and conclusions, not raw information
• Handle sensitive topics with discretion and sound judgment
  
  

Use AI intentionally

• Use AI tools to accelerate research, analysis, and execution
• Maintain a human, thoughtful tone in all communications
• Never send obviously AI-generated content without refinement

💡 What We’re Looking For

Core traits (non-negotiable):

• Reliability: You consistently deliver, follow through, and catch details others miss
• Speed: You move fast, prioritize well, and don’t over-engineer simple requests
• Agency: You take ownership, find paths forward, and don’t stop at the first “no”

Experience & skills:

• Experience supporting a founder or senior executive in a fast-paced environment
• Strong personal systems for task tracking and prioritization
• Excellent written communication and judgment
• Comfortable working independently in an async, remote setup
• Strong intuition for when quality matters more than speed, and vice versa

🛠 Bonus (Very Nice to Have)

• Experience in startups or remote-first teams
• Familiarity with modern async tools (Notion, Slack, Google Workspace, task trackers)
• Experience using AI tools thoughtfully and effectively in daily work

✅ How We Hire: The Lean Hire Trial

Nearly all full-time roles at Cal.com begin with a 30-day contract-to-hire trial, which we call a Lean Hire.

This is a two-way evaluation:

• You get real exposure to the work, pace, and expectations
• We assess alignment, trust, and working rhythm without long-term risk

Success in a Lean Hire is about ownership, judgment, and momentum, not perfection.

✨ Why Work at Cal.com?

We’re building Cal.com not just as a product, but as a place to do great work and live a good life.

• 🌐 Work from anywhere, fully remote & async
  
• 💸 Location-agnostic compensation
  
• 📅 No standups, no micromanagement, no unnecessary calls
  
• 🪩 Real flexibility and autonomy
  
• 💻 Work in your own flow
  
• 🧘 30 paid OOO days per year
  
• ✈️ Yearly team retreats
  
• 👨‍👩‍👧‍👦 People-first, stable, kind culture