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Executive Assistant (High-Judgment Inbox & Calendar Operator) - A310 at Pearl. Industry. Professional Services / Startup Operations. Work Arrangement. Fully Remote (Strong overlap required with U.S. Eastern Time working hours). Job Type. Full-time. Work Schedule. Monday to Friday — 40 hours per week. 9:00 AM – 5:00 PM EST (U.S. Eastern Time overlap required). Locations:. Open to candidates globally (must support U.S. Eastern Time hours). About Pearl Talent. Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund. They’re looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we’ve hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US.. Hear why we exist, what we believe in, and who we’re building for: . WATCH HERE. Why Work with Us?. At Pearl, we’re not just another recruiting firm—we connect you with exceptional opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, be challenged, and build long-term, meaningful careers.. About the Company. Our client is a fast-moving, high-performance startup operating in a high-volume, high-stakes environment. The executive team engages frequently with senior stakeholders, partners, and industry leaders, requiring precise coordination and structured communication systems.. The company values operational excellence, speed, sound judgment, and proactive problem-solving. This is an environment where context awareness, prioritization, and ownership are critical to success.. Role Overview. We are seeking a high-judgment Executive Assistant to take full ownership of inbox and calendar operations for a fast-moving executive. This role exists to remove the executive as the operational bottleneck by managing scheduling, triaging communications, and making context-aware prioritization decisions daily.. You will operate in a dense, high-volume environment where not all meetings or emails carry equal weight. Success in this role requires strategic calendar design, disciplined follow-up systems, and the ability to act independently without constant instruction.. This position is ideal for a proactive, highly organized operator who thrives under pressure, understands executive leverage, and executes with speed and precision.. Your Impact. In this role, you will directly improve executive leverage and organizational efficiency. Your work will:. Increase strategic focus by protecting executive time and enforcing priority tiers . Reduce operational friction through structured inbox and follow-up systems . Prevent scheduling and travel breakdowns before they occur . Ensure high-status stakeholders experience seamless coordination . Maintain operational stability in high-volume, fast-paced conditions . You will be instrumental in creating clarity, structure, and reliability within a demanding executive environment.. Core Responsibilities. Calendar Management & Scheduling – 40%. Own the executive’s calendar end-to-end across meetings, interviews, executive dinners, stakeholder calls, and strategic sessions . Design strategic time blocks aligned with stakeholder importance and executive priorities . Enforce structured buffer rules (e.g., 15-minute spacing every 1–2 hours) . Run confirmations, reschedules, and logistics checks proactively . Ensure calendar structure reflects prioritization and executive leverage . Inbox Triage & Follow-Up Systems – 35%. Triage high-volume inbox traffic and determine whether to respond, delegate, or escalate . Categorize emails by priority tiers (senior stakeholders, partners, internal teams, etc.) . Draft responses that accurately reflect the executive’s voice . Track open loops and proactively drive them to closure . Maintain structured follow-up systems to prevent dropped communication . Travel & Trip Logistics – 15%. Book travel and manage changes with precision . Coordinate trip logistics with ROI awareness and operational rigor . Prevent logistical breakdowns through proactive planning and verification . Operational & Gray-Area Support – 10%. Execute context-heavy tasks requiring independent judgment . Anticipate breakdowns before they occur . Operate effectively in ambiguous, fast-moving environments . Must-Haves (Required). 3+ years of experience supporting a fast-moving founder or senior executive . Advanced executive calendar management experience in high-density environments . High-volume inbox triage experience . Demonstrated ability to prioritize in high-stakes environments . Excellent written English communication skills with executive-level drafting ability . Strong contextual decision-making and independent judgment . High reliability, punctuality, and organizational discipline . Ability to thrive in fast-paced, high-expectation environments . Strong working overlap with U.S. Eastern Time hours . Prior experience using CRM systems in an executive support capacity. Nice-to-Haves (Preferred). Experience supporting high-growth startup executives . Experience interfacing with senior stakeholders (CMOs, CFOs, agency heads, industry leaders) . Exposure to operational or Chief of Staff-style responsibilities . Experience managing sensitive or confidential communications. Tools Proficiency. Must-Haves (Required). HubSpot . Slack . Notion . Stripe . Brex . Claude (ability to build basic workflows and structured prompts) . Google Workspace (Docs, Sheets, Calendar, Gmail). Nice-to-Haves (Preferred). Experience with AI workflow optimization . Familiarity with automation tools (e.g., Zapier) . Advanced calendar automation or scheduling tools. Company Location: Colombia.