Executive Assistant (High-Judgment Inbox & Calendar Operator) - A310

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 firmwe 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

Requirements

Must-Haves (Required)

• 3+ years of experience supporting a fast-moving founder or senior executive
• Prior experience using CRM systems in an executive support capacity
• Advanced executive calendar management experience in high-density environments
• High-volume inbox triage experience
• Excellent written English communication skills with executive-level drafting ability
• High reliability, punctuality, and organizational discipline
• Ability to thrive in fast-paced, high-expectation environments
• Strong working overlap with U.S. Eastern Time hours

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
• Claude (ability to build basic workflows and structured prompts)
• Slack
• Notion
• Stripe
• Brex
• 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

Benefits

• Competitive Salary: Based on experience and skills
• Remote Work: Fully remotework from anywhere
• Performance Bonus: Based on data accuracy, reporting timeliness, and overall sales efficiency
• Team Incentives: Recognition for maintaining 100% CRM hygiene and on-time reporting
• Generous PTO: In accordance with company policy
• Health Coverage for PH-based talents: HMO coverage after 3 months for full-time employees
• Direct Mentorship: Guidance from international industry experts
• Learning & Development: Ongoing access to resources for professional growth
• Global Networking: Connect with professionals worldwide

Our Recruitment Process

Application

Screening

Skills Assessment

Top-grading Interview

Client Interview

Job Offer

Client Onboarding

Ready to Join Us

If this role aligns with your skills and goals, apply now to take the next step in your journey with Pearl.