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 idóneo 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
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
Competitive Salary: Based on experience and skills
Remote Work: Fully remote—work 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.

📌 Executive Assistant (High-Judgment Inbox & Calendar Operator) (Puerto Vallarta)
🏢 Pearl
📍 Puerto Vallarta