Remote Chief of Staff & Executive Assistant

Pearl

2d • Remote

About The Position

An early-stage, founder-led company in the healthcare and consumer space is building data-driven outreach and operations, looking for a Chief of Staff & Executive Assistant to protect founder focus time and own both executive support and research operations end-to-end. The business is run by two founders in a lean, fast-moving remote setup where a single trusted hire moves fluidly between high-trust administrative work and hands-on market research — no layers of process, just direct ownership. Day-to-day, the role manages both founders' inboxes and calendars, coordinates meetings and travel, tracks expenses and vendor invoices, and maintains shared documentation, while dedicating roughly half the week to building research spreadsheets, sourcing verified contact data, and queuing outreach. Success means founders stay focused on high-leverage work while a reliable system handles scheduling, logistics, and a steadily growing, well-organized research pipeline.

Requirements

• 3+ years of executive assistant or executive support experience for founders or C-level leaders in a remote environment.
• Hands-on management of executive inboxes and calendars across multiple stakeholders and time zones, including scheduling and conflict resolution.
• Strong proficiency in Google Workspace (Google Sheets, Gmail, Google Drive, Google Calendar).
• Demonstrated experience building and maintaining research or contact databases at scale (e.g., verified contact directories, structured data sets).
• Experience coordinating travel, expense tracking, reimbursements, and vendor/invoice processing.
• Working use of AI tools (Claude or ChatGPT) for day-to-day research and drafting tasks.
• C1+ English (CEFR) for founder- and client-facing written and verbal communication.

Nice To Haves

• Prior experience supporting founders or C-level leaders at an early-stage or fast-paced startup.
• Background in healthcare, consumer, or B2C environments.
• Familiarity with lightweight CRM tools or Google Sheets–based outreach workflows.
• Experience queuing or managing outbound and lead-generation workflows.
• Light project management across multiple operational workstreams.

Responsibilities

• Manage founders' inboxes and calendars.
• Coordinate meetings and travel.
• Track expenses and vendor invoices.
• Maintain shared documentation.
• Build research spreadsheets.
• Source verified contact data.
• Queue outreach.

Benefits

• Competitive Salary: Based on experience and skills
• Remote Work: Fully remote—work from anywhere
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed