Executive Assistant to the Founder - I016

Industry

Recruitment / Staffing / B2B Services

Work Arrangement

Fully Remote

Job Type

Full-time

Work Schedule

40 hours per week. Monday to Friday 9 to 5pm EST.

About Pearl

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, make an impact, and build a long-term career. We believe in creating environments where your potential is recognized, your voice matters, and your success is tied to meaningful work—not short-term perks. Joining Pearl means stepping into opportunities that challenge you, support you, and set you up for lasting success.

Role Overview

This is not a traditional EA role. You will be the operating system behind Pearl’s founder and CEO — managing his time, inbox, relationships, and travel while simultaneously building AI-powered workflows that automate and scale the way he works. We are looking for someone who is equal parts sharp executor and curious builder.

The ideal candidate is operationally rigorous, comfortable giving a founder direct pushback when needed, and genuinely excited about implementing AI into real workflows — not just using ChatGPT to draft emails, but building agents, automating decision trees, and measuring the time saved. You will work cross-functionally with Pearl’s sales, marketing, recruitment, and account management teams, and you’ll be the connective tissue between the founder and everyone he works with.

Key Responsibilities

Calendar & Schedule Management

• Own founders calendar end-to-end: scheduling, rescheduling, conflict resolution, and protecting focus time
• Manage color-coded calendar system across meeting types 
• Prep and send a Start-of-Day (SOD) brief every morning with schedule, priorities, and context for each meeting
• Build pre-meeting briefs for investor and sales calls 

Inbox Management & Communications

• Triage founder’s inbox in real time using a label and classification system — knowing what to act on, what to draft, what to delegate, and what to surface urgently
• Draft investor follow-ups, warm intros, partnership comms, and internal handoffs
• Route inbound inquiries to the right team: sales leads to Sales, candidate referrals to Recruitment, partnership requests to BD

AI Implementation & Workflow Automation

• Identify tasks in the daily EA workflow that can be partially or fully automated using AI tools and agents
• Build and maintain AI-powered workflows: automated meeting note extraction, action item capture, follow-up scheduling, CRM updates
• Explore and implement AI agents for calendar management, inbox classification, research, and recurring operational tasks

Relationships, Travel & Cross-Functional Coordination

• Maintain and update founder's investor and VC database: contact records, meeting outcomes, follow-up cadences, relationship stages

• Manage all travel logistics: flights, hotels, ground transportation, itineraries, and day-of adjustments

• Coordinate event logistics: guest lists, outreach, RSVP tracking, day-of support, post-event follow-up

• Work cross-functionally with Pearl’s Growth, Sales, Matching, Recruitment, Account Management, and Finance teams

• Handle personal admin as needed (restaurant bookings, errands, subscriptions)
  
  

Must-Haves (Required)

• Experience in an executive assistant, operations, or chief-of-staff role supporting a founder or C-level executive
• Proven ability to manage a high-volume calendar, inbox, and travel across time zones with zero dropped balls
• Hands-on experience with AI tools in a work context — not just using ChatGPT casually, but actively applying AI to automate or accelerate real tasks (drafting, research, meeting notes, workflow automation)
• Strong English communication (written and verbal)
• Extreme ownership: you treat this role like it’s your company, not just your job
• Ability to work Eastern Time hours and respond to urgent requests outside standard hours when needed

Nice-to-Haves (Preferred)

• Experience building AI agents or automated workflows using tools like Zapier, Make.com, n8n, or custom GPTs
• Background working with startups, venture capital, or high-growth companies
• Familiarity with CRM tools (HubSpot), project management tools (Notion, Asana), and scheduling tools (Calendly)
• Prior experience managing investor relations, VC databases, or fundraising support

Success in This Role Looks Like

• The Founder’s day runs smoothly with no missed follow-ups or overlooked priorities.
• Meetings are well-prepared, with the Founder briefed in advance.
• The investor and partner database is consistently accurate and up-to-date.
• Introductions, outreach, and personal arrangements are handled seamlessly with minimal Founder intervention.

Benefits

• Fully remote
• Unlimited PTO
• Annual team retreat
• Direct exposure to US startup founders backed by a16z, OpenAI, and Founders Fund
• Work with a team that’s building the world’s best recruitment engine