Executive Assistant to the Founder

Summary

Join Pearl, a high-growth company connecting top talent with startups, as a highly organized and proactive Executive Assistant directly supporting the Founder & CEO. This critical role involves managing daily operations, maintaining investor and partner relationships, ensuring productive meetings, and maximizing the Founder's efficiency. You will act as the gatekeeper, anticipating needs, managing communications, and driving priorities forward. The ideal candidate possesses exceptional organizational and time-management skills, strong communication abilities, and a proactive, resourceful mindset. This is a remote, full-time position offering unlimited PTO, health benefits, and significant bonus opportunities.

Requirements

• 3+ years in an Executive Assistant, Chief of Staff, or operations coordination role (startup or founder support experience preferred)
• Exceptional organizational and time-management abilities
• Strong written and verbal communication skills
• High attention to detail and accuracy
• Ability to manage multiple priorities in a fast-paced environment
• Proactive and resourceful, anticipating needs before they arise
• Comfortable with high levels of responsibility and confidentiality
• Values-driven and deeply aligned with Pearl’s core principles
• Thrives in a fast-moving, high-expectation environment where priorities can shift quickly
• Energized by working closely with a highly driven, detail-focused leader

Responsibilities

• Prepare and send Start-of-Day (SOD) emails summarizing the Founder’s schedule, priorities, and meeting details
• Flag scheduling conflicts and coordinate calendar adjustments
• Block heads-down work and personal time in the Founder’s calendar
• Monitor and triage the Founder’s inbox throughout the day
• Draft responses, delegate messages, and ensure urgent matters are addressed promptly
• Maintain concise, accurate, and professional communication on behalf of the Founder
• Maintain and update detailed contact records
• Capture new leads, investors, and partners
• Log follow-ups, next steps, and meeting outcomes to ensure no opportunities are missed
• Set and track follow-up dates for key contacts
• Send reminders, bump emails, and coordinate with the Founder on high-touch outreach
• Support investor and partner engagement through warm introductions and curated communication
• Schedule and confirm meetings with accurate time zone management
• Provide the Founder with pre-meeting briefs, including attendee bios, context, and objectives
• Prepare documents for internal candidate interviews
• Maintain the VC & investor database
• Share updated lists with founders/contacts upon request
• Coordinate introduction requests and follow up with VCs and investors
• Conduct EOD sync with the Founder to recap the day’s meetings, outcomes, and next steps
• Update contact records, priorities, and schedules based on new developments
• Prepare the following day’s meeting briefs and schedule adjustments
• Assist with compiling guest lists and outreach for Founder-led events
• Coordinate pre- and post-event communications
• Accomplish ad hoc tasks for the Founder, including: Booking flights, arranging travel, and securing accommodations Handling personal and business finances as directed Making dinner reservations and coordinating restaurant bookings Running personal errands Handling time-sensitive research, document preparation, and other special projects

Benefits

• Fully WFH
• Unlimited PTO
• Health Benefits
• Significant Quarterly Bonus and Yearly Performance Bonus
• Annual team retreat