Executive & Operations Assistant

About the Organization

This is a fast-scaling private membership community for entrepreneurs, founders, investors, and senior business leaders who are navigating life after major company exits. The organization curates high-end events, meaningful introductions, and shared experiences that strengthen a network built around innovation, collaboration, and lasting influence.

About the Role

The team is looking for a highly organized, detail-focused, and proactive Executive & Operations Assistant to help manage executive priorities, day-to-day operations, and the overall member experience.

This position is more than traditional calendar support. You will act as an operational partner, coordinating communication, supporting projects, assisting with exclusive events, improving internal systems, and keeping backend operations running smoothly.

This is a remote position based in Costa Rica, and it is offered on a full-time independent contractor basis.

Applicants must submit their CV in English. Advanced English at a C1 level or higher is required.

Key Responsibilities

• Oversee executive schedules, meeting planning, and calendar coordination.
• Manage a high volume of communication through email, Slack, and related collaboration tools.
• Arrange meetings with founders, investors, partners, and community members.
• Support the planning and delivery of private events, including vendor coordination, logistics, speaker management, and attendee communication.
• Maintain professional, timely relationships with internal and external stakeholders.
• Capture and document workflows, operating procedures, and internal guides.
• Keep tools such as Notion, CRM systems, and internal databases structured and up to date.
• Identify ways to streamline operations through process improvement and automation.
• Coordinate projects, track follow-ups, and help drive execution across multiple initiatives.
• Contribute to building repeatable systems that improve member service and internal efficiency.
• Use AI tools and automation platforms to increase productivity where appropriate.

Requirements

• At least 3 years of experience in an Executive Assistant, Operations Coordinator, Project Coordinator, or comparable role.
• Strong written and spoken English communication skills at an advanced level.
• Excellent organization, accuracy, and attention to detail.
• Proven ability to juggle multiple priorities and coordinate projects effectively.
• Comfort working with limited supervision while managing competing tasks.
• Polished communication style and confidence when engaging with senior leaders.
• Strong ownership mindset with a solution-oriented approach.
• Ability to handle confidential information with discretion.
• Readiness to work in a fast-moving, changing environment.

Preferred Experience

• Background supporting founders, executives, or startup leadership teams.
• Hands-on experience with Notion, Airtable, CRM tools, or project management software.
• Familiarity with workflow automation tools such as Zapier, Make, or similar platforms.
• Exposure to AI tools, AI assistants, or productivity automation workflows.
• Experience in event coordination or community operations.
• Prior work in startups, venture capital, entrepreneurship, or other high-growth settings.

What Success Looks Like

• Executive priorities are handled smoothly with little oversight.
• Internal operations become better organized and easier to scale.
• Events are delivered seamlessly with strong attention to detail.
• Members, partners, and stakeholders enjoy an excellent experience.
• Systems and automation continuously improve operational performance.

Why This Role Stands Out

• Work closely with successful entrepreneurs, investors, and business leaders.
• Gain exposure to a high-level entrepreneurial network.
• Contribute meaningfully to a fast-growing organization.
• Enjoy remote-first flexibility with occasional involvement in exclusive events.
• Be part of a collaborative, innovative, and high-performance team.

Compensation

The monthly compensation for this role is USD 1,500 to USD 2,000.

Additional Information

This role is a remote/telecommute opportunity.

Employment type: Full-Time | Independent Contractor.