Executive Assistant

Job Overview

We are seeking a highly proactive and strategic Executive Assistant to serve as a trusted operational partner to an executive managing multiple high-impact business, community, and personal initiatives. Going beyond traditional administrative support, this part-time remote role functions as a true extension of leadership by building efficiency systems, managing complex project dashboards, and handling multi-channel communications. You will oversee a diverse spectrum of responsibilities ranging from project management and relationship tracking to family logistics, travel planning, and personal operations. The ideal candidate is a systems-thinker who seamlessly handles confidential data, anticipates bottlenecks, and leverages modern productivity and AI tools to maximize executive capacity.

Schedule

Mon-Fri, flexible during client business hours CST time (20 hours per week)

Responsibilities

Executive Operations & Planning

• Calendar Ownership: Manage a complex rolling calendar across business, board, professional, community, family, and personal commitments while proactively resolving conflicts.
• Prioritization: Maintain a macro view of upcoming commitments, deadlines, and strategic priorities; conduct weekly planning sessions and recommend tradeoff decisions.
• Friction Reduction: Identify operational loose ends, surface risks/bottlenecks before they arise, and ensure nothing falls through the cracks.
• Process Improvement: Recommend workflows and process enhancements that directly increase executive capacity and operational effectiveness.

Strategic Project Management

• Project Oversight: Maintain executive project plans, dashboards, timelines, and cross-functional operational reporting.
• Stakeholder Coordination: Drive accountability across internal and external stakeholders through regular follow-ups and executive check-ins.
• Systems Optimization: Develop repeatable workflows, templates, and standard operating procedures using systems thinking.

Communications & Relationship Management

• Executive Communications: Draft high-impact emails, presentations, reports, talking points, and meeting summaries.
• Inbox Management: Oversee inbox communications and follow-up correspondence to ensure timely, professional responses.
• Network Engagement: Maintain relationship management systems, tracking key engagements and coordination with investors, partners, clients, and community leaders.

Meeting & Event Management

• End-to-End Logistics: Coordinate executive meetings, retreats, conferences, board meetings, and networking events, including vendor and travel management.
• Meeting Execution: Prepare agendas, briefings, and presentation materials; capture outcomes, decisions, and action items to ensure momentum.

Research & Decision Support

• Strategic Intelligence: Research companies, industries, competitors, and software to prepare organized briefings that support executive decision-making.
• Professional Development: Source executive education, conferences, certifications, and leadership opportunities.

Executive Lifestyle & Personal Operations

• Family Logistics: Coordinate family travel, schedules, reservations, medical appointments, and special events.
• Educational & Career Support: Research college planning resources, application timelines, and support administrative aspects of career searches for designated family members.
• Wealth & Legal Administration: Coordinate meetings and documentation with financial advisors, tax professionals, attorneys, and specialized vendors.
• Discretion: Handle sensitive and confidential personal information with the highest level of integrity.

Administrative Operations

• Financial Administration: Process expense reports, reimbursements, and executive purchases.
• Data Management: Maintain organized digital filing systems, operational documentation, and accurate records.
• Workflow Approvals: Manage contracts, document signatures, subscriptions, and renewals.

Technology & Productivity

• PM Platforms: Optimize productivity and project platforms including ClickUp, Asana, Monday.com, Wrike, Notion, Airtable, Salesforce, HubSpot, Slack, M365, Google Workspace, and Zoom.
• AI & Automation: Leverage AI tools (ChatGPT, Copilot, Claude, Gemini) and emerging technologies to automate workflows, accelerate research, and improve communication efficiency.

Requirements

Required

• 2-5 years supporting senior executives, founders, CEOs, COOs, or executive leadership.

• Exceptional organizational, communication, and project management skills.

• Strong business judgment with the ability to anticipate needs and solve problems proactively.

• High level of professionalism, discretion, and confidentiality.

• Ability to manage multiple priorities independently in a fast-paced environment.

• Advanced proficiency with Microsoft Office and Google Workspace.

Preferred

• Experience supporting executives leading multiple businesses, initiatives, or organizations.

• Experience with ClickUp, Asana, Monday.com, Wrike, Slack, Microsoft Teams, Zoom, Salesforce, HubSpot, Notion, Airtable, and AI productivity tools.

• PMP, CAP, CSM, or comparable professional certifications.

• Experience building systems, operating rhythms, and executive workflows.

Independent Contractor Perks

Permanent work from home

Immediate hiring

Note

Please click the Apply button to complete your application, including the assessment questions, technical check, and voice recording. Your hourly pay rate will be established based on your performance in the application process; submissions with all requirements fulfilled will receive priority review.