[Hiring] Executive Assistant to CEO @Proper

Role Description

The Executive Assistant / Personal Assistant (EA/PA) is a highly trusted partner responsible for providing comprehensive administrative, operational, and personal support to the CEO. This role serves as a central coordination point across multiple companies (Proper, Guardian, and Livly), acting as a key liaison between the executive, internal teams, and external stakeholders.

The EA/PA ensures that both organizational priorities and personal obligations are executed efficiently, with a high degree of discretion, professionalism, and sound judgment. This individual must be comfortable managing complex workflows, prioritizing competing demands, and operating independently in a fast-paced environment.

The ideal candidate is highly organized, detail-oriented, and proactive, with the ability to anticipate needs, streamline operations, and maintain confidentiality across both business and personal matters.

Qualifications

• Proven experience supporting C-level executives in an EA/PA or similar role.
• Strong background in calendar management, travel coordination, and executive support.
• Experience managing both professional and personal responsibilities for senior leadership.
• Familiarity with CRM systems, project management tools, and communication platforms.
• Ability to manage multiple priorities across different organizations simultaneously.
• Bachelor’s degree preferred.
• Experience supporting executives across multiple entities or business units.
• Familiarity with finance tracking, expense reconciliation, and operational systems.

Requirements

• Provide direct administrative and operational support to the CEO.
• Act as a liaison between the CEO and executive teams across Proper, Guardian, and Livly.
• Manage complex calendar scheduling, including business meetings, personal commitments, and travel.
• Coordinate corporate meetings, executive team sessions, and cross-company events.
• Prepare and manage weekly executive team recaps and communications.
• Exercise independent judgment in prioritizing tasks and resolving issues.
• Screen and manage email communications, responding on behalf of the CEO when appropriate.
• Handle sensitive and confidential information with discretion and integrity.
• Maintain contact databases and communication systems.
• Coordinate with internal stakeholders and external partners for scheduling and follow-ups.
• Manage domestic and international travel planning, including flights, accommodations, and itineraries.
• Track and manage travel credits, ensuring optimal utilization and cost efficiency.
• Maintain travel profiles, loyalty programs, and preferences.
• Coordinate conference registrations and travel-related logistics.
• Reconcile corporate and personal credit card expenses (Amex, Brex).
• Track receipts, invoices, and expense documentation for reporting and reimbursement.
• Manage corporate tools and platforms, including travel systems and communication tools.
• Support CRM management (Salesforce) and operational tracking where required.
• Manage personal appointments, calendars, and scheduling needs.
• Coordinate personal activities, including family events, weekend planning, and reservations.
• Oversee management of personal properties (e.g., Park City house scheduling and services).
• Coordinate gifting, flowers, and personal communications (e.g., birthday messages).
• Utilize and manage systems including Salesforce, Asana, Slack, Teams, SharePoint, and travel platforms.
• Maintain organized workflows for scheduling, communication, and expense tracking.
• Ensure adherence to company travel policies and operational procedures.
• Manage virtual communication tools and offshore support systems as needed.

Benefits

• Competitive compensation, commensurate with experience.
• Generous PTO and paid holidays.
• Opportunity to work closely with executive leadership across multiple growing companies.