Executive Assistant to the CEO

About Swooped

Our client, Swooped, offers a high-tech, high-touch employee leave management solution aimed at simplifying how organizations support employees through family, medical, and other types of leave. The company transforms complex, inefficient, and difficult-to-navigate leave processes into a streamlined, 30-minute end-to-end experience, saving teams significant time and money per case. Headquartered in San Francisco with a fully distributed team across the United States, Swooped is comprised of talented, collaborative, and mission-driven professionals dedicated to solving meaningful problems for People teams and employees.

About the Executive Assistant to the CEO Role

Swooped is seeking an exceptional Executive Assistant / Personal Assistant to partner closely with the CEO during a critical phase of growth. This position serves as a force multiplier for both the CEO and the broader organization, increasing the speed and clarity of decision-making, delegation, and execution. Approximately 90% of the role focuses on Executive Assistant responsibilities and 10% on Personal Assistant support. This is a fully remote position, potentially requiring up to 25% travel to the Bay Area. High accountability, ownership, and schedule flexibility are essential.

Key Responsibilities

• **Partner Closely with the CEO on Priorities and Execution:** Align the CEO’s time with highest-impact initiatives and enable faster delegation and decision-making. Support action planning for key strategic initiatives.
• **Own Inbox, Calendar, and Communications Management:** Manage a complex, fast-paced calendar with strong prioritization. Oversee inbox management, including tagging, drafting correspondence in the CEO’s voice, and independently handling administrative communications. Ensure written communication is thoughtful, clear, and audience-appropriate. Prepare context and materials for efficient meetings.
• **Drive Follow-Through and Executive Visibility:** Track CEO-dependent projects, action items, and decisions across the executive team. Provide stakeholders with visibility into status updates, dependencies, and next steps. Ensure timely coordination and prevent critical initiatives from stalling.
• **Operate with a High-Ownership Mindset:** Proactively take initiative on tasks when appropriate. Engage internal or external resources to ensure completion when needed. Approach challenges with a solutions-oriented and resourceful mindset.
• **Build and Improve Systems and Processes:** Develop and refine processes that increase executive and organizational efficiency. Stay current on tools and technology that improve workflows. Recommend improvements to strengthen executive operations.
• **Provide Light Personal Assistance:** Coordinate the CEO’s personal calendar alongside professional commitments. Schedule personal appointments while avoiding business conflicts. Help design systems that improve personal logistics efficiency (e.g., recurring administrative tasks, planning coordination).

Qualifications

• 5+ years of experience supporting senior executives, ideally CEOs or founders in high-growth environments.
• Exceptional written communication skills, including the ability to write in another individual’s voice.
• Strong prioritization skills and sound judgment.
• High ownership mindset with comfort operating independently.
• Experience building and maintaining effective processes.
• Professional presence and confidence interacting with senior leaders and external stakeholders.
• High emotional intelligence, discretion, and attention to detail.
• Comfort supporting both executive-level and limited personal logistics.

Compensation

This is a full-time salaried position with a compensation range of $80,000–$140,000, depending on experience and location.

Why Join Swooped?

Swooped offers a role with meaningful impact, supporting People teams and employees during pivotal life moments. The organization operates with a mission-driven mindset within a fast-growing, venture-backed company.

Key skills/competency

• Executive Support
• Calendar Management
• Inbox Management
• Communication Skills
• Prioritization
• Process Improvement
• Discretion
• Project Tracking
• High Ownership
• Stakeholder Management