Executive Assistant to the CEO

About the Opportunity

The organization is a leading employee leave management solution, simplifying the complex and often inefficient process for companies and their employees. It aims to transform leave management from a tedious, error-prone, and time-consuming task into a streamlined, 30-minute end-to-end experience, saving significant time and money per leave case. Headquartered in San Francisco, the company operates with a fully remote team across the country, fostering a diverse, talented, and supportive environment focused on solving real problems.

About the Role

The organization seeks an exceptional Executive Assistant/Personal Assistant to collaborate closely with the CEO during a pivotal growth phase. This role is designed to be a force multiplier, enhancing the CEO's effectiveness by optimizing her time for high-impact activities, accelerating decision-making, and ensuring strong follow-through on CEO-dependent tasks. The position is primarily focused on executive support (90%) with a smaller component of personal assistance (10%) to facilitate the CEO's overall productivity. While the role is fully remote, occasional travel (up to 25%) to the Bay Area may be required. Accountability, ownership, and flexibility in scheduling are paramount.

Key Responsibilities

• Collaborate with the CEO to align her schedule with top priorities and ensure her time is dedicated to high-impact work.
• Facilitate rapid decision-making and delegation to maintain organizational velocity.
• Develop action plans with the CEO for the completion of key initiatives and tasks.
• Proactively manage the CEO's inbox and complex calendar, ensuring meetings are purposeful and efficiently sequenced.
• Handle inbox management, including prioritizing, drafting communications in the CEO's voice, and managing event registrations or account setups.
• Ensure all written communications are clear, considerate, and tailored to the audience.
• Prepare necessary context and materials to maximize meeting efficiency and effectiveness.
• Track CEO-dependent projects, decisions, and action items across the executive team.
• Provide stakeholders with clear visibility into project status, dependencies, and next steps.
• Prevent project stagnation by ensuring timely follow-up and coordination.
• Demonstrate initiative in tackling tasks directly or proactively leveraging internal/external resources.
• Adopt a solutions-oriented approach to problem-solving.
• Develop and continuously refine systems and processes to enhance executive and organizational efficiency.
• Stay informed about tools and technologies that can improve administrative workflows.
• Propose improvements for smoother executive operations.
• Assist with personal calendar management, coordinating with professional commitments and avoiding conflicts.
• Schedule personal appointments while prioritizing professional responsibilities.
• Develop systems with the CEO to streamline personal logistics, such as meal planning or life administration.

Required Qualifications

• A minimum of 5 years of experience providing support to senior executives, preferably CEOs or founders in fast-paced, high-growth settings.
• Outstanding written communication abilities, including the capacity to adopt and replicate another person's writing style.
• Strong judgment and the ability to prioritize effectively, understanding the significance and rationale behind tasks.
• A proactive, high-ownership mindset with the ability to work autonomously.
• Proven experience in creating, enhancing, and maintaining operational processes.
• Professional demeanor and confidence when interacting with senior leaders and external parties.
• High emotional intelligence, discretion, and meticulous attention to detail.
• Comfort in managing both professional and limited personal logistical needs.

What This Role Is Not

• This is not a passive administrative role; success requires critical thinking, proactive ownership, and strategic judgment beyond mere task execution.
• This role is not confined by rigid boundaries; while primarily executive support, it includes personal assistance to maximize the CEO's overall effectiveness.
• This is not a gatekeeping position; the focus is on facilitating clarity, access, and momentum across the organization.
• This role is not suited for individuals who prefer highly structured, static environments; comfort with ambiguity and evolving priorities is essential.
• This is not a short-term stepping stone; it is designed for individuals seeking a long-term, trusted partnership with the CEO and the company.

Compensation and Benefits

This is a full-time salaried position with a compensation range of $80,000 to $140,000 annually, commensurate with experience. The role offers the opportunity to contribute to impactful work, supporting people teams and employees during critical life events. The company operates with the mission-driven focus of a nonprofit combined with the resources of a venture-backed startup. As an equal opportunity employer, the company values diversity and is committed to building an inclusive team with employees located across numerous states.