Executive Assistant to the CEO

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About the Opportunity

The organization is the first high-tech, high-touch employee leave management solution. Its mission is to make it simple for companies to provide their employees with all kinds of leave (i.e. family, medical, etc.).

Currently, the leave management process is painful and inefficient for everyone. Company leaders struggle to keep up with regulations and processes that change frequently, and the employees going on leave are overwhelmed by bureaucracy at an exceptionally important juncture in their career. The solution transforms this ordinarily tedious, error-prone, complex to remain compliant, and time-consuming process into a 30-minute end-to-end experience saving teams time (20 - 40 hours per leave) and money (up to $30K per leave).

The organization is headquartered in San Francisco but all employees work remotely across the country. The team is diverse, highly talented, and supportive. Together, team members are hardworking, collaborative, smart, and humble—after all, they’re solving real problems.

About the Role

The organization is looking for an exceptional Executive Assistant / Personal Assistant to partner closely with the CEO during a critical phase of growth.

The CEO views her role as setting the organization’s vision and hiring and managing a high-performing executive team. Her time is extremely limited—and it’s essential that she spends that time only on the highest-impact work that requires her attention.

In this role, the individual will act as a force multiplier for the CEO and for the organization as a whole. This role will help increase the velocity at which the CEO can meet, delegate, and make decisions, while ensuring strong follow-through and visibility across the executive team on CEO-dependent work.

This role is expected to be 90% Executive Assistant work and 10% Personal Assistant work, supporting both professional and limited personal logistics so the CEO can operate at her highest level. This is a fully remote role but may require up to 25% travel to the Bay Area, where the CEO is located. This is a role where accountability and ownership are extremely important, and at times it may require the schedule to flex with little notice.

Key Responsibilities

Partner closely with the CEO on priorities and execution

• Work with the CEO to understand her highest-impact priorities and ensure her time is aligned accordingly
• Help keep the organization moving at high velocity by enabling faster decision-making and delegation
• Partner with the CEO to action-plan how key initiatives and tasks will be completed

Own inbox, calendar, and communication management

• Manage a complex and fast-moving calendar, ensuring meetings are purposeful, prioritized, and sequenced effectively
• Own inbox management, including tagging, drafting emails in the CEO’s voice, and independently handling communications such as event registrations or account setup
• Ensure written communication is clear, thoughtful, and tailored to the reader’s perspective
• Prepare context and materials so meetings are efficient and effective

Drive follow-through and executive visibility

• Track CEO-dependent projects, decisions, and action items across the executive team
• Provide visibility to relevant stakeholders on status, dependencies, and next steps
• Ensure nothing important stalls due to lack of follow-up or coordination

Operate with a high-ownership mindset

• Take initiative to directly tackle tasks when appropriate
• When not the right person for a task, proactively leverage internal partners or external resources to get it done
• Approach problems with a solutions-oriented, “figure it out” mentality

Build and improve systems and processes

• Create and continuously improve processes that increase executive and organizational efficiency
• Stay up to date on tools and technology that improve administrative workflows
• Bring recommendations for how the organization’s executive operations can run more smoothly

Provide light personal assistance

• Maintain the CEO’s personal calendar and ensure it is coordinated with work commitments
• Schedule personal appointments while avoiding conflicts with professional priorities
• Partner with the CEO to build systems that make her personal life more efficient (e.g., meal planning, wardrobe management, recurring life admin)

Required 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 clearly in another person’s voice
• Strong judgment and prioritization instincts. The individual knows what matters most and why.
• A high-ownership mindset and comfort operating independently
• Experience creating, improving, and maintaining processes
• Professionalism and confidence working with senior leaders and external stakeholders
• High emotional intelligence, discretion, and attention to detail
• Comfort supporting both professional and limited personal logistics

What This Role Is Not

• This is not a passive, task-only administrative role. Success requires strong judgment, proactive ownership, and the ability to think critically about priorities—not just execute instructions.

• This is not a role with rigid boundaries between responsibilities. While the role is primarily Executive Assistant work, it includes Personal Assistant support. The goal is to enable the CEO to operate at her highest level—not to adhere to an inflexible job description.

• This is not a gatekeeping or power-centered role. The Executive Assistant is a facilitator and partner, not a blocker. The goal is to increase clarity, access, and momentum across the organization.

• This is not a role for someone who prefers highly structured, static environments. Priorities will evolve, and success requires comfort with ambiguity and change.

• This is not a stepping-stone role for someone uninterested in long-term partnership. This role is designed for someone who wants to build a trusted, enduring partnership with the CEO and grow alongside the organization.

Compensation

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

Why This Opportunity?

The work is impactful. The organization helps People teams with one of the hardest parts of their job, and it supports employees at a time when they need it most. The team is driven by its mission, much like a nonprofit, but with the resources and scale of a fast-growing venture-backed company.

The organization is proud to be an equal opportunity employer. While united by excitement for the mission and product, the diversity of experiences is one of the organization's strengths. The team is made up of people with all types of backgrounds, and there are teammates in 40 states and counting.

The hiring company is an equal opportunity employer committed to building a diverse and inclusive team.