Executive Assistant to CEO (Part-Time)

Hallow•Chicago, IL

4d•$30 - $45•Remote

About The Position

We are seeking a part-time Executive Assistant to support our CEO and co-founder, Alex. This role focuses on managing his calendar, inbox, and travel logistics. The position requires 10-20 hours per week. The ideal candidate will be passionate about our mission, possess a strong drive, be an excellent problem-solver, demonstrate great follow-through, and embody a servant leader mentality. Experience supporting an executive, preferably in a tech startup, is required, along with fluency in Google Calendar and Gmail, and comfort with booking complex travel.

Requirements

2+ years supporting an executive, preferably at a tech startup.
Fluent in Google Calendar and Gmail.
Comfortable booking complex travel.
Passion for the company's mission.
Works quickly and willing to jump into new projects.
Adaptable to pivots and comfortable with the scrappy nature of startups.
Ability to adjust to changing daily plans while holding the line on essential tasks.
Skilled at finding answers quickly.
Enjoys working things out independently and executing quickly.
Ability to manage multiple moving pieces.
Good judgment in determining what to handle independently versus escalating.
Keeps things moving for the team by clearing blockers and chasing open threads.
Knows what is outstanding and what is coming up.
Stays on top of details to prevent anything from dropping.
Likes making work easier for others; no task is beneath them.
Proactively identifies and addresses needs without being told.

Nice To Haves

Potential to flex into supporting people operations for individuals with full-time capacity.
Support for other members of the leadership team's calendar and travel in the future.

Responsibilities

Manage the CEO's calendar, including scheduling, rescheduling, and blocking time to align with priorities.
Triage incoming meeting requests, protect focus time, and prevent double-bookings.
Monitor the long-range calendar for critical commitments like board meetings.
Process the CEO's inbox, flagging time-sensitive items, scheduling, and travel requests.
Set up and maintain recurring meetings, ensuring current invite lists and adjusting as needed.
Book all domestic and international travel for the CEO, creating detailed itineraries.
Account for all travel details, including ground transport and backup plans for flight delays.
Support the travel needs of the executive leadership team as needed.
Potentially flex into supporting people operations for individuals with full-time capacity.