Executive Assistant to CEO (Part-Time)

SPIRIT; Chicago, Northern (IL, KY); Hybrid; USD 41,000 - 62,000; Part time

Job summary

SPIRIT is seeking a part-time Executive Assistant to support our CEO and co-founder, Alex. You will own the calendar, triage email, coordinate travel, and keep meetings running smoothly while protecting focus time.

This role offers 10–20 hours weekly, with HQ in Chicago and flexible location within the United States. You’ll work closely with our Chief of Staff and leadership team to keep operations efficient and moving.

Qualifications

• 2+ years supporting an executive, preferably at a tech startup.
• Fluent in Google Calendar and Gmail.
• Comfortable booking complex travel.

Responsibilities

• Own Alex's calendar day to day, scheduling and protecting focus time.
• Triage inbox and surface time-sensitive requests and travel needs.
• Maintain recurring meetings and leadership cadences, update invite lists.
• Book domestic and international travel and build detailed itineraries.
• Potential to flex into People Operations with the People team.

Skills

Calendar management

Email handling

Travel scheduling

Executive support

Tools

Google Calendar

Gmail

Job description

TL;DR: We're looking for a part-time Executive Assistant to Alex, our CEO and co-founder, to run the logistics around his calendar, inbox, and travel. This is a part-time role, ranging between 10-20 hours a week.

What You'll Do

• Own the calendar: You'll manage Alex's calendar day to day - scheduling, rescheduling, and blocking time so his week lines up with his priorities. You'll triage incoming meeting requests, protect focus time, and make sure nothing double-books or inadvertently gets dropped. You'll also keep an eye on the long-range calendar, making sure board meetings and other critical commitments are set well ahead and stay protected.
• Triage the inbox: You'll work through Alex's inbox - flagging what's time-sensitive, pulling out the scheduling and travel requests buried in it, and surfacing what needs a response first.
• Keep the recurring meetings running: You'll set up and maintain the recurring meetings Alex sits in - leadership cadences, company-wide sessions, and standing 1:1s - keeping invite lists current and moving things when the week shifts.
• Book travel and build the itinerary: You’ll manage all domestic and international travel for the CEO, building detailed itineraries that allow him to move between meetings, events, speaking engagements, recordings, and partner visits. You'll ensure every detail is accounted for before he leaves, from ground transport to a backup plan when a flight slips. As needed, you’ll also help support the travel needs of the executive leadership team.
• Possible Flex into People Operations: For someone who has full-time capacity, this role may have the potential to flex into supporting people operations, working with Hallow’s People team.

What You’ll Love

• Mission: This work is incredibly humbling. Every day we hear amazing stories and we get the pleasure of working on something that's impacting lives. One of our favorite user quotes: “I hate quoting an old, overused cliche, but I've been very lost. And I think for the first time in a while I may be found.”
• Ownership: You'll own how the CEO's time gets spent, which shapes what the whole company moves on. The calendar and the travel are yours to manage and maintain - you'll work directly with Alex and our Chief of Staff every week.
• Growth: From day 1, you'll be a part of the startup journey. You'll see how a fast-growing company runs from one of the closest seats to the CEO, working alongside our Chief of Staff and leadership team. In time, you may also pick up some light calendar and travel support for other members of our leadership team.
• Flexibility: HQ is in Chicago and we would love to have as many team members there as possible, but we are completely flexible on location within the United States.
• Comp: We will pay competitive market rates for this hourly, part-time position.

What We’re Looking For

• Passion: First and foremost, we're looking for someone excited and passionate about our mission. It makes it a lot more fun to actually care about what you're working on! :)
• Drive: You work quickly and are always willing to jump into new projects. You don’t mind pivots and love the scrappy, lean nature of startups. You adjust when day-to-day plans change, hold the line on what needs to stay locked, and you know how to get answers when people are moving fast.
• Problem solver: You enjoy working things out on your own, and you're a master at quick execution. You can stay on top of many moving pieces, and you use good judgment about what you can just handle and what should go to someone else.
• Follow-through: You keep things moving for the team - clearing blockers, chasing open threads, and closing the loop. You know what's outstanding at any given moment and what's coming months out, and you stay on top of details so nothing drops.
• Servant leader: You like making work easier for others, and no task is beneath you. You don't wait to be told what needs doing - you see what would help and you do it.
• Experience: 2+ years supporting an executive, preferably at a tech startup. You're fluent in Google Calendar and Gmail and comfortable booking complex travel.

Compensation Range

$30 to $45 USD per hour

This is a part-time, non-exempt hourly position and is not eligible for most employee benefits; paid sick leave is provided where required by state or local law. The above range is an initial estimate. Compensation may vary depending on market or location and may be adjusted depending on the person we end up hiring for this role, their experience, and market dynamics.