JobsExecutive AssistantChicagoExecutive Assistant to CEO (Part-Time)

Hallow

Posted 6 days ago

Executive Assistant to CEO (Part-Time)

Hallow · Chicago, Illinois, United States

Part-timeRemote2-5 yrsListed as no visa sponsorship
APPLY ON HALLOW'S CAREERS SITE ↗

Opens the employer's own application page.

In short

Manage the CEO’s calendar, inbox, recurring meetings, and domestic and international travel, ensuring priorities are protected and details are handled reliably. The role may also support executive leadership travel and, for someone with full-time capacity, assist the People team with people operations.

What they're looking for

MUST-HAVE SKILLS

Executive SupportCalendar ManagementInbox ManagementEmail TriageTravel BookingItinerary PlanningMeeting CoordinationGoogle Calendar

ALSO MENTIONED

Executive AssistantCEO SupportCalendar ManagementInbox TriageGoogle CalendarGmailTravel BookingDomestic TravelInternational TravelItinerary Planning

Applicants should have at least two years of experience supporting an executive, preferably at a technology startup, and be fluent in Google Calendar and Gmail. The role also calls for strong organization, judgment, initiative, adaptability, problem-solving, and a passion for the company’s mission.

About Hallow

Is your LinkedIn profile ready for roles like this?

A free review of your profile, scored against what Executive Support roles ask for, and what to fix first.

GET MY FREE REVIEWFREE · A SCORED REVIEW OF YOUR PROFILE, IN MINUTES

Questions about this role

Is this Hallow role remote?
Tagged remote.
Does it sponsor visas?
Listed as no visa sponsorship.
What experience does it ask for?
Listed as 2-5 years.

The posting, in full

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. 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.

▶ READ THE FULL POSTING
  • 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.

Similar roles open now

ALL 7 EXECUTIVE ASSISTANT ROLES IN CHICAGO

This listing comes from Hallow's own careers site. Apply links go to the employer. Last checked 5 Oct 2026.