Gig
$5
10
Jul 10, 2026
Read the entire post and information about how to apply. Important: This role requires outstanding fluency in spoken and written English.
ABOUT US AND THE ROLE
Ice Cream Sunshine is a good vibes signature ice cream tour and special events company based in Chicago. Good vibes, excellence, and fun are the core of who we are — and that extends to every person on our team.
We are looking for a project-based Executive Assistant to join us long-term as part of our on-call team of specialists. If you bring 3+ years of experience supporting executives or in a similar role, thrive without hand-holding, and love figuring things out and delivering ahead of schedule — let's connect.
This is on-call, project-based work — assignments typically run 2+ hours and often longer. We're building a bench of EAs who each bring a different edge: some sharper in social media, some in logistics, some in operations, some in finance. Tell us where you shine.
WHAT YOU WILL DO
You'll work directly with the founder and operations team across a variety of assignments that keep the business moving.
- Manage communications —
- Own assigned projects from kickoff to completion — track timelines, flag risks early, and deliver without being chased
- Build and manage forms, organize data, and conduct research across vendors, tools, and pricing — delivered as clean, concise summaries, not data dumps
- Draft
- Spot repeated tasks and build systems or SOPs around them
- Support day-to-day operations, including vendor coordination and project logistics
GOOD VIBES ONLY COMPANY
We believe in good vibes, respect, value, appreciation, and fun as a company culture. We perform with excellence and have a good time along the way.
WHAT WE ARE LOOKING FOR
We're looking for someone self-directed, detail-obsessed, and genuinely energized by solving problems with little to no guidance.
- 3+ years supporting executives or in a similar role
- 1+ years of project management experience
- 3+ years working with US-based employers
- Skilled with CRM tools, Google Workspace, Microsoft 365, and a broad tech stack — and excited to pick up new tools
- Outstanding at building forms and working with data
- Deadline-driven — early is on time here
- Discreet — you handle sensitive information with care at all times
- Your own computer with reliable, secure, high-speed internet
You go to the top of our list if you: don't wait for direction — you create it, bring ideas, and move things forward on your own.
WHAT SUCCESS LOOKS LIKE
We measure results.
- Projects delivered early, not just on time, with minimal need for follow-up
- Clean, concise summaries instead of raw data dumps
- Communications that sound like the founder — no rewrites needed
- Repeated tasks turned into simple systems or SOPs
- A track record that earns more projects and eventually part-time hours
WHAT WE OFFER
- $5hr USD starting compensation
- On-call, project-based work — assignments typically 2+ hours, often longer
- A real path to part-time and full-time as we grow
- A direct, collaborative relationship with the founder and operations team — your expertise is valued
- A supportive, respectful company culture where people genuinely enjoy working together
- Fun virtual team events
- We treat you to lunch and sweets ????
- Birthday celebrations? Yes. We celebrate you.
HOW TO APPLY
Write us a cover letter in your own words — no AI. Tell us:
1 — Why are you applying, and what about your background most aligns with this role?
2 — What's one example of a challenging assignment beyond your core job responsibilities — what was it, what did you do, and what was the outcome?
3 — What is your specialty edge — social media, logistics, operations, finance, or something else — and how has it shown up in past work?
4 — What has brought you the most fulfillment in previous roles?
5 — What makes a great remote working relationship, and how do you personally show up to make it work? Include how long you've been a full-time remote worker.
6 — Share your portfolio and CV links.
Bonus (optional)
1 — What is your favorite ice cream flavor? Share a pic.
2 — Share a link to a short 1–2 minute video on why you have joy in being an EA and what you love about ice cream.