Best Executive Assistant Hired This Week | Excellence in Project Management & Tech Tools | Project-Based to Part-Time

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: TYPE OF WORK

Any

: WAGE / SALARY

$5 - $7usd

: HOURS PER WEEK

TBD

: DATE UPDATED

Jun 15, 2026

JOB OVERVIEW

READ THE ENTIRE POST — specific steps are required to apply.

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ABOUT US

Ice Cream Sunshine is a signature ice cream tour and special events company in Chicago. People who join our tours have loads of fun while we explore Chicago neighborhoods, enjoy delicious ice cream treats at featured local businesses, and learn fun facts about ice cream and the city. Guests smile, mingle, laugh, and enjoy America's #1 dessert. Good vibes…it is the core of who we are.

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THE OPPORTUNITY

We are looking for a sharp, self-directed executive assistant who is ready to hit the ground running on projects, and grow with us over time. This role starts project-based with a real path to part-time and eventually full-time as Ice Cream Sunshine scales.

You will work directly with the founder and operations manager on a variety of assignments that keep the business moving forward. No hand-holding. No waiting for direction. You figure things out, deliver on time (early, actually), and bring your best every time.

You are available between 9:00 AM and 12:00 PM CDT for meetings and collaboration. Beyond that window, you manage your own schedule to meet deadlines.

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WHAT YOU WILL DO

Founder Support
Manage communications — emails, messages, and follow-ups — with professionalism and care. Protect the founder's time by owning tasks and flagging only what truly needs owner input. Handle all business information with strict confidentiality.

Business Support

As a growing startup, Ice Cream Sunshine moves fast and needs a tea ---------- mber who is nimble, resourceful, and thorough. You bring ideas, complete tasks with care, and assist with both professional and personal needs that allow the founder to focus on what matters most.

Project Management
Own assigned projects from kickoff to completion. Track timelines, flag risks early, and deliver results without being chased. Early is on time here.

Forms, Data & Research
Build and manage forms, organize and work with data, and conduct research across vendors, tools, pricing, and more. Deliver clean, concise summaries — not data dumps.

Written Communication
Draft emails, follow-ups, and messages that sound like the founder. Clear, professional, and on brand every time.

Process & Systems
Spot a repeated task and build a system around it. Contribute to SOPs and operational efficiency as the business grows.

Operations Support
Assist with vendor coordination, project timelines, and day-to-day business activities that keep Ice Cream Sunshine running smoothly.

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WHAT WE ARE LOOKING FOR

Requirements
- 1+ years of project management experience
- 3+ years supporting executives or in a similar role
- 3+ years working with US-based employers
- Expert in CRM tools, Google Workspace, Microsoft 365, and a broad tech stack — and genuinely excited to adopt new tools
- Outstanding at building and managing forms and working with data
- Exceptional written and spoken English
- Attention to detail — you catch errors before they become problems
- Deadline-driven — early is always on time
- Self-directed — you do not wait to be told, you figure it out and deliver
- Discreet — you handle sensitive information with care and confidentiality at all times
- Collaborative — you work well with people and bring a positive, professional presence to every interaction
- Your own computer with reliable, extremely secure high-speed internet

You Go to the Top of Our List If You:
- Do not wait for direction — you create it. You bring ideas, take initiative, and move things forward
- Have an outstanding understanding of people and technology, and genuinely enjoy finding new tools and solutions

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WHAT WE OFFER

- $5–$7/hr USD + bonus plan
- Project-based start with a real path to part-time and full-time as we grow
- A direct, collaborative relationship with the founder and operations manager — your perspective is valued
- A supportive, respectful team 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

A cover letter is required. Begin your cover letter with your first available start date and your availability this week for an interview between 9:00 AM and 12:00 PM CDT.

Note: When sharing your availability, list it in the Chicago time zone, CDT.

Part One
After reading the details of the role — why are you applying, and what about your background most aligns with this position?

Part Two
- What has brought you the most fulfillment or joy in previous roles?
- Share one example of a challenging assignment beyond your core job responsibilities — what was it, what did you do, and what was the outcome?
- What type of work do you aspire to that you have not yet done?

Part Three
What makes a great remote working relationship — and how do you personally show up to make it work? Include how long you have been a full-time remote worker and one or two lessons learned along the way.

Bonus
- Share two or three of your social media links — or if you do not have any, share a link to a 1–2 minute video of you talking about your favorite ice cream
- Post two or three favorite accounts you follow on socials
- For something fun, attach a picture of ice cream ????

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In this role you may be asked to take on tasks that fall outside of your initial scope for the success of the business. As the business grows, additional tea ---------- mbers will be hired and those assignments will shift accordingly.

Essential qualities: you love to learn and you love to have fun :+)

The team at Ice Cream Sunshine wishes you joy always. :+)

SKILL REQUIREMENT

Administrative Support Executive Assistance Virtual Assistant

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Best Executive Assistant Hired This Week | Excellence in Project Management & Tech Tools | Project-Based to Part-Time

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

WAGE / SALARY

HOURS PER WEEK

DATE UPDATED

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