⚠︎ This job is no longer accepting applications.

Be the Candidate They Can't Ignore.

Don't just send a resume; set yourself up so the right work finds you.

  • Look like a pro instantly with a stunning personal brand.

  • Gain instant "Top Ten" status so you aren't just another name in a pile.

  • Wake up to booked meetings instead of "rejection" emails.

Join the Club — Free Forever
Job Closed

Executive / Personal Assistant to Lifestyle Content Creator

  • Source: Indeed
  • Red Soles and Red Wine
  • $41,600 to $62,400 /yr
  • On-site
  • Chicago
  • Mid level

Job Description

I’m a full-time content creator and entrepreneur in the fashion, beauty, home, and travel space looking for a highly organized, dependable Executive/Personal Assistant to help manage the day-to-day operations of my growing business.

This role is ideal for someone who genuinely enjoys creating order, building systems, and solving problems behind the scenes. If you love a well-managed calendar, an organized workspace, streamlined processes, and being the person who keeps everything running smoothly, you’ll thrive in this role.

While you’ll assist with content-related tasks, this is first and foremost an operations and executive support position. I’m looking for someone who takes pride in staying organized, anticipating needs, and making sure nothing falls through the cracks, with added bonus of some creative tasks.

Responsibilities

  • Manage calendars, appointments, deadlines, and project timelines
  • Keep the business organized by creating and maintaining systems for projects, inventory, digital files, and workflows
  • Receive, unpack, catalog, and organize incoming product shipments
  • Coordinate returns, exchanges, deliveries, and pickups
  • Anticipate needs, prioritize tasks, and proactively keep day-to-day operations running smoothly
  • Assist with administrative tasks, scheduling, and special projects
  • Run occasional business-related errands
  • Organize closets, product inventory, and content storage
  • Research fashion, beauty, home, lifestyle, and social media trends
  • Organize and manage content, photos, videos, and digital assets
  • Create affiliate links and product links across platforms
  • Assist with content planning, scheduling, and campaign organization
  • Create clean, elevated collages and graphics in Canva
  • Edit Instagram Reels, TikTok videos, and other short-form content as needed

Qualifications

  • Exceptionally organized with outstanding attention to detail
  • Naturally proactive—you notice what needs to be done before being asked
  • Strong follow-through and consistently completes tasks without reminders
  • Excellent written and verbal communication skills
  • Self-starter who takes ownership and solves problems independently
  • Loves creating systems, organizing spaces, and keeping projects on track
  • Professional, trustworthy, and comfortable handling confidential business and personal information
  • Calm, adaptable, and able to thrive in a fast-paced entrepreneurial environment
  • Strong project management and time management skills
  • Has an iPhone, personal laptop, valid driver’s license, and reliable transportation
  • Comfortable using Canva and basic video editing software (CapCut, Premiere Pro, Final Cut Pro, InShot, or similar) is a plus
  • Familiarity with Instagram, TikTok, affiliate linking, and content management platforms is helpful, but this is not a social media manager or content creator role
  • Previous experience as an Executive Assistant, Personal Assistant, Operations Coordinator, or Administrative Assistant is strongly preferred
  • Experience supporting an entrepreneur, small business, or content creator is a plus.

The ideal candidate gets genuine satisfaction from organizing, planning, and making someone else’s life easier. You love being the person behind the scenes who keeps everything running smoothly. This is part-time depending on performance but may become full time dependant on candidate.

Pay: $20.00 - $30.00 per hour

Work Location: In person

Skills

  • workspace
  • Canva
This job is no longer accepting applications.

You missed this one - but you don't have to keep missing out. Try Club members get matched with open opportunities before they're gone, so you're always first in line, never last.

Join the Club — Free Forever
Create Free Account & Apply
  • Free personal website
  • Built-in Talent Agent
  • Apply to future jobs in 1 click
  • Get matched to similar roles
or
Apply as a guest this time

You'll apply successfully, but won't be able to track your application, save this job, or get matched to similar roles.

This listing is a publicly available opportunity curated by Try Club to help talent discover relevant roles. Try Club is an independent platform and is not affiliated with Red Soles and Red Wine

Get Similar Jobs

Browse more similar roles on TRY and find your perfect match.

Show Me Similar Jobs

Stop Searching. Start Thriving.

Why waste time chasing leads when the perfect projects can find you?
With TRY, clients actively searching for professionals with your skills can discover you in seconds. Whether it's a quick gig or your dream role, we connect you with opportunities that matter.

  • Get found faster
  • Let projects come to you
  • Build a career on your terms

Take control of your career today.

Claim Free Website in 2 Minutes