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Remote Fun Jobs in Chicago, IL (NOW HIRING)

Process Street

Account Executive (Remote)

Chicago, IL · Remote

Our Mission To make work fun, fast, and faultless for teams everywhere. Our Culture Process Street was founded on a strong belief in the work-life benefits of a healthy, collaborative, remote culture.

Aoglobelife

Remote Sales Representative

Chicago, IL · Remote

Remote Sales Representative Company: AO Globe Life (a division of Globe Life) Location: 100% Remote (U.S. & Canada) Employment Type: Full-Time | Independent Contractor You've Got Sales Skills -- Let ...

Globe Life Insurance

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Remote Client Sales Representative (Entry-Level)

Naperville, IL · Remote

$60K - $80K/yr

Remote Client Sales Representative (Entry-Level) 100% Remote | United States & Canada | Full-Time | Training Provided | No Cold Calling | Weekly Pay Your Next Career Move Could Start From Home What ...

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Globe Life Insurance

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Remote Client Sales Representative (Entry-Level)

Chicago, IL · Remote

$60K - $80K/yr

Remote Client Sales Representative (Entry-Level) 100% Remote | United States & Canada | Full-Time | Training Provided | No Cold Calling | Weekly Pay Your Next Career Move Could Start From Home What ...

New

Globe Life Insurance

Be Seen First

Remote Client Sales Representative (Entry-Level)

Chicago, IL · Remote

$60K - $80K/yr

Remote Client Sales Representative (Entry-Level) 100% Remote | United States & Canada | Full-Time | Training Provided | No Cold Calling | Weekly Pay Your Next Career Move Could Start From Home What ...

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Showing results 1-20

All JobsFun JobsRemote Fun JobsRemote Fun Jobs in Chicago, IL

Remote Fun information

See Chicago, IL salary details

$21K

$71.9K

$167.8K

How much do remote fun jobs pay per year?

As of Aug 23, 2026, the average yearly pay for remote fun in Chicago, IL is $71,856.00, according to ZipRecruiter salary data. Most workers in this role earn between $39,517.00 and $92,377.00 per year, depending on experience, location, and employer.

What is a remote fun?

Remote Fun jobs are positions that allow individuals to work from any location while focusing on engaging, enjoyable, or creative tasks. These jobs typically emphasize a positive work-life balance and may include roles in gaming, entertainment, online event hosting, social media, or community management. The goal is to combine the flexibility of remote work with tasks that are stimulating and fun, often in dynamic and interactive environments.

What are the key skills and qualifications needed to thrive as a remote fun?

To thrive as a Remote Fundraiser, you need a solid understanding of fundraising principles, donor relations, and campaign management, often supported by a degree in communications or nonprofit management. Familiarity with donor management software such as Salesforce or Bloomerang, and experience with virtual communication tools, is highly valuable. Exceptional written and verbal communication, relationship-building, and self-motivation are the soft skills that set top performers apart. These skills ensure effective donor engagement, successful fundraising campaigns, and the ability to work independently in a remote environment.

What are some common challenges faced by employees working in remote fun coordinator roles, and how can they be addressed?

Remote fun coordinators often face the challenge of engaging a geographically dispersed team and fostering a sense of community virtually. Overcoming time zone differences and ensuring inclusivity in activities require careful planning and clear communication. Utilizing virtual collaboration tools and regularly seeking feedback from team members can help tailor events that resonate with everyone, maintaining high morale and participation.

What is the difference between Remote Fun vs Remote Customer Support?

AspectRemote FunRemote Customer Support
Required CredentialsTypically none; some roles may prefer basic tech or communication skillsOften requires customer service experience or certifications in communication
Work EnvironmentCasual, creative, flexible; often involves entertainment or engagement activitiesProfessional, structured; involves assisting customers via chat, email, or calls
Employer & Industry UsageUsed in entertainment, gaming, or social platformsCommon across retail, tech, and service industries
Search & Comparison IntentPeople looking for fun, engaging remote rolesPeople seeking customer service or support roles remotely

Remote Fun roles focus on entertainment and engagement, often with flexible credentials and a casual environment. In contrast, Remote Customer Support roles emphasize assisting customers professionally, often requiring communication skills and experience. Both are remote but serve different industry needs and work styles.

What are some fun remote jobs?

Fun remote jobs include roles such as social media manager, content creator, graphic designer, and virtual event planner. These positions often involve creative skills, digital tools, and flexible schedules, making them engaging options for those seeking enjoyable remote work.

What are the most commonly searched types of Fun jobs in Chicago, IL?

The most popular types of Fun jobs in Chicago, IL are:

What are popular job titles related to Remote Fun jobs in Chicago, IL?

For Remote Fun jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Fun jobs in Chicago, IL look for?

The top searched job categories for Remote Fun jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Fun jobs?

Cities near Chicago, IL with the most Remote Fun job openings:

Remote Fun jobs near you
Infographic showing various Remote Fun job openings in Chicago, IL as of August 2026, with employment types broken down into 90% Full Time, and 10% Part Time. Highlights an 100% Remote job distribution, with an average salary of $71,856 per year, or $34.5 per hour.

Senior Director of Sales

Together For Talent

Chicago, IL • On-site, Remote

$200K - $250K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 19 days ago

Job description

Sr Director of Sales | Enterprise SaaS
Location: Fully remote (in the US)
Salary: $200-250k + Commission (50/50)
WHO WE ARE
Headquartered in the US with teams across the globe, we are a leading enterprise software company focusing on SaaS solutions that help enterprises manage IT assets. Our platform optimizes software and cloud spend, improve compliance, and gain better visibility across hybrid IT environments with an emphasis on ITAM, SaaS management, and FinOps. Due to growth and demand for our product, we are urgently looking for a Senior Director of Sales to join our diverse and growing team!
This leader will manage 8 reps and help drive the company's transition from a regional sales structure to a vertical structure. The focus will be on healthcare and insurance customers, though prior vertical experience is a plus rather than a requirement.
WHO YOU ARE
  • A proven Sr Manager, Director, or emerging sales leader ready to step into a VP title while remaining deeply involved in deal strategy, coaching, and team performance.
  • Strong background in enterprise SaaS sales with 2-3 years of leadership or people management experience
  • Experience in ITAM, ITSM, or related enterprise technology categories
  • Exposure to FinOps and cloud cost management a strong plus
  • A track record of leading teams through complex, consultative sales motions
  • Strong in relationship-building across long sales cycles, typically 9-15 months
  • The ability to operate as a player-coach and support reps in strategic deals
WHAT WE OFFER
  • Competitive compensation: $200-250k DOE + 50/50 commission
  • Comprehensive benefits package (Medical, Dental, Vision)
  • Competitive PTO, including new-parent support
  • 401k
  • Student loan debt relief and tuition reimbursement
  • Fully remote
  • Fun, innovative, collaborative, and award-winning culture
So, if you're a sales leader ready for a career-defining opportunity, please apply today!