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Cool Remote Jobs in Chicago, IL (NOW HIRING)

Collectiv

Senior Power BI Consultant

Chicago, IL · On-site +1

At Collectiv, your career thrives with a perfect blend of remote flexibility, growth potential, and ... Keep Calm and Carry On - Stay cool, calm and Collectiv. Employment Type: FULL_TIME

VML

Freelance Program Director

Chicago, IL · On-site +1

Freelance Program Director (open to remote EST or CST) Who we are looking for: VML is seeking a ... cool under pressure. You are familiar with the complexities and regulations within marketing ...

Deckers

Account Executive, UGG - Chicago

Chicago, IL · On-site +1

Chicago, IL (Remote) The Role As an Account Executive for UGG, you'll manage all aspects of the ... From generous discounts to community-based programs, we offer a variety of cool extras * Growth and ...

Strike Social

Senior Data Scientist

Chicago, IL · Remote

We work in an agile environment with lots of cool toys. Our Data Scientists research and create our ... Working hours are flexible and remote work is encouraged. We are an equal opportunity employer and ...

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All JobsCool JobsCool Remote JobsCool Remote Jobs in Chicago, IL

Cool Remote information

See Chicago, IL salary details

$17

$22

$24

How much do cool remote jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for cool remote in Chicago, IL is $22.15, according to ZipRecruiter salary data. Most workers in this role earn between $18.56 and $23.51 per hour, depending on experience, location, and employer.

What is a cool remote?

A Cool Remote job is a position that allows professionals to work remotely while engaging in exciting, innovative, or unique tasks. These jobs often provide flexibility, work-life balance, and the opportunity to work from anywhere with an internet connection. They can span various industries, including tech, marketing, design, and customer service. Many Cool Remote jobs emphasize creativity, autonomy, and modern digital tools to enhance productivity.

What are the key skills and qualifications needed to thrive as a remote worker, and why are they important?

To thrive as a Remote Worker, you need strong self-management, time management, and digital literacy, often supported by previous remote work experience or relevant training. Familiarity with collaboration tools like Slack, Zoom, project management software, and cloud-based platforms is essential. Excellent communication, adaptability, and proactive problem-solving set top performers apart in this role. These skills enable consistent productivity, clear collaboration, and effective independence in a remote environment.

What are some common challenges faced when working in a remote role, and how can they be overcome?

Remote positions often present challenges such as maintaining effective communication, managing time zones, and preventing feelings of isolation. To address these, it's important to utilize collaboration tools, establish regular check-ins with your team, and set clear boundaries between work and personal life. Successful remote teams also encourage open communication and provide support systems to help employees stay connected and engaged.

What is the difference between Cool Remote vs Customer Support Specialist?

AspectCool RemoteCustomer Support Specialist
Required CredentialsHigh school diploma or equivalent; some roles may require technical skillsHigh school diploma or equivalent; customer service experience preferred
Work EnvironmentRemote, home-basedTypically remote or in-office customer service centers
Industry UsageCommon in tech, marketing, and creative fieldsWidely used across retail, telecom, and service industries
Search & Comparison IntentLooking for remote customer service roles with flexible optionsSeeking customer support roles, often in call centers or online

Cool Remote and Customer Support Specialist roles both involve assisting customers, but Cool Remote emphasizes remote work flexibility, while Customer Support Specialist can be in-office or remote. Both require communication skills, but Cool Remote may demand more technical knowledge depending on the industry.

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

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

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

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

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

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

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

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

Cool Remote jobs near you
Infographic showing various Cool Remote job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $46,072 per year, or $22.1 per hour.

Enterprise Account Executive - RethinkEd

Rethink

Chicago, IL • On-site, Remote

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 7 days ago

Job description

Are you an educator at heart yearning to make a greater impact? Do you love building relationships and helping others succeed? Are you an advocate for technology solutions that help all learners thrive?
About Us
At Rethink Ed, we believe learning should bring out the best in everyone. As the 2020 CODiE Award Winner for Best Social Learning Program for Students, 2021 Winner for Best Student Learning Capacity-Building Solution, and 2022 Cool Tool EdTech Finalist for Vizzle, we bring cutting-edge strategies to administrators, educators, students, parents, and caregivers to support effective, high-quality education of the whole child. Our evidence-based, technology-driven solutions are developed and delivered by leading experts in Social and Emotional Learning, Behavior Management and Special Education.
The Role
RethinkEd is seeking an Enterprise Account Executive to lead sales efforts with the nation's largest and most complex school districts. This role is designed for an experienced seller who understands how large urban districts operate, how they transact, and how decisions are made across multiple departments, funding sources, and stakeholder groups. The Enterprise Account Executive owns a small number of high-value districts and is responsible for managing multiple, concurrent opportunities within each account. Success in this role requires deep account planning, disciplined execution, and the ability to multithread relationships across executive, programmatic, and operational stakeholders.
Responsibilities:
  • Achieve or exceed a $1M+ annual quota through new and expanded opportunities within enterprise districts
  • Build and manage a robust, multi-opportunity pipeline within each assigned district
  • Expand RethinkEd's footprint across departments, programs, and initiatives in large and urban school systems
  • Establish trusted relationships with senior district leaders and functional owners across Special Education, MTSS, Student Services, Curriculum & Instruction, and related areas
  • Navigate complex procurement, contracting, and funding processes common to large districts
  • Partner closely with Customer Success, Services, Marketing, and Enablement to drive long-term district success, renewals, and expansion

Qualifications & Key Competencies
  • Deep understanding of large, urban school district structures and decision-making and Ability to manage long, complex sales cycles with multiple parallel opportunities
  • Strong account planning and opportunity orchestration skills
  • Comfortable qualifying, prioritizing, and sequencing deals within a single account
  • Skilled at aligning multiple stakeholder priorities to a cohesive district narrative and confident engaging senior leaders while maintaining momentum with stakeholders
  • Data-driven approach to managing sales, with experience using CRM systems and productivity tools.
  • 7+ years of sales experience, preferably in K-12 education, EdTech, or complex SaaS environments
  • Demonstrated success selling into large and urban school districts
  • Experience managing $1M+ quotas and enterprise-level accounts
  • Proven ability to manage multiple opportunities within a single large account
  • Strong understanding of district procurement, contracting, and funding structures
  • Bachelor's degree or equivalent professional experience

Why Join RethinkEd?
  • Mission-driven organization making a meaningful difference in the lives of students and educators.
  • Collaborative, growth-oriented culture that values innovation and accountability.
  • Competitive compensation package with performance-based incentives.
  • Comprehensive benefits, including health, dental, vision, retirement plan, and paid time off.
  • Remote-first workplace with flexibility and national reach.

Location: Remote opportunities are available to candidates who reside in the following states: AL, AZ, CT, FL, GA, HI, IA, IL, IN, KY, LA, MD, MA, MI, MN, MO, MT, NC, NE, NH, NJ, NV, OH, OR, PA, RI, TN, TX, VA, WA, WI, WY
Our commitment to an inclusive workplace
RethinkFirst is an equal opportunity employer and is committed to providing a workplace free from harassment and discrimination. We celebrate the unique differences of our employees because that is what drives curiosity, innovation, and the success of our business. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, pregnancy, genetic information, disability, status as a protected veteran, or any other protected category under applicable federal, state, and local laws. Accommodations are available for applicants with disabilities.
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