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Remote Anytime Jobs in Chicago, IL (NOW HIRING)

Versa Networks

MSP Account Executive - Chicago

Chicago, IL · On-site +1

$200K - $280K/yr

Our mission is to secure anywhere, anytime access to anything. As a leader in Secure SD-WAN, SSE ... Enjoy the flexibility of remote work, and hybrid option to create the work schedule that works best ...

Versa Networks

MSP Account Executive - Chicago

Chicago, IL · Remote

$200K - $280K/yr

Our mission is to secure anywhere, anytime access to anything. As a leader in Secure SD-WAN, SSE ... Enjoy the flexibility of remote work, and hybrid option to create the work schedule that works best ...

DuPage County Health Department

Accountant

Wheaton, IL · On-site +1

$51K - $69K/yr

County Farm Road- Wheaton, IL Job Type: Full Time (37.5 hours per week) Remote Employment: Flexible ... You may speak to a doctor anytime through the Teledoc program, which provides access to U.S. board ...

All JobsAnytime JobsRemote Anytime JobsRemote Anytime Jobs in Chicago, IL

Remote Anytime information

See Chicago, IL salary details

$86K

$130.9K

$176.2K

How much do remote anytime jobs pay per year?

As of Aug 6, 2026, the average yearly pay for remote anytime in Chicago, IL is $130,860.00, according to ZipRecruiter salary data. Most workers in this role earn between $112,300.00 and $147,800.00 per year, depending on experience, location, and employer.

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

To thrive as a Remote Customer Service Representative, you need strong communication skills, problem-solving abilities, and typically a high school diploma or equivalent. Familiarity with customer relationship management (CRM) software, live chat systems, and ticketing platforms is often required. Outstanding time management, self-motivation, and active listening set top performers apart in this role. These skills ensure effective customer interactions, efficient issue resolution, and productivity in a remote work environment.

What does a remote anytime job mean?

A 'Remote Anytime' job refers to a position that allows employees to work remotely from any location and with flexible hours. This means you can choose when and where you work, offering greater autonomy over your schedule. These roles are ideal for individuals who need to balance work with other commitments or prefer a non-traditional work structure. However, expectations for communication and project deadlines still apply, so time management and self-discipline are important.

What are some common challenges faced by employees working in a remote anytime role, and how can they be addressed?

Employees in a Remote Anytime role often enjoy flexible work hours and the ability to manage their own schedules, but they may also face challenges such as staying motivated without direct supervision, managing work-life boundaries, and maintaining clear communication with team members across different time zones. To address these challenges, it is helpful to establish a consistent routine, set clear expectations with your manager, and use digital collaboration tools to stay connected. Regular check-ins and proactive communication can also help ensure alignment with team goals and foster a sense of connection despite physical distance.

What is the difference between Remote Anytime vs Customer Service Representative?

AspectRemote AnytimeCustomer Service Representative
Required CredentialsHigh school diploma or equivalent, basic tech skillsHigh school diploma or equivalent, communication skills
Work EnvironmentRemote, flexible hoursRemote or in-office, standard shifts
Industry UsageCustomer support, tech support, salesCustomer support, retail, telecom
Common Search IntentFlexible remote jobs, part-time remote rolesCustomer service jobs, remote support roles

Remote Anytime offers flexible, remote work options often suited for various industries, while Customer Service Representative roles focus on customer support tasks, typically requiring strong communication skills. Both roles are popular in remote work searches, but Remote Anytime emphasizes flexibility, whereas Customer Service Representative positions are more specialized in customer support functions.

What are popular job titles related to Remote Anytime jobs in Chicago, IL? For Remote Anytime jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Anytime jobs in Chicago, IL look for? The top searched job categories for Remote Anytime jobs in Chicago, IL are:
Remote Anytime jobs near you
Infographic showing various Remote Anytime job openings in Chicago, IL as of August 2026, with employment types broken down into 71% Full Time, 28% Part Time, and 1% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $130,860 per year, or $62.9 per hour.

Remote: Contract Specialist III

Planate Management Group

Chicago, IL • On-site, Remote

$80K - $90K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 7 days ago

Job description

Planate Management Group (PMG) is a Service-Disabled Veteran-Owned Small Business (SDVOSB) headquartered in Alexandria, Virginia, and Orlando, Florida USA with a technical support center in South East Asia and East Africa, that provides program management and facilities engineering services worldwide. Planate is a small business provider of planning, design, infrastructure management, technical consulting, engineering, and construction management services in support of the US Department of Defense (DOD) and its Service (Army, Air Force, Navy, Marine Corps) missions, along with other US federal agencies, all over the world.
We are seeking a Contract Specialist III to lead and manage complex federal acquisitions for the Department of Veterans Affairs. This senior-level position requires extensive expertise in contracting, including construction, complex services, and leasing procurements. You will provide advanced acquisition support, offer strategic guidance, ensure compliance with federal regulations, coordinate with stakeholders, and serve as a recognized authority in contracting specialty, demonstrating broad knowledge and skills to effectively execute high-level acquisition responsibilities.
Salary: $80k - $90k/year (range varies depending on experience and qualifications).
Key Responsibilities:
  • Oversee full lifecycle acquisition activities, including pre-award, award, and post-award support for complex contracts.
  • Conduct market research, prepare pre-award notices, and document small business capability analyses.
  • Develop acquisition strategies, Independent Government Cost Estimates (IGCEs), and recommendations for solicitation approaches, options, and risks.
  • Prepare solicitations (RFQs, RFPs, Combined Synopsis/Solicitations) and ensure compliance with FAR, VAAR, and internal VA policies.
  • Assist with proposal and quote evaluations, including price/cost analysis and technical proposal assessments.
  • Prepare and administer contract awards, modifications, option exercises, and close-out documentation.
  • Monitor contractor performance, schedules, compliance with contract terms, and resolve performance issues.
  • Provide guidance, oversight, and mentorship to junior acquisition staff on acquisition planning, documentation, and execution.
  • Maintain accurate contract documentation in the Agency electronic contract management system and report actions into the Federal Procurement Data System (FPDS).
  • Ensure timely and accurate submission of deliverables, including monthly status reports, acquisition milestone trackers, and lessons learned summaries

Qualifications to be successful in the role:
  • Bachelor Degree in Engineering, Business Management, Accountancy
  • Minimum of 6 years of experience in conducting comprehensive acquisition support activities with a working knowledge of Federal Acquisition Regulations (FAR)
  • Specialized experience required for one or more of the following: (at least 3 years developing and administering construction or A-E solicitations and contracts; at least 5 years with complex service solicitations and contracts (e.g., healthcare); at least 2 years developing real property or lease-related solicitations and contracts)
  • FAC-C or DAWIA Level III in Contracting Certification preferred.
  • Demonstrated leadership skills and ability to mentor acquisition staff.
  • Must have stayed/worked in the US within the last 10 years to successfully pass the VA background investigation and obtain a clearance.
  • Must be fluent in English, both written and verbal.

Why Planate?
Planate Management Group is an Affirmative Action and Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or protected veteran status and will not be discriminated against on the basis of disability.
Joining the Planate team opens you to an experience working for a Global company where you are among a team that is considered a premier trusted partner for planning, design, engineering, asset management, and professional service solutions anytime, anywhere. We Take Care of Our Own; Personally, and Profession.
Full-time employees enjoy the following benefits:
  • Medical insurance/Dental/Vision Insurance
  • 401K plan eligibility upon hire
  • Health and Savings Account plan
  • Life/AD&D Insurance Coverage
  • Short-Term Disability Insurance Coverage
  • Paid Holidays
  • Paid Time Off
  • Wellness Offering
  • Training and Development
  • License/Certification support
  • Recognition and Rewards program
  • Travel Insurance

We'd love for you to be a part of our Global workforce, helping us serve as an effective and integrated partner to advance every client's mission!

Apply