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Chief Learning Officer Remote Jobs in Chicago, IL

State of Illinois

Chief Medical Officer

Chicago, IL · On-site +1

$225K - $275K/yr

The CMO will report directly to the Medicaid Administrator and build and lead a new clinical ... Flexible work schedules are available in many program areas. (Remote work may be an option for ...

State of Illinois

Chief Medical Officer

Chicago, IL · On-site +1

$225K - $275K/yr

The CMO will report directly to the Medicaid Administrator and build and lead a new clinical ... Flexible work schedules are available in many program areas. (Remote work may be an option for ...

Thomas Management LLC

Chief Growth Officer

Chicago, IL · On-site +1

CHIEF GROWTH OFFICER REAL Food re -fined. Founded in 1986, Thomas Cuisine is an award-winning ... Open to hybrid or fully remote performance. Our commitment to you At Thomas Cuisine, we are ...

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All JobsChief Learning Officer JobsChief Learning Officer Remote JobsChief Learning Officer Remote Jobs in Chicago, IL

Chief Learning Officer Remote information

See Chicago, IL salary details

$42.8K

$155.8K

$277.6K

How much do chief learning officer remote jobs pay per year?

As of Aug 28, 2026, the average yearly pay for chief learning officer remote in Chicago, IL is $155,761.00, according to ZipRecruiter salary data. Most workers in this role earn between $114,900.00 and $190,600.00 per year, depending on experience, location, and employer.

What does a chief learning officer do in a remote role?

A Chief Learning Officer (CLO) in a remote role is responsible for developing and overseeing the learning and development strategy of an organization, often coordinating virtual programs and resources for employees across different locations. They ensure that employees have access to training, skill development, and continuous learning opportunities that align with business goals. The CLO collaborates with leadership, manages learning technologies, and measures the impact of educational initiatives, all while supporting a culture of growth in a virtual work environment.

What are the key skills and qualifications needed to thrive as a chief learning officer in a remote environment?

To thrive as a Chief Learning Officer (CLO) remotely, you need a strong background in learning and development strategy, instructional design, and organizational leadership, often supported by advanced degrees in education, HR, or business. Familiarity with Learning Management Systems (LMS), digital collaboration tools, and data analytics platforms is essential. Outstanding communication, influence, and change management skills help a CLO inspire teams and drive initiatives in virtual settings. These capabilities ensure effective learning cultures, measurable talent development, and alignment with business objectives across distributed organizations.

What are some common challenges faced by a chief learning officer working remotely, and how can they be addressed?

A Chief Learning Officer (CLO) working remotely often faces challenges such as maintaining strong connections with dispersed teams, ensuring consistent learning standards across locations, and effectively communicating the organization’s learning vision. Overcoming these hurdles requires leveraging digital collaboration tools, establishing clear communication channels, and fostering a culture of continuous learning that transcends physical boundaries. Regular virtual check-ins, interactive online training sessions, and data-driven monitoring of learning outcomes are effective strategies to ensure alignment and engagement in a remote environment.

What are the most commonly searched types of Chief Learning Officer jobs in Chicago, IL?

The most popular types of Chief Learning Officer jobs in Chicago, IL are:

What are popular job titles related to Chief Learning Officer Remote jobs in Chicago, IL?

For Chief Learning Officer Remote jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Chief Learning Officer Remote jobs in Chicago, IL look for?

The top searched job categories for Chief Learning Officer Remote jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Chief Learning Officer Remote jobs?

Cities near Chicago, IL with the most Chief Learning Officer Remote job openings:

Chief Learning Officer Remote jobs near you
Infographic showing various Chief Learning Officer Remote job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Part Time. Highlights an 100% Remote job distribution, with an average salary of $155,761 per year, or $74.9 per hour.

Chief Operating Officer - Remote (10256)

Chicago, IL • Remote

Capstone Search Group
Recruiting and Staffing Services • 1 - 10 employees
Learn more about Capstone Search Groupexternal

$200K - $250K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 27 days ago

Job description

About the Role

Unique career opportunity for an experienced health insurance professional as Chief Operating Officer, which is a blend of strategic and tactical responsibilities that positions a TPA for continued growth.


Requires expertise in self-funded healthcare operations, stop-loss programs, and claims management; coming from backgrounds that include benefits admin, payers, or another third-party administrator.


Qualified applicants should possess a well-rounded skill set in areas like:

  • Technology, compliance, claims appeals, and regulation
  • Client service, employee development, and workflow optimization
  • KPI and performance benchmarks around member services and implementation 


Location: Remote. Regular travel to be expected.

Company Description

Capstone Search Group is an insurance recruiting firm that offers creative, unique staffing solutions for the insurance industry! Our clients include insurance companies, agencies, brokers and intermediaries. Our goal as insurance recruiters is to help insurance organizations identify, attract and retain experienced talent that impacts immediate openings and promotes future growth. We offer Direct Hire (Contingency Search, Engaged/Retained and Recruitment Process Outsourcing [RPO]) and Contract Solutions (long-term contract, 1099 and temp-to-perm). We work nationally with expertise that spans top executives, middle management and technical level positions. We are committed to providing recruiting services of the highest degree of confidentiality, professionalism and integrity.