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Remote Insurance Appointment Setter Jobs in Chicago, IL

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... While leads are provided, this is not an inbound or appointment-setting role . Consistent outbound ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... While leads are provided, this is not an inbound or appointment-setting role . Consistent outbound ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... While leads are provided, this is not an inbound or appointment-setting role . Consistent outbound ...

Healthpilot Technologies LLC

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Independent Medicare Agent (Remote)

Chicago, IL · Remote

$104K - $136K/yr

Client-facing needs assessment captures drugs, doctors, and preferences before your appointment ... Active Health Insurance License in your resident state * AHIP 2026 certification (or willing to ...

AO Globe Life

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Entry Level Sales Associate (Remote)

Chicago, IL · Remote

$60K - $80K/yr

Previous insurance or sales experience is not required. Important Location Requirement This remote ... Ability to participate in scheduled virtual meetings and client appointments About AO Globe Life AO ...

Aoglobelife

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Remote Customer Sales Rep Entry Level (No Experience Welcome to Apply)

Chicago, IL · Remote

$60K - $80K/yr

This is a fully remote position with scheduled appointments--* no cold calling or door-to-door ... Medical Insurance for you and your family * Life Insurance for you and your family What We're ...

Aoglobelife

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Remote Customer Sales Rep Entry Level (No Experience Welcome to Apply)

Chicago, IL · Remote

$60K - $80K/yr

This is a fully remote position with scheduled appointments--* no cold calling or door-to-door ... Medical Insurance for you and your family * Life Insurance for you and your family What We're ...

Aoglobelife

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Remote Customer Sales Rep Entry Level (No Experience Welcome to Apply)

Chicago, IL · Remote

$60K - $80K/yr

This is a fully remote position with scheduled appointments--* no cold calling or door-to-door ... Medical Insurance for you and your family * Life Insurance for you and your family What We're ...

PainPoint

Customer Service Representative

Chicago, IL · On-site +1

$18/hr

Remote Looking for a rewarding career where you can make an impact every day? Join DxTx Pain ... Reschedule, cancel, and confirm appointments as needed * Provide excellent, timely customer service

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All JobsInsurance Appointment Setter JobsRemote Insurance Appointment Setter JobsRemote Insurance Appointment Setter Jobs in Chicago, IL

Remote Insurance Appointment Setter information

See Chicago, IL salary details

$10

$24

$44

How much do remote insurance appointment setter jobs pay per hour?

As of Aug 20, 2026, the average hourly pay for remote insurance appointment setter in Chicago, IL is $24.99, according to ZipRecruiter salary data. Most workers in this role earn between $16.35 and $30.72 per hour, depending on experience, location, and employer.

What is the difference between Remote Insurance Appointment Setter vs Remote Insurance Customer Service Representative?

AspectRemote Insurance Appointment SetterRemote Insurance Customer Service Representative
Primary RoleScheduling insurance appointments and consultationsHandling customer inquiries, policy support, and claims assistance
Required SkillsCommunication, scheduling, basic insurance knowledgeCustomer service, problem-solving, insurance product knowledge
Work EnvironmentRemote, client-facing, appointment-focusedRemote, customer support, communication-heavy
CertificationsNone typically required, insurance knowledge preferredCustomer service experience, insurance knowledge beneficial

The main difference is that Remote Insurance Appointment Setters focus on scheduling appointments for insurance agents or brokers, while Remote Insurance Customer Service Representatives handle ongoing customer inquiries and support. Both roles often require strong communication skills and insurance knowledge, but their daily tasks and objectives differ significantly.

What are the most commonly searched types of Insurance Appointment Setter jobs in Chicago, IL?

The most popular types of Insurance Appointment Setter jobs in Chicago, IL are:

What are popular job titles related to Remote Insurance Appointment Setter jobs in Chicago, IL?

For Remote Insurance Appointment Setter jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Insurance Appointment Setter jobs in Chicago, IL look for?

The top searched job categories for Remote Insurance Appointment Setter jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Insurance Appointment Setter jobs?

Cities near Chicago, IL with the most Remote Insurance Appointment Setter job openings:

Remote Insurance Appointment Setter jobs near you
Infographic showing various Remote Insurance Appointment Setter job openings in Chicago, IL as of August 2026, with employment types broken down into 57% Full Time, and 43% Part Time. Highlights an 100% Remote job distribution, with an average salary of $51,976 per year, or $25 per hour.

Inside Sales Insurance Specialist

AMBA

Chicago, IL • Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 8 days ago

Job description

Inside Sales Insurance Specialist (W2, Remote)
Full-Time | Monday through Friday
Compensation: Hourly base plus performance bonuses
License: Life and Health preferred
 
Important Role Overview
This is a high-volume outbound calling role in a structured inside sales environment. Successful candidates are comfortable spending the majority of their workday actively dialing, following up, and converting member conversations into enrollments.
 
While leads are provided, this is not an inbound or appointment-setting role. Consistent outbound activity is the primary driver of success in this position.
 
About AMBA
AMBA partners with public employee, alumni, and professional occupation associations nationwide to deliver Life and Supplemental Health insurance benefits to their members. We work with some of the most significant retired public employee associations in the country, supporting millions of members across all 50 states.
 
As an Inside Sales Insurance Specialist, you will engage existing members and policyholders to educate them on benefit options and enroll them in coverage that meets their needs.
 
What You Will Do
  • Make 150 or more outbound calls per day using company-provided lead lists
  • Spend the majority of your workday actively dialing, speaking with members, and following up
  • Deliver scripted and consultative sales presentations over the phone
  • Educate members on supplemental Life and Health insurance products and complete enrollments
  • Manage inbound calls as volume allows, with outbound calling remaining the primary responsibility
  • Accurately document all activity in Salesforce and manage a personal sales pipeline
  • Meet daily activity expectations and monthly performance goals
  • Provide a professional, compliant, and member-focused experience on every call
Work Environment
This role operates in a structured, metrics-driven call center environment with clear daily expectations for outbound call volume, talk time, conversions, and documentation accuracy. Success requires consistency, resilience, and comfort with repetition.
 
This Role Is a Strong Fit If You
  • Have experience in a high-volume outbound sales or call center role
  • Are comfortable making frequent outbound calls throughout the day
  • Understand that leads support the work, but dialing drives results
  • Are motivated by structure, accountability, and measurable goals
  • Can handle phone-based rejection while maintaining professionalism
  • Are seeking a stable W2 role with performance-based earning potential
This Role May Not Be a Fit If You
  • Prefer inbound-only or appointment-based sales roles
  • Are uncomfortable with frequent dialing or high daily call expectations
  • Need a highly flexible or unstructured workday
  • Are looking for an account management or relationship-only role
What You Bring
  • Active Life and Health insurance license preferred. Candidates without an active license must be willing and able to obtain licensure within a defined onboarding timeframe.
  • Two or more years of insurance sales or high-volume call center experience preferred
  • Strong communication, listening, and objection-handling skills
  • Comfort working in a fast-paced, goal-driven environment
  • Technical proficiency with CRM tools. Salesforce experience is a plus
  • Reliability, resilience, and a consistent work ethic
Compensation and Benefits
  • Hourly base pay plus monthly performance bonuses
  • Typical first-year earnings range from $50,000 to $60,000
  • Top performers earn $100,000 or more
  • Comprehensive benefits package including medical, dental, vision, life, and long-term disability coverage
  • 401(k) with company match
  • Paid time off and paid holidays
  • Career development, coaching, and internal advancement opportunities
Apply Today
If you are licensed, comfortable with high-volume outbound calling, and ready to build a stable inside sales career with strong earning potential, we invite you to apply today. 
 
AMBA is proud to be an Equal Opportunity Employer.