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Remote Insurance Appointment Setter Jobs in Chicago, IL

Tipton Agency

Insurance Advisor

Chicago, IL · Remote

$60K - $200K/yr

Both part-time and full-time positions are available, allowing you to set your own appointments and ... a remote work environment. Join us at The Tipton Agency and take the first step towards a ...

MeridianLight

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Remote Sales Representative (No Cold Calling, Training Provided)

Chicago, IL · Remote

$60K - $110K/yr

... appointments available (no cold calling) • Remote work / flexible schedule • Training, mentorship, and onboarding support • Access to multiple highly rated insurance carriers • Strong ...

AO Globe Life

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Entry-Level Client Sales Representative (Remote)

Chicago, IL · Remote

$60K - $80K/yr

Meet with clients through scheduled virtual appointments * Present insurance and benefit options ... Ability to work independently in a remote environment * Comfortable using virtual meeting platforms ...

Symmetry

Remote Sales Representative

Chicago, IL · Remote

$75K - $180K/yr

During these virtual appointments, you'll use presentations that have worked well in the past to help clients choose the best insurance program for their family, leveraging remote collaboration ...

Aoglobelife

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Remote Customer Service & Sales Rep (No Experience Needed)

Chicago, IL · Remote

$60K - $80K/yr

You'll meet with clients through **scheduled virtual appointments**, help them understand ... Company Description Globe Life Insurance is an insurance company that specializes in providing ...

Aoglobelife

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Remote Customer Service & Sales Rep (No Experience Needed)

Chicago, IL · Remote

$60K - $80K/yr

You'll meet with clients through **scheduled virtual appointments**, help them understand ... Company Description Globe Life Insurance is an insurance company that specializes in providing ...

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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 Jul 31, 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 July 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $51,976 per year, or $25 per hour.

High Ticket Appointment Setter (Warm Leads)

Curvion Blue

Chicago, IL • Remote

$55K - $65K/yr

Full-time

Re-posted 10 days ago

Job description

Remote | Base + Uncapped Commission | Fast Track to Closing

Most sales reps are underpaid because they’re selling the wrong product, in the wrong environment, with weak lead flow.

At WFS Group, our setters work exclusively warm leads from world class marketing campaigns for high ticket offers ranging from $7k-$15k+.

No cold prospecting lists.
No door knocking.
No guessing who to call.

Your job is simple:
Generate qualified appointments, create pipeline, and feed closers opportunities that turn into revenue.

If you thrive in high output environments, love competition, and want a real path into high ticket closing, this role was built for you.

Why Setters LOVE WFS Group 🚀

  • Fully remote position

  • Warm inbound leads daily

  • Base pay + uncapped commissions

  • Average deal size: $7k-$15k+

  • 10-14 day sales cycle

  • Elite sales training & coaching

  • Clear path to become a closer

  • High performance, competitive culture

  • Products that genuinely change lives

A Snapshot of WFS Group

WFS Group builds and deploys revenue engines for fast growing companies.

We help businesses scale by installing complete sales systems including strategy, automation, pipeline management, recruiting, training, and full sales execution.

Our clients range from SaaS companies to alternative education brands selling transformational programs in business, investing, entrepreneurship, and personal growth.

Put simply:
Companies outsource their sales department to us so they can scale faster.

Position Overview

We’re looking for highly motivated setters who can create momentum, generate excitement, and consistently fill calendars with qualified sales appointments.

This role combines:

  • Warm outbound dialing

  • Inbound lead qualification

  • Pipeline follow up

  • Appointment setting

  • Consultative conversations

You’ll spend most of your day speaking with leads who have already shown interest in our offers through ads, webinars, funnels, social media, or marketing campaigns.

This is not a passive customer support role.

This is a performance driven sales role built for competitive people who want to become elite earners.

You SHOULD Apply If… ✅

  • You’re hungry, competitive, and highly motivated

  • You enjoy phone sales and objection handling

  • You understand sales is a numbers game

  • You want a path into high ticket closing

  • You can handle high volume outbound activity

  • You’re coachable and adaptable

  • You bring energy into conversations naturally

  • You want to be surrounded by ambitious people

You SHOULD NOT Apply If… ❌

  • You dislike structured sales environments

  • You avoid KPIs or performance metrics

  • You struggle with consistency or follow up

  • You need constant supervision

  • You get discouraged easily after rejection

  • You’re uncomfortable on the phones

  • You’re looking for an easy remote job

Responsibilities

  • Make high volume outbound calls to warm leads

  • Qualify prospects and identify buying intent

  • Set appointments for closers

  • Follow up with leads across the pipeline

  • Utilize CRM systems to track activity

  • Attend daily sales meetings and coaching sessions

  • Study sales calls and improve performance

  • Collaborate with closers and leadership

  • Hit and exceed appointment targets consistently

Requirements

  • 6+ months of SDR, setter, or phone sales experience in the high ticket space

  • Strong communication skills

  • Confidence handling objections

  • Ability to work independently remotely

  • Experience using CRM systems

  • High level of personal accountability

  • Strong work ethic and consistency

Compensation

  • Base Pay + Uncapped Commission

  • $55,000-$70,000+ OTE

  • Advancement Opportunities

Schedule

  • Full Time

  • Monday-Friday

  • 9AM-6PM in your U.S. time zone

Compensation Range: $55K - $65K