ZipRecruiter

Log In

2

Remote Outbound Sales Jobs in Chicago, IL (NOW HIRING)

AMBA

Inside Sales Insurance Specialist

Naperville, IL · Remote

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

AMBA

Inside Sales Insurance Specialist

Naperville, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

AMBA

Inside Sales Insurance Specialist

Naperville, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Inside Sales Insurance Specialist (W2, Remote) Full-Time | Monday through Friday Compensation ... Consistent outbound activity is the primary driver of success in this position. About AMBA AMBA ...

Melio

Sales Development Representative

Chicago, IL · On-site +1

$60K - $63K/yr

Remote (required to live in one of the following states: AZ, CO, FL, GA, IL, MI, MN, NY, NC, TX, UT,VT) Qualifications: * 1+ year of dedicated experience in an Outbound Sales Development or Business ...

Staples, Inc.

Inside Sales Manager

Schaumburg, IL · On-site +1

... remote work on Fridays. Join a team that powers everyday impact. Quill, a proud member of the ... Make outbound sales calls to engage customers, expand relationships, and uncover new business ...

Staples, Inc.

Sales Account Manager

Waukegan, IL · On-site +1

... remote work on Fridays. Join a team that powers everyday impact. Quill, a proud member of the ... Make outbound sales calls to engage customers, expand relationships, and uncover new business ...

next page

Showing results 1-20

All JobsOutbound Sales JobsRemote Outbound Sales JobsRemote Outbound Sales Jobs in Chicago, IL

Remote Outbound Sales information

See Chicago, IL salary details

$11

$23

$42

How much do remote outbound sales jobs pay per hour?

As of Sep 1, 2026, the average hourly pay for remote outbound sales in Chicago, IL is $23.52, according to ZipRecruiter salary data. Most workers in this role earn between $15.34 and $23.51 per hour, depending on experience, location, and employer.

What is a remote outbound sales?

Remote Outbound Sales jobs involve contacting potential customers via phone, email, or other online platforms to generate leads, promote products or services, and secure sales—all while working from a remote location. Professionals in these roles are responsible for reaching out to prospects, understanding their needs, providing information, and closing deals. Success in remote outbound sales typically requires strong communication skills, self-motivation, and the ability to work independently. These positions often use customer relationship management (CRM) software to track interactions and sales progress, and may have performance targets or quotas to meet.

What are the key skills and qualifications needed to thrive as a remote outbound sales professional?

To excel as a Remote Outbound Sales professional, you need strong communication, persuasion, and negotiation skills, often supported by a background in sales or business and familiarity with CRM software. Proficiency with tools like Salesforce, HubSpot, and virtual meeting platforms is typically required. Self-motivation, resilience, and active listening are critical soft skills for building rapport and handling rejection. These abilities enable sales professionals to effectively reach prospects, close deals, and achieve targets from a remote environment.

What are some common challenges faced by remote outbound sales professionals, and how can they be overcome?

Remote outbound sales professionals often encounter challenges such as building rapport with prospects over the phone or video, managing time effectively without in-person supervision, and staying motivated in a virtual environment. To overcome these, it's important to establish a structured daily routine, utilize CRM tools to track outreach and follow-ups, and participate in regular team meetings to maintain connection with colleagues. Additionally, focusing on active listening and personalizing conversations can help foster stronger relationships with potential clients.

What is the difference between Remote Outbound Sales vs Remote Inbound Sales?

AspectRemote Outbound SalesRemote Inbound Sales
Primary FocusProactively reaching out to potential clientsResponding to incoming customer inquiries
Work EnvironmentCold calling, prospecting, lead generationHandling inbound calls, customer support
Required SkillsCommunication, persuasion, lead qualificationCustomer service, product knowledge, problem-solving
Common Industry UsageSales teams, telemarketing, B2B salesCustomer support, service departments

Remote Outbound Sales involves actively reaching out to potential clients to generate sales, while Remote Inbound Sales focuses on responding to incoming customer inquiries. Both roles require strong communication skills but differ in their approach and daily tasks. Understanding these differences helps job seekers find the right position aligned with their skills and career goals.

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

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

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

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

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

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

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

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

Remote Outbound Sales jobs near you
Infographic showing various Remote Outbound Sales job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, 21% Part Time, 1% Contract, and 1% Nights. Highlights an 76% Physical, 1% Hybrid, and 23% Remote job distribution, with an average salary of $48,930 per year, or $23.5 per hour.

Sales Development Representative (SDR) - Freight & Logistics

Chicago, IL • Remote

Fox Carriers
Transportation and Warehousing • 11 - 50 employees
Learn more about Fox Carriersexternal

$15 - $20/hr

Full-time

Re-posted 17 days ago

Job description

Sales Development Representative (SDR) – Remote

Work from Anywhere | $20/hr | Freight & Logistics

About GetCarrier:
We’re a fast-growing logistics company specializing in drayage, LTL, and expedited freight. From port to final mile, we keep freight moving. Now we’re building our outbound sales team and looking for motivated SDRs ready to have real conversations and book qualified meetings.

What You’ll Be Doing:
  • Make 300-400 outbound calls per day using our dialer.
  • Start conversations with logistics managers, warehouse supervisors, and operations teams.
  • Book Zoom calls for our account managers.
  • Share wins and challenges in daily SDR team huddles.

What You’ll Learn:
  • How drayage, LTL, and expedited shipping work.
  • How to connect with decision-makers in logistics and supply chain.
  • How to grow a career in freight sales.

What We’re Looking For:
  • Strong spoken English and confident phone presence.
  • Comfortable with rejection and fast-paced calling.
  • Organized, coachable, and goal-driven.
  • Sales or logistics experience is a plus, but not required.

Compensation:
  • $20/hour contractor role (managed via Squad).
  • 100% remote.
  • Appointment bonuses.

Why GetCarrier:
We’re not just another freight brokerage. We use real carrier networks, offer competitive rates, and build trust with every shipment. If you’re hungry to learn and ready to hustle, this is your chance to grow in logistics and sales.

Apply now to join the team!
Fox Carriers logo

About Fox Carriers

Sourced by ZipRecruiter

Fox Carriers is an experienced Professional Logistics Company. We have expanded and opened a direction with a database of 7 Car Hauler trucks. We offer a wide range of car delivery solutions. Provide you with Accurate and Competitive shipping prices for one of our machines. Timing and Attention to detail are in our DNA so we treat every shipment with special care.Our goal is to make the delivery process simple and smooth, no matter how many bumps in the road.

Industry

Transportation and warehousing

Company size

11 - 50 Employees

Headquarters location

Stamford, CT, US

Social media

FacebookInstagram

View All Fox Carriers Jobs