1

Flexible Inbound Sales Development Representative Jobs in Chicago, IL

Manager, Inbound Sales Development

Schaumburg, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Position Overview This role is a key leadership role responsible for leading a team of Sales Development Representatives (SDRs) focused on converting inbound demand into qualified sales opportunities.

Manager, Inbound Sales Development

Schaumburg, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

Position Overview This role is a key leadership role responsible for leading a team of Sales Development Representatives (SDRs) focused on converting inbound demand into qualified sales opportunities.

... Sales Development Representative to join our growing Sales Team based out of our Chicago Office ... Identify and qualify new inbound sales opportunities for Flexport * Partner closely with marketing ...

Sales Development Representative

Chicago, IL · On-site

  • Medical

  • Dental

  • Vision

  • Retirement

As a Sales Development Representative, you will drive a strategic outbound and inbound pipeline across the US market. You won't just book meetings - you'll create meaningful business opportunities.

At LinkedIn, our approach to flexible work is centered on trust and optimized for culture ... Qualify and develop inbound and/or outbound sales leads Run campaigns to generate new sales ...

next page

Showing results 1-20

Flexible Inbound Sales Development Representative information

See Chicago, IL salary details

$9

$21

$37

How much do flexible inbound sales development representative jobs pay per hour?

As of Aug 18, 2026, the average hourly pay for flexible inbound sales development representative in Chicago, IL is $21.04, according to ZipRecruiter salary data. Most workers in this role earn between $15.87 and $24.76 per hour, depending on experience, location, and employer.

What is the difference between Flexible Inbound Sales Development Representative vs Inbound Sales Representative?

AspectFlexible Inbound Sales Development RepresentativeInbound Sales Representative
Primary RoleQualifies inbound leads, initiates contact, and sets appointmentsHandles inbound inquiries, nurtures leads, and closes sales
Work EnvironmentFlexible, often remote, with a focus on lead qualificationTypically office-based or hybrid, focusing on closing sales
Required SkillsCommunication, lead qualification, CRM proficiencyCustomer engagement, product knowledge, closing skills

The Flexible Inbound Sales Development Representative primarily focuses on qualifying inbound leads and setting appointments, often with flexible or remote work arrangements. In contrast, the Inbound Sales Representative handles inbound inquiries, nurtures leads, and works towards closing sales. Both roles require strong communication skills and familiarity with CRM tools, but their core responsibilities differ in the sales process. Understanding these distinctions helps organizations assign the right roles for effective sales pipelines.

What are the most commonly searched types of Inbound Sales Development Representative jobs in Chicago, IL?

The most popular types of Inbound Sales Development Representative jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Flexible Inbound Sales Development Representative jobs?

Cities near Chicago, IL with the most Flexible Inbound Sales Development Representative job openings:

Inbound Sales Development Representative

Paylocity

Schaumburg, IL • On-site

$47K - $50K/yr

Other

This job post has expired today. Applications are no longer accepted.


Paylocity rating

7.8

Company rating: 7.8 out of 10

Based on 70 frontline employees who took The Breakroom Quiz

148th of 492 rated business services


Job description

Inbound Sales Development Representative

Paylocity is an award-winning provider of cloud-based HR and payroll software solutions, offering the most complete platform for the modern workforce. The company has become one of the fastest-growing HCM software providers worldwide by offering an intuitive, easy-to-use product suite that helps businesses automate and streamline HR and payroll processes, attract and retain talent, and build a strong workplace culture.

Inbound Sales Development Representatives (ISDRs) are a crucial part of Paylocity's sales organization, responsible for managing and qualifying inbound leads. As the first point of contact, you will engage with prospects who have expressed interest in our payroll and HR solutions, helping them understand how Paylocity can support their business.

Primary responsibilities include:

  • Engage & qualify inbound leads
    • Respond to inbound inquiries via phone, email, website forms, and live chat with speed and professionalism to maximize conversion rates
    • Use a consultative sales approach to understand business needs and align them with Paylocity's solutions
    • Overcome objections and effectively communicate Paylocity's value proposition
  • Optimize lead flow & sales handoff
    • Qualify and route inbound leads to the appropriate sales teams, ensuring seamless transitions
    • Set up sales meetings by positioning our solutions as a fit for the prospect's needs
    • Maintain a high standard for lead response time, ensuring timely engagement with all prospects
  • Enhance the client experience
    • Build rapport with prospects, creating a positive first impression of Paylocity.
    • Provide real-time responses to inquiries via website chat to maximize engagement.
    • Support existing clients looking to expand services by directing them to the right teams.
  • Leverage technology & sales tools
    • Maintain accurate records in CRM systems (SalesLoft, Salesforce etc.) to track interactions and follow-ups.
    • Analyze trends from inbound inquiries and provide feedback on campaigns, messaging effectiveness, and market dynamics to help optimize sales strategies.
    • Stay informed on Paylocity's services, sales tools, and industry trends to provide knowledgeable responses.

Education and experience:

  • Bachelor's degree preferred or equivalent work experience
  • 1+ years of experience in payroll, HR, sales, or customer-facing roles
  • Strong verbal and written communication skills with a consultative approach
  • Excellent time management and organizational skills
  • Ability to adapt to a fast-paced, team-oriented environment
  • Tech-savvy with proficiency in CRM tools, MS Office, and sales engagement platforms
  • A growth mindset with the ability to receive and implement feedback

Physical requirements:

  • Ability to sit for extended periods: The role requires sitting at a desk or workstation for long periods, typically 7-8 hours a day
  • Use of computer and phone systems: The employee must be able to operate a computer, use phone systems, and type. This includes using multiple software programs and inquiries simultaneously.

Paylocity is an equal-opportunity employer. Paylocity is committed to the full inclusion of all individuals. We recruit, train, compensate, and promote regardless of race, religion, color, national origin, sex, disability, age, veteran status, and other protected status as required by applicable law. At Paylocity, we believe diversity makes us better.

We embrace and encourage our employees' differences in age, culture, ethnicity, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion or spiritual belief, sexual orientation, socio-economic status, veteran status, and other characteristics that make our employees unique. We actively cultivate these differences through our employee resource groups (ERGs), employee experiences, perspectives, talents, and approaches to drive innovation in the software and services we provide our customers.

The base pay range for this position $47,000/yr - $50,000/yr; however, base pay offered may vary depending on job-related knowledge, skills, and experience. This position is eligible for our variable commission plan and offers a full range of benefits outlined here. This information is provided per the relevant state and local pay transparency laws for the location in which this position will be performed. Base pay information is based on market location.


What Paylocity employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom