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Freelance Sales Development Representative Jobs in Illinois

Cleo

Sales Development Representative

Chicago, IL · On-site

$65K/yr

As a Sales Development Representative, you will play a critical role in supporting the organization's significant growth while identifying new opportunities for Cleo within prospective accounts.

Canonical

Sales Development Representative

Chicago, IL · Remote

The role of a Sales Development Representative at Canonical Canonical is profitable and growing. We consider our sales development organization to be the best technology sales academy in the market ...

Corgi

Sales Development Representative

Mundelein, IL · On-site

Role Description This is a full-time, on-site role based in San Francisco for a Sales Development Representative on our trucking insurance team. You will work directly with the two executives leading ...

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Gong.io

Sales Development Representative

Chicago, IL · On-site +1

$90K/yr

As a Gong Sales Development Representative, you'll play a key role in generating new business opportunities for the company and be a part of building a world-class sales development organization at a ...

AwardSpring

Sales Development Representative

Chicago, IL · On-site +1

$45K - $55K/yr

Job Overview The Sales Development Representative role will focus on prospecting and generating new business opportunities to support AwardSpring's growth. This role involves value-based outreach to ...

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Freelance Sales Development Representative information

What are the key skills and qualifications needed to thrive as a Freelance Sales Development Representative, and why are they important?

To excel as a Freelance Sales Development Representative, you need excellent prospecting, lead generation, and communication skills, often supported by experience in sales or a related field. Familiarity with CRM software (like Salesforce or HubSpot), email automation tools, and online meeting platforms is typically required. Outstanding self-motivation, resilience, and strong interpersonal skills help build relationships and adapt to varied client needs. These competencies are crucial for consistently generating qualified leads, meeting targets, and succeeding in the flexible, self-driven freelance environment.

How does a Freelance Sales Development Representative typically manage client relationships and balance multiple accounts?

As a Freelance Sales Development Representative, you are often responsible for juggling several client accounts simultaneously. Success in this role relies on excellent time management, clear communication, and the ability to quickly understand each client's unique goals and sales processes. You'll regularly coordinate with your clients' internal sales or marketing teams to align strategies, track lead progress, and report on outreach efforts. Building strong, transparent relationships with clients is key to ensuring repeat business and long-term partnerships.

What are Freelance Sales Development Representatives?

Freelance Sales Development Representatives (SDRs) are independent professionals who help businesses identify and qualify sales leads. Unlike full-time, in-house SDRs, freelancers work on a contract basis and often support multiple clients by conducting outreach, following up on prospects, and setting appointments for sales teams. They use various channels such as email, phone calls, and social media to generate interest in a company's products or services. Freelance SDRs are valued for their flexibility and ability to quickly scale sales efforts without the long-term commitment of hiring full-time staff.

What is the difference between Freelance Sales Development Representative vs Inside Sales Representative?

AspectFreelance Sales Development RepresentativeInside Sales Representative
Work EnvironmentRemote, independent, freelance basisTypically in-office or remote, employed by a company
CredentialsSales experience, communication skills, sometimes certificationsSales experience, often with company-specific training
Employer & Industry UsageFreelance platforms, startups, B2B salesCorporate sales teams, B2B and B2C sectors
Work FocusLead generation, outreach, qualifying prospectsClosing sales, account management, customer retention

In summary, a Freelance Sales Development Representative works independently to generate and qualify leads remotely, often on a project basis, while an Inside Sales Representative is typically employed by a company to handle sales activities within the organization, focusing on closing deals and maintaining client relationships.

What are the most commonly searched types of Sales Development Representative jobs in Illinois? The most popular types of Sales Development Representative jobs in Illinois are:
What are popular job titles related to Freelance Sales Development Representative jobs in Illinois? For Freelance Sales Development Representative jobs in Illinois, the most frequently searched job titles are:
What job categories do people searching Freelance Sales Development Representative jobs in Illinois look for? The top searched job categories for Freelance Sales Development Representative jobs in Illinois are:
What cities in Illinois are hiring for Freelance Sales Development Representative jobs? Cities in Illinois with the most Freelance Sales Development Representative job openings:
Freelance Sales Development Representative jobs near you
Sales Development Representative

Sales Development Representative

Cleo (US)

Chicago, IL

$65K/yr

Other

Medical, Dental, Vision, Life, Retirement, PTO

Posted 2 days ago

Job description

At Cleo, we are not only passionate about helping our customers reach success, but we are also passionate about our team members. We foster innovation in a thriving, high-velocity work environment. Our team members are among the best and the brightest, working in an environment where strategy, technology, and marketing intersect to create amazing products.

We are looking for builders, innovators, and fast-trackers to join our talented marketing and sales team.

As a Sales Development Representative, you will play a critical role in supporting the organization's significant growth while identifying new opportunities for Cleo within prospective accounts. Reporting to Cleo's Manager of Sales Development, you will be tasked with initiating sales cycles and developing millions of dollars in pipeline for our Sales Team through strategic prospecting and AI-powered outreach. You will become a Cleo product expert, including fluency in Cleo's AI-driven ecosystem integration capabilities and develop the necessary skills to enjoy a future sales role here at Cleo. This role will require a high level of outbound activity, organization, and smart use of AI tools to maximize your impact.

If you are looking for a career in high-tech/software sales (not just another boring job), then this is the right role for you.

What You Will Be Doing
  • Work in parallel with assigned Account Executive to identify and prospect in-market net new accounts
  • Generate new business opportunities through outbound campaign activities, including cold-calling, email, and social selling
  • Collaborate with Marketing to drive necessary content creation and any other collateral that will assist in breaking through to targeted accounts
  • Continuously improve knowledge of products, industry trends, and sales techniques to enhance sales development skills
  • Thoroughly qualify prospects to ensure there is a good fit between Cleo and prospective accounts
  • Inspire prospects and create a sense of urgency through clear articulation of Cleo's value proposition and pain-based selling
  • Consistently achieve or exceed monthly opportunity targets
  • Attain monthly outbound activity expectations for dials, emails, and total touches against targeted accounts
  • Leverage AI-powered intent data and buying signal platforms to prioritize the highest-propensity accounts and personalize outreach at scale
  • Effectively craft tailored messaging for specific accounts based on digital activity identified across multiple platforms, including AI-generated insights surfaced through Cleo's sales tool stack
  • Use AI-assisted research and account intelligence tools (e.g., ZoomInfo, Clay, 6sense, or similar) to build hyper-targeted prospect lists and uncover relevant triggers before outreach
  • Become proficient in Cleo's modern sales tech stack: sales engagement and nurturing platforms, AI-powered buying intent tools, and account-based orchestration platforms
  • Be part of one of the best on-the-job SaaS sales training programs in the industry, including hands-on enablement on how to sell Cleo's AI-driven integration platform
Your Qualifications
  • Have received a bachelor's degree
  • At least one year of related sales experience, demonstrating ability to thrive in a hunter-like sales role
  • Effective verbal and written communication skills
  • Focus on the positive and strive for continual improvement
  • Be results-oriented and driven to carve out a career path within the field of sales
  • Display a strong interest in supply chain trends and technology, including how AI and automation are reshaping B2B integration and logistics
  • Collaborate and operate well in a fast-paced, team-oriented environment
  • Be a quick learner with the ability to solve complex problems
  • Adhere to a strong work ethic and maintain a positive outlook
  • Enjoy learning about the IT / Software industry
  • Comfort using AI tools for prospecting, research, and communication to work smarter and maximize outbound output
  • Local candidates only - This role is On-site
 A few things we have to offer: 
  • $65,000 annual salary + commission opportunity 
  • Great Healthcare + Dental + Vision
  • Flexible PTO
  • Culture of support, encouraging Life-Work balance
  • 401k match
  • FSA and HSA options
  • Employee Assistance Program
  • Paid Parental Leave
  • Representing a company with 4,000+ clients and a 99% retention rate
  • Accelerated title and salary growth potential 
  • A fun and energetic work environment that makes you excited to go to work every day

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