Sales Development Representative New Chicago, Illinois

Cleo; Chicago (IL); On-site; USD 59,000 - 72,000; Full time

Benefits offered by this job

65,000 USD annual salary + commission

Great Healthcare + Dental + Vision

Flexible PTO

Culture of support

FSA and HSA options

Employee Assistance Program

High client base with 4,000+ clients

Accelerated title and salary growth

Energetic work environment

Job summary

Cleo is seeking a Sales Development Representative in Chicago to drive growth by initiating sales cycles and building multi-million dollar pipelines through strategic prospecting and AI-powered outreach. You will become a Cleo product expert and collaborate with an on-site team to maximize outbound impact.

The role emphasizes high activity, strong organization, and continuous learning in a fast-paced SaaS environment. Local candidates and on-site presence are required.

Qualifications

• Bachelor’s degree required.
• At least 1 year of related sales experience.
• Strong verbal and written communication skills.
• Results-oriented and career-focused in sales.

Responsibilities

• Work with Account Executive to identify and prospect in-market net new accounts.
• Generate new business opportunities via outbound campaigns (cold calls, email, social).
• Collaborate with Marketing to create content and collateral for targeted accounts.
• Qualify prospects to ensure a fit with Cleo’s value proposition.
• Achieve monthly opportunity targets and outbound activity goals.
• Leverage AI-powered intent data to prioritize high-propensity accounts.
• Craft tailored messaging based on digital activity and AI insights.
• Utilize AI-assisted research tools to build hyper-targeted lists.

Skills

Outbound sales

Cold calling

Email outreach

Social selling

Prospecting

AI-enabled outreach

Education

Bachelor’s degree

Tools

ZoomInfo

Clay

6sense

Job description

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.

• 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
• Know when and how to use AI in the prospecting workflow: decide which tasks to delegate to AI (research, list building, first-draft messaging, call prep, follow-up) and which require human judgment and relationship-building
• Speak credibly with prospects about how AI and automation are transforming B2B integration and supply chain operations, and connect those trends to Cleo’s platform
• Stay curious and adaptable: proactively experiment with new AI tools and features, and keep your skills current as the technology evolves

Prerequisites

• 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 offer

• $65,000 annual salary + commission opportunity
• Great Healthcare + Dental + Vision
• Flexible PTO
• Culture of support, encouraging Life-Work balance
• FSA and HSA options
• Employee Assistance Program
• 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

We use artificial intelligence (AI) tools to assist in certain stages of our recruitment process, such as resume screening and candidate matching. These tools are designed to support fair and consistent evaluations. If you have questions about this process or would like to request an alternative assessment method, please contact us at [e-mail].

Cleo Communications US, LLC is an equal opportunity/affirmative action employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability status, protected veteran status, or any other characteristic protected by law.

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Cleo (US) ’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection.As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measurethe effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categoriesis as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.