Sales Development Representative

Cleo (US) · Chicago, IL

Posted 5/11/2026 · last confirmed live 8/26/2026

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 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 hr@cleo.com. 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.

This role is published by Cleo (US) on greenhouse. SwiftFit is not the employer and does not accept applications.