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Sales Representative
Chicago, ILMarch 27th, 2026
Middleground is a rapidly growing IT Managed Service Provider located in the Loop. We provide outsourced IT services to clients in the Chicago area, including industries such as Healthcare, Legal, Financial, Manufacturing, Federal Government, and many more. We are very fast paced and this position requires quick thinking and a "can do" attitude.As the Sales Representative, you will play a vital role in the growth of our sales pipeline. You will identify and qualify sales opportunities, partner with our sales team to determine the accounts that require penetrating, target those accounts, respond to inbound leads, and set initial appointments. This role will encompass research, cold calling, collaboration, time management, pipeline development, and thorough communication.Key Accountabilities:1) Lead & Appointment Generation:Directly responsible and accountable for producing qualified leads and appointments between the prospects and sales personnel to assist in meeting company objectivesPartner with Sales Executives to call on targeted account lists, build relationships with key decision makers to identify project and business needsAchieve quarterly lead generation and conversion goals set by sales managementProactively call into accounts on targeted lists by utilizing and maintaining corporate databaseDesire to achieve and exceed sales goals- self starting attitude is criticalAbility to be creative, resourceful and autonomous in a start-up environmentMaintain complete and accurate records of all activity throughout the marketing development cycle in Connectwise and HubspotMaintain strong relationship with sales team through clear communication and follow-up2) Internal Communication:Facilitate communication between Marketing and Sales, particularly to help improve the lead-qualification criteria, process, and toolsProvide feedback to the Marketing team on quality of inquiries/leads obtained through various Marketing/Sales vehicles and provide input for future campaigns and promotionsContinually improve the quality of the marketing database by updating records to ensure accurate account and contact information3) Continuous Learning & Professional Development:Maintain up-to-date knowledge on all Middleground service offerings through marketing materials, enablement resources, and participation in service demonstrations & client meetingsStay current on industry trends and maintain knowledge of competitors' product offeringsRequirements & Preferred SkillsBachelor's degree is preferred0-2 years' experience in a B2B business sales "hunting role"1+ years' experience with customer service, inbound and outbound telesales, or market development activitiesExcellent oral, written and presentation skills"Thick skin" and ability to push forward consistently regardless of objectionsWell organized, with the ability to prioritize tasks and manage time effectivelyAbility to penetrate accounts and nurture potential opportunitiesUnderstanding of consultative sales processActive listening skillsProven problem solver with a strong desire to learnSelf-motivated with an entrepreneurial spiritStrong research skillsExperience using a CRM - Hubspot a plusInterest and excitement around technology and the sales professionalThis will be a W2 salary position.Passionate and forward thinking group of IT professionalsProfessional and city working environmentIdeal candidate will live closer to the downtown ChicagoPlease, no recruiters.
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