Middleground It

13 Middleground It Jobs Hiring Near You

Middleground is a rapidly growing IT Managed Service Provider located in the Loop. We provide ... Passionate and forward thinking group of IT professionals Professional and city working environment ...

Middleground is a managed IT service provider located in the Chicago area. We are looking for a Marketing Associate to help plan and implement marketing and advertising activities for us and our ...

Hungry desire to succeed and vastly improve IT skills * Ability to work unsupervised and make good use of free time when no help desk is needed Preferred Skills: * Apple Mac OSX experience a plus * 4 ...

Hungry desire to succeed and vastly improve IT skills * Ability to work unsupervised and make good use of free time when no help desk is needed Preferred Skills: * Apple Mac OSX experience a plus * 4 ...

Service Coordinator

Chicago, IL ยท On-site

$20.25 - $25.75/hr

We differ from the other IT companies in Chicago because we deal with both the private and public sector, so your advancement opportunities with our company are greater and broader. We deal with ...

Associate or Bachelor's Degree in CS/IT Microsoft certifications MCSA, MCSE, MCITP, MCP CompTIA A+, Network+, Security+ Cisco certifications CCENT, CCNA, CCNP Microsoft Office 365 Other ...

Service Coordinator

Chicago, IL

$20.25 - $25.75/hr

We differ from the other IT companies in Chicago because we deal with both the private and public sector, so your advancement opportunities with our company are greater and broader. We deal with ...

Associate or Bachelor's Degree in CS/IT Microsoft certifications MCSA, MCSE, MCITP, MCP CompTIA A+, Network+, Security+ Cisco certifications CCENT, CCNA, CCNP Microsoft Office 365 Other ...

Hungry desire to succeed and vastly improve IT skills * Ability to work unsupervised and make good use of free time when no help desk is needed Preferred Skills: * Apple Mac OSX experience a plus * 4 ...

Help Desk II

Chicago, IL ยท On-site

$20.50 - $27.75/hr

We are 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 ...

Help Desk II

Chicago, IL ยท On-site

$20.50 - $27.75/hr

We are 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 ...

Middleground It Jobs Information

Infographic showing various job openings at Middleground It in the United States as of May 2026, with employment types broken down into 86% Full Time, and 14% Part Time. Highlights an 86% Physical, and 14% Remote job distribution.

Sales Representative

Middleground It

Chicago, IL โ€ข On-site

Full-time

Posted 3 days ago


Job description

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 objectives
  • Partner with Sales Executives to call on targeted account lists, build relationships with key decision makers to identify project and business needs
  • Achieve quarterly lead generation and conversion goals set by sales management
  • Proactively call into accounts on targeted lists by utilizing and maintaining corporate database
  • Desire to achieve and exceed sales goals- self starting attitude is critical
  • Ability to be creative, resourceful and autonomous in a start-up environment
  • Maintain complete and accurate records of all activity throughout the marketing development cycle in Connectwise and Hubspot
  • Maintain strong relationship with sales team through clear communication and follow-up

2) Internal Communication:
  • Facilitate communication between Marketing and Sales, particularly to help improve the lead-qualification criteria, process, and tools
  • Provide feedback to the Marketing team on quality of inquiries/leads obtained through various Marketing/Sales vehicles and provide input for future campaigns and promotions
  • Continually improve the quality of the marketing database by updating records to ensure accurate account and contact information

3) 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 meetings
  • Stay current on industry trends and maintain knowledge of competitors' product offerings

Requirements & Preferred Skills
  • Bachelor's degree is preferred
  • 0-2 years' experience in a B2B business sales "hunting role"
  • 1+ years' experience with customer service, inbound and outbound telesales, or market development activities
  • Excellent oral, written and presentation skills
  • "Thick skin" and ability to push forward consistently regardless of objections
  • Well organized, with the ability to prioritize tasks and manage time effectively
  • Ability to penetrate accounts and nurture potential opportunities
  • Understanding of consultative sales process
  • Active listening skills
  • Proven problem solver with a strong desire to learn
  • Self-motivated with an entrepreneurial spirit
  • Strong research skills
  • Experience using a CRM - Hubspot a plus
  • Interest and excitement around technology and the sales professional

This will be a W2 salary position.
Passionate and forward thinking group of IT professionals
Professional and city working environment
Ideal candidate will live closer to the downtown Chicago
Please, no recruiters.
Please, do not call us about this position.