Inside Sales Representative

A company focused on positive change 

Webit Services is one of the leading Managed Services Providers in Chicago.  Our company has been honored to receive the Better Business Bureau’s Torch Award for Ethics not once, but twice since 2019.  We are the only Employee-Owned MSP in the region.  Our consistency has led to this opportunity.  We are looking to expand and in the Inside Sales Representative role, you will be on the ground floor of a new sales team.  This role will be the next component of a scalable, repeatable sales engine and we are looking for professionals who want to win and who have a sense of urgency to do so. 

The Role 

We are seeking a world-class Inside Sales Representative to generate high-quality appointments for our sales team.  Motivated by the knowledge that the services we sell are directly responsible for empowering clients, Inside Sales Executives exceed sales goals and break into Chicago’s most influential small and medium sized businesses. 

You will be responsible for finding and pursuing new business opportunities within targeted accounts in the Chicago area.  Each client is different and has their own current approach to handling their IT support and strategy.  Inside Sales Representatives will use these differences as opportunities to explore improved IT solutions with prospective clients and generate high-quality appointments for our sales team. 

Core Responsibilities: 

• Generate appointments through outbound cold calling and emailing campaigns. 

• Qualify leads based on predetermined criteria and interest in our products/services. 

• Effectively communicate value propositions and overcome objections to secure appointments. 

• Achieve and exceed daily, weekly, and monthly appointment-setting quotas. 

• Utilize CRM software to manage leads, track activity, and update appointment schedules. 

• Collaborate with the sales team to provide valuable insights on prospect needs and preferences. 

• Continuously improve appointment setting techniques and strategies. 

• Consistently hit FTA quota every month  

• Quota is 3 qualified FTAs set per week, 12 per month 

What we value 

• 2+ years of experience in cold call appointment setting in the tech industry 

• Strong preference for MSP industry appointment setting experience 

• Tangible examples of cold prospecting training history 

• Record of consistently achieving quota in prior appointment setting role 

• Strong phone presence and excellent communication skills 

• Ability to handle rejection and maintain a positive attitude 

• Innate challenger personality, Familiarity with The Challenger Sale is a plus 

• Proficiency in CRM software and sales tools 

• Strong organizational and time management skills 

• Motivated to achieve maximum impact 

Requirements

• Ability to work from home with some office time as needed  

• Occasional networking and evening or weekend work events (networking, community service, event sponsorships) 

• Consistent internet connection with a mobile backup/hotspot 

• Full time, hybrid 

Benefits

Salary 

The estimated-On Target Earnings range for this position is estimated to be $60,000 - $90,000/year.  Compensation will include a salary and a variable, uncapped commission structure.  Total compensation for this position may also include Employee Stock units, quarterly bonuses and other potential future incentives. Further note that total compensation for this position will be determined by each individual’s relevant qualifications, work experience, skills, and other factors.  

Benefits 

• Employee Stock Ownership 

• Employees (and their dependents) may enroll in medical, dental, vision insurance 

• Take what you need time off, not accrual based 

• 10 paid holidays throughout the calendar year 

• Employees can enroll in WEBIT’s 401k program