Sales Development Representative
Job Overview
Were looking for a driven, disciplined, and highly coachable Sales Development Representative (SDR) to help us expand our IT Managed Services client base. In this role, you will be responsible for generating pipeline through proactive outbound outreach—identifying prospects, initiating conversations, qualifying opportunities, and scheduling high‑quality sales meetings for our team.
This position includes both remote outbound calling/emailing and in‑person canvassing in targeted local markets. You must be comfortable visiting prospective businesses and engaging decision-makers face‑to‑face.
Key Responsibilities
Outbound Prospecting & Lead Generation
- Make high‑volume outbound cold calls and emails to targeted prospects
- Conduct in‑person canvassing and door‑to‑door prospecting to businesses within our Ideal Client Profile (ICP)
- Prospect across phone, email, LinkedIn, and field canvassing to build a strong pipeline
- Identify new business opportunities within the Greater Chicago metropolitan area, specifically Kankakee, Will, Iroquois, and Cook Counties
Discovery & Qualification
- Engage CEOs, COOs, Directors of IT, and other key decision-makers
- Identify prospect pain points related to cybersecurity, IT support, and infrastructure
- Confirm alignment with our Ideal Client Profile before handing off to sales
Appointment Setting
- Secure high‑quality meetings and demos for the sales team
- Ensure meetings include proper context, expectations, and key stakeholders
- Manage follow‑ups to reduce no‑shows and maintain pipeline momentum
Process, Tools & Reporting
- Log all activity—phone, email, and field canvassing—in the CRM
- Maintain accurate records of conversations, lead stages, and outcomes
- Follow structured outreach sequences and contribute feedback to improve them
Collaboration & Training
- Work closely with the sales and marketing team to refine messaging
- Participate in regular sales training, coaching sessions, and skill‑building
- Help strengthen prospecting strategies based on field and phone feedback
Qualifications
- Proven experience in outbound calling, appointment setting, or BDR/SDR work
- Door‑to‑door or face‑to‑face sales experience is a major plus
- Comfortable with regular in‑person canvassing in the Chicago metro area
- Strong communication, listening, and interpersonal skills
- Coachable, accountable, and motivated to grow professionally
- Familiarity with IT services, MSPs, or cybersecurity is beneficial but not required
- Must be organized, detail‑oriented, and comfortable using CRMs
Success Traits
- Self‑motivated and disciplined
- Comfortable initiating conversations both over the phone and in person
- Resilient when handling objections and rejection
- Process‑driven with strong follow‑through
- Confident speaking with business owners and executives
Benefits
- Bonus/Commission Plan
- Retirement plan (IRA)
- Health, dental, and vision insurance
- Paid time off
- Supportive team environment
- Ongoing training, mentorship, and advancement opportunities
Sound like you? Apply now and lets connect.
