Sales Development Representative

Culture Fits•Bradley, IL

19h•Hybrid

About The Position

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.

Requirements

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
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

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