Sales Development Representative

Chicago based managed IT services and Dynamics 365 partner. We help small and mid sized businesses run modern, secure, well supported technology environments. We are growing our pipeline and need a hunter who lives on the phone and knows how to turn strong lead data into booked meetings. ## The Role This is a phone first outbound role. You will spend your day dialing small business owners and decision makers, opening conversations, and qualifying real opportunities for our sales team. We invest in clean, well researched lead lists, so your job is to work that data hard and convert volume into conversations. If you measure your success in connects, conversations, and meetings booked, you will do well here. ## What You Will Do - Run high volume outbound calling campaigns against curated small business lead lists - Open cold conversations with owners, operators, and IT decision makers and quickly establish relevance - Qualify prospects against our target profile and hand off sales ready meetings to account executives - Keep CRM records clean and current with accurate dispositions, notes, and next steps - Hit and exceed daily and weekly activity and meeting targets - Test and refine talk tracks, objection handling, and call timing to improve connect and conversion rates - Partner with sales and marketing to sharpen targeting and feed back what you learn from the field ## What We Are Looking For - One or more years of outbound sales, SDR, BDR, or cold calling experience, ideally in B2B - A genuine appetite for the phone and a high tolerance for volume, with the discipline to keep dialing - Strong verbal communication and the ability to think on your feet through objections - Comfort working from lead data and a habit of keeping the CRM accurate - A track record of hitting activity and meeting based goals - Self motivation and resilience, with a coachable, improvement minded attitude ## Nice to Have - Familiarity with Trellus or a similar AI parallel dialer, since speed and call volume matter in this role - Experience selling into small businesses or in managed IT, technology, or professional services - Comfort with modern sales tooling such as Apollo, Notion, Claude, or similar CRM and sales automation platforms ## Why Join Us You will work strong lead data instead of cold guessing, with the dialing technology and coaching to make every hour on the phone count. This is a high activity, high visibility role with a clear path into a full cycle sales seat for the right performer.