Full-Cycle B2B SDR - Managed IT Services (Lake County/Chicagoland)

We're a growing managed IT services company looking for an experienced full-cycle SDR to independently source, research, and book qualified meetings with SMB prospects. You will build your own prospect lists from our ICP rather than working off supplied leads. You'll own the full cycle: identify decision-makers, verify contacts, research companies, personalize outreach, follow up, qualify interest, and book meetings directly on our calendar. You're welcome to use your own proven messaging approach and cadence, we're not looking to hand you a rigid script, though we'll review and approve overall positioning and your first 3-5 outreach messages before broader sending begins. Target ICP: 5-75 employee SMBs, professional offices, nonprofits, churches, veterinary/medical-adjacent businesses, accounting/financial firms, and similar organizations in Lake County and northern Chicagoland. This is a paid pilot engagement (30-day initial window) targeting roughly 25-50 genuinely qualified, well-researched prospects, quality over raw volume. A meeting only counts as qualified if the prospect fits our target profile and understands why they're meeting with us. Strong performers will move into an ongoing bench relationship with more consistent campaign work. You'll track prospects, decision-makers, contact info, outreach attempts, responses, and meetings in a tracker we provide, separate from our main sales pipeline during the pilot. Compensation: Commission-based, no hourly pay. - $40-50 per qualified meeting held (meeting must actually occur, not just be booked) - 10% of the client's first-month recurring revenue on any closed deal, no cap, scales with deal size - Close bonus paid within 15 business days of the client's first invoice payment clearing, communicated clearly upfront Guardrails: relationship-first approach, no misleading claims, no unauthorized pricing commitments, no technical promises without approval, no disparaging other IT providers, no pretending to be Jahmar, no mass-spam tactics. All prospect research, contact data, and campaign results created for this engagement are our work product and may not be reused for other clients. Please answer in your proposal: 1. Walk me through exactly what you'd do in your first two weeks if given an ICP but no prospect list. 2. What parts of your current prospecting process would you not want us to change, because you already know they work? 3. What results have you produced specifically for MSPs, IT companies, or other B2B technology providers? 4. How do you handle outbound email infrastructure and domain reputation for a client like us? Do you expect us to provide an inbox/domain, or do you bring your own outbound setup? 5. What would you need from us before you could start prospecting? Prior MSP/IT services, cybersecurity, telecom, or B2B SaaS prospecting experience strongly preferred.