Chief Rebel: Sales Development Representative

Headquarters: Chief Rebel URL: https://thechiefrebel.com/ Sales Development Representative Job Description This role is about starting conversations with business owners and moving the right ones forward

You will call founders who are thinking about selling, qualify their situation, and book them into next-step conversations

You will also own follow-up

If someone books, you make sure they show up

This is outbound, phone-heavy work

You are dealing with busy owners who have heard plenty of pitches and do not have time for fluff

What you’ll do day to day Make a high volume of outbound calls to business owners Have clear, direct conversations to understand their business, timing, and intent Explain what exit planning and selling actually looks like in simple terms Book qualified founders into scheduled conversations Follow up every day with booked calls to confirm attendance and reduce no-shows Re-engage founders who go quiet but are still a potential fit Keep accurate notes so the team has full context Hit weekly activity and booking targets Who this role is for You are fully fluent in English with no accent You are confident on the phone and easy to understand You can keep control of a conversation without sounding pushy You are persistent with follow-up and don’t assume someone will just show up You handle rejection without getting sloppy or discouraged You are consistent, reliable, and organized Experience that helps 1–3 years in outbound sales, SDR, or inside sales Experience speaking directly with founders or decision-makers is a plus Comfortable learning financial and business concepts You do not need deal experience, but you must be sharp and coachable Work setup Fully remote Must work within Central Time business hours, plus or minus 4 hours Quiet work environment and strong internet required How success is measured Calls completed Qualified bookings Show rate on booked conversations Quality of notes and handoff Why this role matters You set the tone for every founder relationship

If you do this job well and conversations are clean, calendars stay full

OTE: $50-55K with base + performance bonuses To apply: https://weworkremotely.com/remote-jobs/chief-rebel-sales-development-representative