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