Sales Development Representative
Chief Rebel

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