Sales Development Representative

Posted 8 hours ago

Company Description

Chief Rebel helps business owners understand what their business is actually worth and what to do next.

Most founders don’t have clean numbers, clear options, or a real plan for an exit. They’re busy running the business, making decisions in the dark, and reacting instead of preparing. We exist to change that.

We work with owner-led businesses to bring clarity to valuation, readiness, and timing. Sometimes that means preparing for a sale. Sometimes it means fixing what would break a sale. Sometimes it means building a business worth keeping. We don’t push outcomes. We surface reality and help founders act on it.

We are not a brokerage or a coaching program.
We are a technology company focused on execution and precision.

Our work sits at the intersection of operations, finance, and real-world decision-making. The people who do well here are disciplined, direct, and comfortable talking to founders who don’t have time for fluff.

If you care about doing work that actually moves businesses forward and you take ownership seriously, you’ll fit in.

Apply now

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