Inside Sales Representative

Inside Sales Representative

Location: Chicago, IL (in-person, Mon-Fri in our River North office)

Type: Full-time

Target start date: December 7, 2026

Rejigg is a fast-growing platform helping small business owners exit their companies by connecting them with qualified buyers. We’re building a better, more transparent marketplace for business acquisitions — and we’re looking for driven, resourceful sales professionals to help bring more businesses onto the platform.

We’re hiring an Inside Sales Representative to join our high-performance sales team. This is a full-cycle, outbound-heavy role based in our Chicago office. You’ll be responsible for sourcing and onboarding small business owners who are exploring a sale — from the first cold call to getting their business listed and ready to attract buyers.

This role requires high activity, a sharp learning curve, and a genuine curiosity about small businesses. If you’re excited by the idea of calling 100+ business owners a day and helping them take a major step toward retirement or a new chapter, we want to hear from you.

What You’ll Do

Own the full sales cycle: prospect, qualify, and close new business listings on the Rejigg platform

Make hundreds outbound calls per week to small business owners (retiring baby boomers, family business operators, etc.)

Conduct thoughtful conversations to educate business owners on the process of selling and the benefits of Rejigg

Guide sellers through onboarding and listing, answering questions and ensuring a smooth experience

Maintain accurate and detailed records of all outreach, calls, and follow-ups in our CRM

Hit monthly sales targets

What You’ll Learn

How small business sales work — including concepts like EBITDA, SDE, deal structures, and buyer motivations

How to communicate effectively with skeptical, time-strapped business owners

How to adapt your pitch and approach to different industries, owner personalities, and deal sizes

We don’t expect you to come in as an expert — but we do expect you to learn fast, stay curious, and ask great questions.

Who You Are

You’re hungry, competitive, and thrive on hitting goals–you’re a hunter.

You’ve made hundreds (or thousands) of cold calls and still get excited by the chase

You’re resilient and know how to handle rejection without losing your spark

You’re comfortable learning new terminology and operating in a detail-oriented environment

You care about helping people make one of the biggest decisions of their lives

Qualifications

1–3 years of sales experience (especially startup, inside sales, or call-heavy roles) preferred, but new graduates welcome to apply

Excellent verbal communication skills — you can earn trust quickly over the phone

Strong organizational skills and ability to prioritize in a fast-paced environment

Proficiency with CRM and sales tools (e.g. HubSpot)

Bachelor’s degree or equivalent work experience

If you’re looking for a place where your hustle directly impacts the company’s growth — and where you’ll learn a lot about sales, business, and entrepreneurship — Rejigg is the place for you.

Salary

$55,000 Base Salary

$105,000 On Target Earnings (uncapped commission program)