Inside Sales Representative

Rejigg; Chicago (IL); Hybrid; USD 105,000 - 130,000; Full time

Job summary

A growing business acquisition platform in Chicago is seeking an Inside Sales Representative to join their sales team. This full-cycle, outbound-heavy role involves making hundreds of calls to small business owners looking to sell. Ideal candidates are competitive, resilient, and have a passion for helping others. Preferred qualifications include 1–3 years of sales experience and proficiency with CRM tools. Compensation ranges from $105,000 to $130,000 in on-target earnings, with a hybrid work model.

Qualifications

• 1–3 years of sales experience preferred, but new graduates welcome.
• Excellent verbal communication skills to earn trust quickly over the phone.
• Strong organizational skills and ability to prioritize in fast-paced environment.

Responsibilities

• Own the full sales cycle: prospect, qualify, and close new business listings.
• Make hundreds outbound calls per week to small business owners.
• Guide sellers through onboarding and listing, answering questions.

Skills

Sales experience

Verbal communication skills

Organizational skills

Proficiency with CRM

Education

Bachelor's degree or equivalent work experience

Tools

HubSpot

Job description

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Location: Chicago, IL (hybrid, Mon-Thu in our River North office)

Type: Full-time

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.

$105,000 - $130,000 On Target Earnings

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