Inside Sales Representative
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.
Salary
$100,000 - $130,000 On Target Earnings
Top Skills
What We Do
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.
Why Work With Us
Rejigg is a venture-backed company with big ambitions.
