M&A Sourcing Analyst

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

Type: Full-time

Target start date: Early April 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, analytical people to help bring more businesses onto the platform.

We’re hiring an M&A Sourcing Analyst to help originate and onboard small businesses that are potential candidates for a sale. This is a front-line, outbound-heavy role where you’ll spend your days identifying attractive businesses, talking with owners, and collecting the information we need to evaluate fit and bring them onto the Rejigg platform.

You’ll be combining high-activity outreach (calls, email, sequences) with structured discovery and light financial analysis. If you’re excited by the idea of speaking with 100+ business owners a day, digging into how their companies work, 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 sourcing cycle: prospect, qualify, and bring new business listings onto the Rejigg platform

• Remain partners to business owners throughout the process: remain a trusted advisor to owners as they go through the sale process

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

• Conduct thoughtful, structured conversations to understand each business’s revenue, profitability, customer mix, and owner goals

• Collect and organize basic financial and operating data (e.g., revenue trends, margins, EBITDA/SDE inputs) to help determine fit for our buyers

• Summarize each opportunity clearly in our systems so internal teams and buyers can quickly understand the deal

• Guide sellers through onboarding and listing, answering questions and ensuring a smooth, accurate, and complete information-gathering process

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

• Hit monthly sourcing and listing targets

What You’ll Learn

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

• How professional acquirers (search funds, independent buyers, private equity groups) evaluate deals and what they look for in a business

• How to communicate effectively with skeptical, time-strapped business owners about one of the biggest financial decisions of their lives

• How to adapt your approach to different industries, business models, owner personalities, and deal sizes

• How to use data, activity metrics, and feedback to continuously refine your outreach and sourcing strategy

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 energized by the chase.

You’re curious and analytical — you like understanding how businesses make money and what makes one more attractive than another.

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, data-driven environment.

You care about helping people make one of the biggest decisions of their lives and want to build real experience in M&A / small business finance.

Qualifications

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

• Comfort talking about basic financial concepts (revenue, profit, margins) and interest in learning more about M&A

• Outbound sales prospecting or deal sourcing experience, or a clearly demonstrated interest in developing those skills

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

• 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 deal sourcing, small business finance, and entrepreneurship — Rejigg is the place for you.

Salary

$55,000 Base Salary

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