Strategy & Operations Summer Intern at Rejigg in Chicago, IL

About Us: Rejigg help small business owners sell their companies by connecting them with qualified buyers. We're building a more transparent, founder-friendly marketplace for business acquisitions — and we're scaling quickly.

This summer, we're bringing on a Strategy & Operations Intern to work as a hands-on generalist across the business. This is not a narrow, task-list internship: you'll work on real projects that matter. We're looking for a curious, motivated self-starter who wants to see what it's like to work at a fast-growing, VC-backed startup from the inside.

Think of it as a crash course in what it actually takes to build and run a company

What you'll do
Your work will shift based on what the business needs, which is part of what makes this role interesting. Some weeks you might be deep in research; others you'll be helping prep for a leadership meeting or pulling data to answer a quick question.

Examples of what you might own or support:

• Support monthly goal setting & retros. Work closely with leadership to prepare agendas, gather inputs, organize docs, and track follow ups

• Assist with one-off analyses. Help the leadership team examine emerging trends on the platform. Put together simple slides or summaries that explain complex topics clearly

• Support customer & user research. Help set up user interviews with buyers, sellers, or partners. Synthesize themes and insights into clear notes or short summaries

• Work closely with sales. Partner with the sales team and founders on day-to-day execution: maintaining pipeline hygiene, updating CRM data, pulling sales reports, and supporting follow-up cadences

• General operations support. Help tidy up workflows, documentation, and lightweight processes so the team can move faster

• Special projects. Work side-by-side with leadership on short-term initiatives as they emerge — new partnerships, experiments, product or ops tweaks. Take ambiguous ideas and help break them into clear, actionable tasks

What we're looking for

• Currently enrolled as a rising junior (completing sophomore year this spring)

• Based in Chicago for the summer, or able to be — you'll work in-person with the team at our River North office

• Comfortable with ambiguity. You're okay when priorities shift and you have to jump between different types of work

• Organized and detail-oriented. You follow through on things without needing a lot of hand-holding, and you keep track of the details

• Clear communicator. You can write a clean email, summarize a conversation, and ask good questions

• Genuinely curious. You ask "why" and want to understand how things work

Nice to have

• Coursework or interest in business, economics, entrepreneurship, or a related field

• Involvement in a consulting club, investment club, or entrepreneurship organization on campus

• Any prior exposure to startups, small businesses, or sales — even through a class project, internship, or job

What success looks like by the end of the summer

• You've owned at least one project from start to finish and can speak to what you built and why it mattered

• The leadership team trusts you to run things down independently and bring back clear, organized outputs

• You've built a real understanding of how Rejigg works — the business model, the customers, the team — and can speak to it confidently

• You leave with a strong sense what it looks like to work at an early-stage startup, and have a network of people rooting for you