ABOUT THIS ROLE
Most internships in finance and consulting run on apprenticeship. You spend the first year or two on grunt work before you touch anything that actually moves revenue.
This one is built the opposite way. The grunt work is already automated. We use Claude and other AI tools to handle list-building, data pulls, research, and first drafts, which means your time goes to the parts that need judgment: talking to a customer, reading a number, deciding what to do next.
Leaders Roofing is an independent, family-owned roofing company in Chicago’s northwest suburbs. Thirty years in, second generation, and building the operations to grow. Home services is one of the most actively consolidated sectors in private equity right now, and platforms like Guild Garage Group and Chimney Collective are acquiring family-owned contractors at pace. We’re not one of them and don’t plan to be. But the discipline that makes those platforms valuable, meaning clean data, documented process, and real unit economics, makes an independent business stronger too. That’s the work you’d be doing.
You’d work directly with the owner, a Villanova alum who started his career in merchant banking, moved to private equity, spent time at a multi-strategy hedge fund, and now works at a family office. This is closer to a chief of staff role than a typical internship.
THE SHAPE OF IT
This is an operations role, but a small business doesn’t respect neat function boundaries and neither will this job. You’ll get real exposure to sales, marketing, analytics, and operations, often in the same week. That’s the point. Wherever you turn out to be strongest, we’ll push more of that work toward you.
Sales. Work inbound leads, respond fast, connect with homeowners, and stay with them through the quote and follow-up process. Chase open quotes on a real cadence, and find out why the ones we lost went elsewhere.
Marketing. Own the review engine and Google Business Profile, which largely decide whether a local business gets found at all. Learn how search is shifting from traditional SEO toward answer engine and generative engine optimization, and help us get ahead of it.
Analytics. Build the unit economics: customer acquisition cost and return by channel across paid search, lead-generation platforms, organic, and referral. Diagnose why quoted work converts or doesn’t, and what to change.
Operations. Design and run a reactivation campaign against a 500-plus job customer database, recover real dollars through vendor and lead-platform credit reconciliation, build AI-assisted workflows that eliminate manual work, and assemble the KPI reporting the owner runs the company from.
WHAT YOU’LL GET
- Direct mentorship from an owner with a private equity and investing background, one-on-one rather than through a program
- Work attached to revenue in your first month, not your second year
- Real customer-facing experience, not just analysis from behind a screen
- Genuine exposure to lower-middle-market unit economics and the M&A dynamics reshaping home services
- Hands-on practice deploying AI tools against real operational problems, a skill set employers are hiring for and few students have actually done
- Work that holds up in an interview
UPSIDE
The hourly rate is the floor, not the ceiling. Someone who proves themselves quickly will have the chance to share in the upside of what they help build, on top of the hourly rate.
WHO FITS
High achieving business, finance, economics, or analytics student who wants to understand how a business actually runs. Strong academic record, 3.5 or above preferred. Comfortable in spreadsheets, comfortable talking to customers, and genuinely interested in using AI tools rather than just talking about them. Self-directed. You’ll get projects, not a babysitter.
DETAILS
About 10 hours a week, fully remote, flexible around your class schedule. $25 an hour. Potential to continue across semesters and to grow the scope of the role.
