Investera Holdings is a Michigan family-operated company that buys established commercial cleaning and janitorial businesses in Chicago and keeps them running. We are operators and buyers, not brokers and not a passive fund. When we acquire a company, we install strong systems and a professional management layer so the business no longer depends on the founder being on-site every night. Our own portfolio, including CT Cleaners and Optimal Facility Services, is proof that we know how to run janitorial operations, not just finance them. If you have spent years building nightly routes through Chicago’s office towers, medical buildings, and industrial spaces, we want to protect what you built, keep your crews employed, and give you a clean, confidential way to step back on your terms.
Why Chicago owners are thinking about selling now
Chicago runs on square footage that has to be cleaned every single night. The Loop, West Loop, Fulton Market, and River North hold millions of square feet of Class A and Class B office space, and the return-to-office push has landlords competing on how clean and well-kept their buildings feel. Add the Illinois Medical District, the campuses at the University of Chicago and Northwestern, McCormick Place, O’Hare and Midway, and the endless brick warehouses along the Clearing and Bedford Park industrial corridors, and you have a market where recurring janitorial contracts are genuinely sticky. Property managers do not want to re-bid a reliable vendor; they want the same crews showing up, badged and trained, week after week.
At the same time, a large share of Chicago’s cleaning companies were built by owner-operators who are now in their late 50s, 60s, and beyond, and who have been carrying scheduling, payroll, and 2 a.m. call-outs on their own shoulders for decades. Labor is tight, insurance and workers’ comp keep climbing, and many owners simply have no successor. That is exactly the moment we are built for. Rather than let a lifetime of contracts get chopped up by a broker or absorbed by a national roll-up that guts the crew, you can hand the business to operators who will keep the name, the accounts, and the people intact.
Who we buy in the Chicago area
We are looking for a specific kind of Chicago janitorial or commercial cleaning company, not a fixer-upper and not a startup. The strongest fits look a lot like this:
- Recurring, contract-based revenue with signed nightly or scheduled janitorial accounts
- Around $500K or more in annual revenue or owner earnings (SDE) — close counts
- A capable crew of cleaners and at least one supervisor who can run routes
- A solid local reputation with property managers and long-tenured clients
- An owner who is open to a clean handoff or staying on for a transition
If you check most of these boxes, the conversation is worth having even if you are only starting to think about it. We would rather build a relationship a year before you sell than meet you the week you are burned out.
What makes selling to Investera different
No broker fees, ever. We buy directly, so you are not paying a five or six percent commission out of your own proceeds, and you are not being shopped around a marketplace to the highest bidder who may never actually close.
A confidential process from the first call. Your crews, your clients, and your competitors hear nothing unless and until you decide they should. Early conversations happen quietly, and we sign an NDA before you share a single account list.
Creative, flexible deal structures. Whether you want a clean full exit, a partial sale, a seller note, or an earnout tied to keeping accounts, we can shape the deal around your goals and your tax picture rather than forcing one template.
Operators, not a fund. A family that actually runs cleaning companies is buying yours, not a spreadsheet-driven investment vehicle that will strip overhead and flip it in three years.
How the process works
Our process is deliberately simple and low-pressure. It starts with a confidential phone call to understand your business, your accounts, and what you want out of a transition. If there is a fit, we sign an NDA and review basic financials and a contract list. From there we make a straightforward offer, and if you like it, we move into a short diligence and closing period. Throughout, you talk to the family that will own the business, not an analyst you will never see again. Most owners are surprised by how few people, and how little disruption, are involved.
We will take care of what you built
When we take over a Chicago cleaning company, the goal is continuity, not upheaval. We keep the crews, honor the routes, and stand behind the reputation you built with property managers across Cook County. What changes is the back office: we bring dispatching, quality-control walkthroughs, hiring systems, and a dedicated general manager so the operation runs without a single person holding it all together in their head. That is how your name keeps its standing after you step away, and how your best people get a more stable place to work.
Learn more about what we buy, see how we acquire commercial cleaning / janitorial businesses, or read about Investera Holdings.
Frequently asked questions
How much is my commercial cleaning business worth in Chicago?
Most established janitorial companies trade in a range of roughly 2.5 to 4 times SDE (seller’s discretionary earnings). Recurring contract revenue, crew tenure, client concentration, and margins move you within that band. This is a typical range, not a guarantee — we give you a real number after a confidential look at your financials.
Will you keep this confidential?
Yes. Confidentiality is the default, not an add-on. We sign an NDA before reviewing any client or financial detail, and nothing reaches your crews, accounts, or competitors until you choose to tell them.
Do I have to pay any broker or commission fees?
No. We are the buyer, not a broker. There is no listing commission and no success fee taken out of your proceeds — the number we agree on is the number that governs the deal.
Can I stay involved after the sale?
You can, and many owners do for a while. Some stay on for a short transition to introduce clients and crews; others consult part-time. If you would rather walk away cleanly, we can build the deal around that too.
How long does the whole process take?
A typical deal moves from first conversation to close in about 60 to 90 days, depending on how organized your records are. We can move faster or slower to fit your timeline.
What areas around Chicago do you buy in?
We buy throughout Chicago and the surrounding Cook County suburbs, including Evanston, Oak Park, Cicero, Skokie, and Berwyn. If your routes run across the metro, that is a plus, not a problem.
Start a confidential conversation
If you own a commercial cleaning or janitorial business in the Chicago area and have even started to wonder what stepping back could look like, let’s talk. A first conversation is completely confidential and carries no obligation — just a straight discussion between you and the family that would own and run your company next. Reach out to Investera Holdings and we will listen before we ever talk numbers.