Why I Buy Cleaning Companies Instead of Software | Shawn Heeren, Crestline Cleaning Group

What we talked about.

In this episode of the Sunny Ray Show, host Sunny Ray talks with Shawn Heeren of Crestline Cleaning Group about leaving software sales to buy commercial cleaning companies. Shawn explains how a wave of baby boomer owners nearing retirement needs trustworthy buyers, and why he chose a thin-margin but recession resistant, highly fragmented industry. He describes reaching owners through accountants, referrals, and outbound calls, and how Crestline plans to keep local names, staff, and customers while unifying back-end systems and adding a sales and marketing engine. The conversation covers creative deal funding, including seller financing and rollover equity, and where AI can cut the cost of outreach for both sales and hiring. Shawn also discusses how robots could affect labor-heavy cleaning margins, shares that his search is about ten months in with heavy diligence ahead, and outlines a long-term goal of national expansion across Canada and possibly the United States.

A former software sales leader explains why he is buying boring, recession resistant cleaning companies from retiring owners instead of selling software.

The questions, and the answers.

What made you want to own businesses instead of selling for them?

I got into sales to make money, but business ownership always stood out to me. As a salesperson you might keep around 7% of a $1,000 ticket. As an owner, before taxes, labor, and tools, you keep the equity slice. That makes ownership a better wealth-building engine and better leverage than sales.

Why commercial cleaning, and what do most buyers walk past?

Margins are thinner, roughly 8% to 17.5%, which scares some people. But buildings always need cleaning, through COVID and recessions, so it is durable and consistent. It is less exposed to AI disruption, and it is hyperfragmented, with thousands of companies across Canada, so there is plenty of volume to buy from.

Why does trust matter so much when buying from retiring owners?

Many owners distrust massive companies buying theirs and do not want to be just another name on a list. They want their people, customers, and legacy looked after. Not every buyer can afford a business either, so choosing the right buyer matters, and trust is the name of the game.

How do accountants fit into how you find deals?

Accountants see an owner's financials every month and quarter, so they often sense a sale is coming before the owner does. They will not share client details. I explain what we do, ask them to call us first when a client nears that point, and stay top of mind with regular follow-ups.

What do you buy, keep, and change at Crestline?

We buy commercial cleaning businesses only. We keep the name, staff, and customer base. We change the back end, unifying financial systems, CRM, and reporting so it is one company with several regional faces. We also add a go-to-market sales and marketing motion, since these service companies are usually weak at sales.

How do you fund an acquisition strategy like this?

It is not just equity plus a bank loan. Seller financing lets the seller act as the bank, say 30% of the price repaid with interest over three years. Rollover equity lets a seller keep, for example, 20% while I buy 80%, so I need less cash upfront and keep control.

Where does technology help a cleaning company today?

Basics like reporting, financial systems, and CRMs have existed for years. The bigger underused opportunity is AI for outreach. It makes finding leads and recruits, qualifying them, and contacting them far cheaper. Hiring is a form of sales, so the same tools help win contracts and find cleaners.

What does the next 90 days look like, and where is Crestline headed?

The next 90 days are heavy on diligence, with financial and legal reviews, NDAs, and early conversations. Searches take six to 36 months to a first close, and we are about month 10. We are here for a decade plus, aiming for national expansion across Canada and possibly the United States.