From Family Business to Acquisition: How West Orange Roofing Got Sold

If you are ready to sell your roofing company, this episode shows you exactly what that process looks like from the seller’s side. West Orange Roofing started in a garage in Winter Garden, Florida. Bobby Swindle’s father founded it in 1978. Bobby got his license in 2014 and built it into a real company. Then he and his wife Kendra sold it to Dunes Point Capital. In this episode of Roofing Contractor’s Best of Success, Art Eisner sits down with Kendra and Claudio Vilas to walk through what the process looked like from the seller’s side — the paperwork, the pressure, and why they could not have made it through without the right team.

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  The accounting and bookkeeping will be the hardest part — and most owners are not ready for it. Buyers ask questions that have nothing to do with how well you run your roofs. They want to see your numbers organized, reconciled, and explainable. If that is not in order before you go to market, the process will be painful and the price will suffer.
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  You cannot do this alone. Kendra said it directly: without Claudio and the team he brought in, they would not have made it through. This is not a process you hand to your regular accountant or your family attorney. You need people who have done this before, specifically in M&A.
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  Brand legacy and market position are real assets in a sale. West Orange Roofing had referrals coming in from roofs Bobby’s father installed in the 1990s. That kind of embedded reputation in a local market is something buyers notice and pay for.
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  Getting the business ready before going to market changes the outcome. Claudio worked with the Swindles to prepare the financials and organize documentation before any buyer saw the company. That preparation is what gives you leverage and speeds up the close.
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  Selling is part negotiation, part finance, part psychology. Buyers ask a lot of questions that feel personal and disorienting if you are not prepared for them. Part of Claudio’s job is managing expectations so sellers do not make emotional decisions in the middle of the process.
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  Your regular accountant and your regular attorney are not the right people for this. The accountant who does your taxes is not the same as someone who prepares a quality of earnings report. The attorney who handles your contracts is not the same as one experienced in M&A. The right team for your business is not the right team for your sale.
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  Roofing is fertile ground for sellers right now. Private equity is actively looking for roofing companies. Claudio chose to focus exclusively on this industry because the money is here, the buyers are serious, and owners who built from nothing deserve to get the most out of what they created.

People who built their companies from scratch and now have something strong — they deserve to get as much money as possible for what they did with their life.

Claudio Vilas, CMSBB, CBI, CMAP

Bobby Swindle’s father started West Orange Roofing in 1978 in Winter Garden, Florida. Bobby grew up on roofs. He and his brother Billy were working alongside their father as teenagers. When their dad passed in 2009, Bobby eventually got his license in 2014 and built the company back up from a garage operation into a full residential roofing business covering all of Central Florida, with 30 to 35 employees and a name that had been in the community for decades.

Kendra came into the business when Bobby got his license and helped build it alongside him. By the time they started thinking about selling, West Orange had strong production, a loyal referral base going back to the 1990s, and a reputation that made them a real asset in the eyes of a buyer. That is not something you can manufacture quickly. It takes years of consistent work in a community, and buyers know the difference.

The decision to sell came together around November. They had friends who had sold a roofing company, heard about the process, and then sat down with Claudio. From that first conversation, things moved forward. What followed was a process that Kendra described as a lot of accounting and paperwork — organized, tracked, and managed with Claudio’s help and a team he brought in to support the financial preparation.

Claudio was direct about what made West Orange strong as an acquisition target. The production was excellent. The team knew the business. The market position was real. But like most owner-operated companies, the accounting side needed work before buyers could evaluate it properly. That is not a criticism — it is the reality for nearly every roofing company that comes to market. Owners are focused on running roofs, not preparing quality of earnings reports. The job before going to market is closing that gap.

Kendra was clear on one point above everything else: they would not have made it through without Claudio and the team he assembled. That includes the M&A-experienced accountants and attorneys who handled the technical side of the transaction. Your regular accountant and your regular attorney are not built for this. The people who prepare your taxes are not the same as the people who prepare a quality of earnings report that holds up under PE scrutiny. Getting the wrong professionals in the room can cost you the deal or cost you points off the price.

Claudio also explained why he chose to focus exclusively on roofing. After years as a business broker across multiple industries, he saw an opportunity where buyers are serious, money is actively flowing in, and sellers are often unprepared. By focusing on one industry, he gets to know the buyers, understand what they are looking for, and position his clients accordingly. That focus is a direct benefit to the seller.

The outcome for the Swindles was a sale to Dunes Point Capital. Bobby is staying on to help the business grow under new ownership. Kendra is stepping back — doing the things she always wanted to do. That is the exit working the way it is supposed to. Not a forced departure. Not a fire sale. A planned transition that respected what they built and gave them options on the other side.

If you have a roofing company that has been in your family for years, or one you built from scratch, and you are starting to think about what comes next, this episode is worth your time. The process is not simple. But with the right team and the right preparation, it works.

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