She Took Over A 37-Year-Old Roofing Company And Rebuilt It From Scratch w/ Sasha Wilde

Most people buying a home service business picture the same sequence: buy it, hire a general manager, go buy the next one. Sasha Wilde tried that in year two and it cost her nine months and real money.

Wilde owns Sexton Roofing & Siding in West Hatfield, Massachusetts. She spent about a decade as a project manager, including large-scale pharmaceutical construction work, got an MBA, and grew tired of working for someone else. In 2023 she and her husband Tim moved from New Hampshire to buy the company from founder Everett Sexton, who had run it for close to four decades. Three years in, the team is 10 people plus a subcontracting crew, and the company has expanded from roofing into siding, windows, and doors.

What makes her worth listening to is how plainly she accounts for the mistakes. This post covers what her diligence missed, the hiring order she would redo, and what she did to get the phone ringing.

The supply side of this market is not tight. Over half of US small business owners are now over 55, and in 2022 roughly 510,000 small and mid-size businesses exited: 92% of them by closing, and only 5% by selling. Gallup found that 43% of employer-business owners plan to sell eventually, rising to 74% among those nearing retirement.

So the business Wilde describes, a well-regarded operator ready to retire, is not rare. What is rare is someone showing up to buy it.

Her own path there was not direct. The switch flipped when one of her husband’s best friends acquired a business and the two of them realized that was an option.

From there she ruled things out fast. A Chinese restaurant died when their son threw up on the table during a visit and the staff brought one paper towel. Daycares went next, because she could not see herself charging families enough to run one profitably. Home services won, and she kept the search in New England because that is where their family is.

She is candid that she went in with “a lot of unearned confidence at that time,” and naive about how hard the transition would be.

The mechanical lesson is worth copying. She set a six-month horizon and built a simple Excel model that took a seller’s numbers and returned her loan payment, her return, and what the figures looked like with her own changes. Before her first letter of intent, that model plus Google reviews and the website was the whole analysis. Her view is that the first LOI is usually not the business you buy, and if you never issue one, you may never do a deal at all.

Nothing in the formal process told her to walk away. Two things she did not nail down cost her anyway, and both are fixable in an afternoon of paperwork.

The first was warranty exposure. Her lawyer wanted an addendum in the contract specifically addressing warranty claims. She took the seller at his word that claims were rare or minimal, and skipped it. She now knows that was not accurate, and her position is unambiguous: she would insist on that addendum in the future even if it killed the deal.

The second was the handoff itself. A seller is supposed to run the business normally through closing, and this one did not. She inherited roughly 12 signed contracts, which in roofing terms is about 12 to 15 days of work. She bought a company with effectively no backlog and had never sold a roof in her life.

A rainy June and July gave her cover. The crews could not tell there was no work lined up, because there was no weather to work in either.

Then there is the question she wishes she had asked, and it has nothing to do with financials. “One of the things I wish I had talked to my seller about early on is what does your life look like? How many hours do you spend in the business?”

She only learned close to closing, after they had already moved and given up their careers, that the seller worked seven days a week. She and Tim now work weekdays, which she counts as a real gain, but it was not something she had priced in.

The deal also nearly died at the table. A week before closing, the seller struggled with an online signature, got into a shouting match with the bank and with her, and threatened to walk.

Her first two hires were the right calls, made in a panic.

A salesperson came on within about a week, because the pipeline was nearly empty and nobody at the company knew how to sell roofing. Then a business manager, hired partly because Wilde was four months pregnant at closing and would be on maternity leave in October. That hire took over the phones, cleaned up the bookkeeping, and got subcontractor paperwork current.

On the timing, she is direct: “I’m not sure I would advise anyone who is actively pregnant to acquire a business that year.” Her husband took four days off when the baby came. She took about a week.

The expensive hire came in March of 2024. She brought in a general manager, expecting him to run everything so she could start thinking about the next acquisition, which has always been the goal. She was handing the business to someone she did not really know, and over the following nine months it became clear it was not working. They fired him inside the same year.

The hire that actually freed her up arrived that fall, and she was not looking for it. A production manager landed in her lap, took over the day-to-day execution she had been carrying, and became the first moment a real weight came off her shoulders. In her words, she did not know she needed one and did not know he was the next unlock for the business. Hiring him is also what made firing the general manager possible.

Her stated lesson is the most portable thing in the episode: “I tried to hire too high level of a role too quickly before I had really defined what I want that role to do and accomplish.”

The distinction she draws between the two roles is worth keeping. A general manager is responsible for everything an owner oversees: sales, production, marketing, admin, financials. A production manager owns one thing, which is whether projects get executed well and profitably. “He is execution, whereas GM is oversight.”

Given the choice again, she would skip the general manager that year and go straight to production, because that is what freed her time to figure out the next thing. She is now looking at maybe 2028 for a general manager, when the business has a few more million in revenue and can support the experience level she would want.

The second half of the lesson is pacing. She was not patient enough to wait for the right person, and she has had further mishires since. What has improved is not her hit rate but her reaction time: she is faster now at identifying a bad hire and acting on it.

A senior hire does not substitute for a defined role. Define the job, then find the person, in that order.

Wilde does not hire for the role in front of her. She hires for whether someone will outgrow it.

“I would hire that Swiss Army knife person with no experience every day of the week.” In her interviews she walks candidates through her core values and then asks about theirs, looking specifically for people who want to grow into something.

The mechanism she stumbled into is a single entry-level seat. Her client care rep role attracts a lot of applicants, which means she sees a lot of people, and it has become her intake point for the whole company. The first one moved into sales and now runs a dual repair technician and sales role. The second is learning production, so next year she plans to hire a third and move that person into production, which lets the production manager take on more.

The side effect is coverage. When the production manager takes a rare vacation, the client care rep fills in, and Wilde says she does not pick up much extra work when someone is out.

That is what makes her schedule survivable. With three kids under six, she sometimes gets four working hours in a day, and the business runs because the team does not need her in it.

Asked how she got the phone ringing, her first answer was that she is still figuring it out. The honest version is that it was a dozen things at once, not one channel.

Brand came first. In 2024 she moved from a small sign on the pickup door to a full truck wrap in green, gray, and purple, deliberately not the black or red that every other roofer in the market uses. They clarified what the brand stood for without changing the name.

Then the digital foundation. They rebuilt the website, rewrote every page for search down to image metadata, and began running Google Ads with what she calls real money rather than a couple of grand here and there.

The rest is relationship work, and it is the part most operators underinvest in. Chambers and local networking, yard signs, teaching her team to door knock, and referral partnerships with builders, realtors, property managers, solar companies, and most recently an insulation contractor.

Repairs matter too. A ridge cap that buys a homeowner five more years is both the right call and a replacement lead later.

Her channel mix is still catching up to her ambitions. Marketing will land at roughly 2% of revenue this year, which she acknowledges is low for the growth she wants, and her first draft of next year’s budget puts it at 3.6%.

Two things are queued for the slow months. She is testing an app that gives customers live visibility into where their project sits, from approval through permitting, with a formal referral program attached. And because Massachusetts winters stop most roofing work, they are lining up window installations to fill the gap.

Related: TradeOps plans and pricing.