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He was a corporate consultant. She had an MBA. Neither had roofed a day in their lives — then they bought a roofing company and doubled it.
Tim Wilde and his wife Sasha bought Sexton Roofing & Siding in Western Massachusetts in 2023 — a 40-year-old brand the previous owner ran solo at about $2 million a year, working 16-hour days, seven days a week. Neither of them had ever roofed: Tim came out of corporate pharmaceutical-construction consulting, and Sasha has an MBA and always wanted to run a business. When a corporate takeover pushed Tim out, and a friend showed them you could simply buy a business, they did.
The first year nearly broke them. They priced with “a finger in the air,” had no idea what a good margin was, and kept winning on low bids. Then they found CertainPath — Tim signed up at a Profit Day on the spot — and the turnaround began: fixing their pricing first, then rebuilding sales around an in-home, one-call-close process.
Two years in, they’ve doubled the business past $4 million, they’re targeting $6.5 million, and Tim personally sold $2 million to become a CertainPath roofing crown champion. And it’s 100% woman-owned — Sasha owns it outright, and Tim jokes he’s “just cheap labor.”
In this conversation, you’ll discover:
- How two people with zero trade experience bought a 40-year-old roofing company off a broker
- Why the acquisition was tougher than they expected — and what they’d do differently
- The “finger in the air” pricing mistake CertainPath fixed first
- How moving to an in-home presentation unlocked one-call closes
- Why being the most thorough person at the door — the one who actually goes in the attic — wins the job
- The CertainPath training moment that took Tim from “doing sales completely wrong” to a crown champion
- How they think about growth: taking “a smaller piece of a larger pie”
Whether you run a roofing, HVAC, plumbing, or electrical company, Tim and Sasha’s story shows how to buy a business, raise your prices, and build a sales process that actually closes.
Watch on YouTube or listen on your favorite podcast platform. And don’t forget to subscribe to The Successful Contractor for more interviews that move the needle.
About the Show
The Successful Contractor is a podcast for residential HVAC, plumbing, electrical, and roofing contractors. Hosted by Bob Houchin, each episode features real contractor growth stories, hard-won business insights, and practical takeaways for building a profitable home services company.
Meet the Host
Bob Houchin has spent 20+ years immersed in the home services industry — listening to, learning from, and serving the people who run it. As host of The Successful Contractor, he’s interviewed hundreds of the brightest minds in the trades. Beyond the mic, Bob is a Senior Strategist at CertainPath, building the training, onboarding programs, keynotes, and playbooks used by 1,200+ residential service companies. His motto: smart contractors learn from their mistakes; wise contractors learn from the mistakes of others.
About CertainPath
CertainPath is a business coaching and training organization that has built successful home service businesses for more than 25 years. We serve 1,200+ member companies across HVAC, plumbing, electrical, and roofing with professional coaching, training for every role, software solutions, and a vendor partner network that delivers millions in member rebates every year. Doubling your sales with a 20% net profit and an inspiring company culture is ALL possible. With CertainPath, Success is Made Certain.
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