Craft vs SalesAsk for Roofing Contractors (2026): Six Verticals, One Case Study — Wilson Is Still Not a Roofing Company

Craft’s roofing industry page leads with Wilson.

Wilson Heating, Cooling, Plumbing & Electrical. The same Wilson from the HVAC page. The same Wilson from the Windows & Doors page, the Garage Doors page, the Pool Service page, the Plumbing page. A company based in Ohio that does commercial and residential HVAC, plumbing, and electrical work.

Wilson doesn’t do roofing.

This is the sixth vertical where Craft has deployed Wilson as their primary social proof. The case study is real — 31.4% revenue increase per opportunity, a VP of Sales named Paul Gryniuk who says his techs went from resistant to enthusiastic. None of that is fabricated. It’s just that roofing is not HVAC, and a coaching outcome from an equipment room reveal does not generalize to a storm damage inspection where the sales outcome depends on a three-way conversation between a rep, a homeowner, and an insurance adjuster.

Craft knows this. They built a roofing page. They just didn’t build a roofing-specific case study to go with it.

What Craft’s Roofing Page Actually Claims

The Craft roofing page says: “Record every in-home inspection, coach reps on storm damage presentations and insurance processes in real-time, and increase close rates by 30%+.”

That claim — 30%+ close rate increase — has no roofing attribution behind it. The only case study on the page is Wilson. Wilson is an HVAC company. Their 31.4% revenue increase per opportunity came from coaching HVAC techs through equipment replacement conversations in mechanical rooms and utility areas. Whatever coaching mechanism produced that result, it is not evidence of how real-time coaching performs during roofing inspections.

“In-home inspection” is also a somewhat misleading frame for roofing sales. Some of the roofing inspection conversation happens inside — explaining scope to the homeowner, handling price objections at the kitchen table, reviewing the insurance estimate line by line. But the most consequential part of a storm damage appointment often happens outside, on the property, often on the roof itself. The adjuster doesn’t sit in the living room. The damage documentation conversation doesn’t happen at a kitchen table.

Craft’s earpiece coaching works in structured indoor environments. The HVAC equipment room reveal, where a tech stands in front of a furnace and walks a homeowner through the options — that’s where the real-time coaching architecture makes sense. The rep has both hands free, the conversation has a natural cadence, and the coaching suggestions arrive as whispers while the homeowner is looking at the equipment.

On a roof in the middle of a supplement walkthrough, the dynamic is different. The rep is pointing at damage. The adjuster is writing notes. The homeowner is usually not up there. The conversation is technical, compressed, and contested. A real-time earpiece delivering coaching suggestions in that environment is solving a different problem than Craft’s demos show.

The Wilson Pattern Across Six Verticals

Craft has built industry-specific pages for HVAC, Plumbing, Electrical, Windows & Doors, Garage Doors, Pool Service, and now Roofing. In every case, the featured case study is Wilson.

There’s a legitimate argument that Wilson’s results are generalizable — if coaching increased revenue per opportunity by 31.4% for one home services company, similar gains are plausible elsewhere. But there’s a difference between a general argument and vertical-specific evidence.

Roofing contractors evaluating coaching software don’t want to know whether coaching works in home services generally. They want to know whether it works for roofing specifically — for supplement conversations, for storm inbound CSR calls, for inspector relationship management, for the particular dynamic of selling into insurance-funded work where the payer is a third party with adversarial interests.

None of that is covered by Wilson’s HVAC results. The Wilson story is about techs in mechanical rooms getting comfortable with real-time AI suggestions. The roofing story requires something else.

The Insurance Process Is a Multi-Party Negotiation

Craft’s page says they coach reps on “insurance processes in real-time.” That’s a significant claim that deserves scrutiny.

The insurance claim process for roofing involves a sequence that isn’t fully addressable through in-appointment real-time coaching. The initial inspection happens, the adjuster produces an estimate, the contractor reviews the estimate and identifies items that were undercounted or omitted, a supplement request gets submitted, the adjuster may or may not respond to the supplement, and if they don’t, the contractor escalates through the carrier’s appeals process.

Real-time coaching during the initial inspection is valuable — helping the rep know what questions to ask the adjuster, how to flag damage clearly, how to frame scope discussions before the estimate is locked. But the supplement conversation often happens by phone or email after the inspection, through the carrier’s claims system, over a period of days or weeks. That’s not a real-time coaching environment. It’s a written documentation and negotiation process.

Craft’s coaching architecture is optimized for in-person, real-time appointments. The part of roofing sales that determines job value — the supplement outcome — is partially determined in those appointments but largely resolved in the follow-up process that happens after the inspector leaves.

Connecting coaching to supplement outcomes requires revenue attribution: knowing which coaching interventions correlated with higher supplement approval rates and by how much. That requires integration with the job management system that holds the financial data.

What SalesAsk Brings to the Roofing Conversation

SalesAsk has an actual roofing customer with actual roofing metrics.

Connell Roofing deployed SalesAsk and Coach Dean across their sales team. The outcomes: 19% increase in average project size, 22% increase in average project value, 15% close rate improvement, six hours per week saved for management. Those are roofing numbers from a roofing company, not HVAC numbers deployed as proxy evidence for an unrelated vertical.

Coach Dean’s approach is different from real-time earpiece coaching. Reps record their appointments — inspections, homeowner conversations, follow-up calls — and Coach Dean reviews those recordings to provide specific, line-by-line feedback. Where the rep explained storm damage scope well. Where they fumbled the insurance coverage explanation. Where they moved too quickly past a price objection or left a supplement item unaddressed.

That feedback is available immediately after the appointment, without waiting for the manager to find time in their schedule. For roofing teams where the manager is also in the field during storm season — which is most of them — the ability to get coaching feedback without creating a manager bottleneck is significant.

The ServiceTitan integration connects coaching sessions to actual job outcomes. Supplement amounts, job values, and close rates by rep type — all visible against the coaching record. When you want to know whether the coaching investment produced ROI on a storm season, that attribution exists in a way it doesn’t with Craft’s platform.

CSR coaching covers the inbound surge period that Craft doesn’t address. The virtual ridealong capability extends to full conversation capture across the customer lifecycle — not just the in-home appointment, but the inbound call, the follow-up, the supplement conversation when it can be recorded.

The Connell Roofing case study gives you the specifics of what that deployment looked like in practice. If you want to compare those numbers against what Craft can show for actual roofing deployments, that’s a short conversation — because there aren’t any roofing numbers on Craft’s site. There’s Wilson.

For roofing contractors trying to figure out which AI coaching platform was actually built with their sales conversations in mind, the gap between “we deployed Wilson HVAC as roofing evidence” and “here’s a roofing contractor’s results” is worth taking seriously.

Wilson is a good HVAC company. They’re probably not who you want deciding your supplement coaching strategy.