John Kenney, CPRC, CEO, Cotney Consulting Group - January 2026
Roof estimating has always been a mix of numbers, field knowledge and instincts that come only from years of real work experience. Long before software entered the picture, strong estimators built their reputations on accuracy, consistency and the ability to see the entire project before a crew set foot on the roof. That core part of the trade hasn’t changed. What is changing is the volume of information available to us and the tools we now have to manage it. Artificial intelligence is beginning to influence estimating and whether we embrace it early or wait to see how it matures, it’s clear that AI will play an increasingly important role in how roofing contractors operate in the coming years. The real question isn’t whether AI has a place in estimating. The real question is how it fits and where the estimator’s judgment will continue to matter most.
To understand AI’s role, you must first recognize how estimating has traditionally worked. Every estimator carries a mental catalogue of past jobs. You remember how production went on the last school reroof. You know how long the detail work was dragged out on a retail strip center. You recall which crews move quickly on wide-open squares and which ones excel at complex penetrations and equipment curbs. Over time, these observations turn into patterns. You learn what slows you down, where profit tends to evaporate and what conditions require more caution. That part of the craft won’t disappear because no software model, no matter how advanced, can replace the judgment developed through years of walking roofs, managing crews and solving real problems in real time.
What AI can do is expand the number of patterns you’re able to recognize. Instead of relying on memory and scattered notes, AI can analyze years of completed work. It can review weather history, roof layout, deck conditions, tear-off challenges, crew behavior, delivery timing, staging limitations and dozens of other variables that might otherwise fade from memory once a job is closed out. It doesn’t get tired. It doesn’t forget. It doesn’t overlook small details that slowly erode productivity. Used correctly, AI becomes another set of eyes, one capable of studying the kind of job data most companies never have had time to organize.
But AI is not a magic solution and it won’t hand you perfect answers. Its value depends entirely on the quality of the information you feed it. If job costing is inconsistent, production reporting is incomplete or changes in scope are never accurately captured, AI will reflect those gaps. Data discipline becomes more important when you rely on technology to support your decisions. The estimator still drives the process. If the inputs are weak, the insights will be too.
AI’s most meaningful contribution will likely be in forecasting. Estimators already predict labor requirements, production rates, risk exposure and schedule impacts. Those predictions are grounded in experience and judgment. AI strengthens those predictions by digging into your historical data and revealing patterns you might not notice on your own. It may show that your detail crew performs differently depending on who supervises them. It may indicate that specific roof geometries consistently take longer than your team typically budgets. It may highlight how weather patterns in particular regions slow production more dramatically than expected. These insights aren’t meant to override your decision-making. They sharpen it. The estimator still chooses the number but can do so now with a clearer understanding of the risks behind it.
AI will also reshape how roofing companies plan for the long term. Leaders will begin using data trends to understand which types of work deliver the strongest margins and which ones repeatedly strain operations. Service departments will identify the most common repair patterns in their geographic area, not just from memory but from real historical data. Project managers will see early warnings when production drifts off pace. Over time, this level of visibility will influence how company’s staff, schedule and allocate resources. In that sense, AI becomes a spotlight, not a replacement. It illuminates what’s happening in the business, enabling leaders to make informed decisions.
Even with these advancements, AI isn’t likely to eliminate the human element of estimating. Roofing remains a complex, variable environment. Every project has its own personality. Some start slow and finish strong. Others begin smoothly and unravel near the end. Models don’t read a roof the way an experienced estimator does. They don’t understand how a building owner negotiates. They don’t recognize the subtle cues that tell you a subcontractor may be overpromising. They can’t look at a site setup and intuitively know that material flow will slow production. They don’t feel the shift in momentum when the weather turns or manpower drops. These human observations remain central to how estimates are built and how projects succeed.
The estimators who thrive in the future will be the ones who use AI without surrendering their judgment. They will rely on AI to analyze the data but they’ll still determine the outcome. AI may help quantify risk but it doesn’t remove it. It may help identify patterns but it doesn’t have the experience to interpret them. The estimator remains the one who sees the whole picture, weighs the unknowns and ultimately signs his name to the number.
Contractors should also view AI as a training tool. New estimators entering the industry lack the backlog of lived experience that seasoned estimators bring. AI can help shorten that learning curve by showing them historical production data, identifying patterns of past overruns and illustrating why certain decisions lead to specific outcomes. Instead of learning exclusively through trial and error, new estimators can learn from your company’s own history. AI can highlight lessons that might otherwise take years to discover.
As AI becomes more common, contractors will face different challenges, like choosing tools that actually help. The market will be filled with software companies who claim they can transform your business. Some tools will provide real value; many will not. Before investing, contractors should ask whether the technology improves estimating accuracy, streamlines workflow, reduces errors or strengthens project planning. Technology that complicates your process or overwhelms your team will slow you down, not move you forward.
Five or ten years from now, AI will feel like a standard part of the estimating process, just as digital takeoffs do today. The companies that benefit most won’t be the ones with the flashiest software. They’ll be the ones who pair technology with craftsmanship. They’ll maintain clean job records, invest in training, walk roofs, communicate with crews and make decisions grounded in real-world understanding. AI will give them clearer insight but it won’t change who’s responsible for the call; it will simply provide better information to assist in an informed decision.
The future of roof estimating belongs to the contractors who embrace AI as a tool not as a shortcut. Companies that succeed will blend technology with judgment, pattern recognition with experience and forecasting with field reality. Estimating has always been about seeing what others miss. AI gives you an additional perspective. The insight and the responsibility remain firmly in the estimator’s hands.
John Kenney, CPRC is CEO of Cotney Consulting Group, Plant City. He has decades of experience on commercial roofing projects, providing him with a unique understanding of what it takes to succeed in roofing – on the roof, in the office and at scale. John saw the need to provide contractors with strategic guidance built on real-world field knowledge. Cotney
Consulting offers COO on Demand, online training, technology solutions, business advisory consulting, collections, contracts, Castagra estimating training, safety and OSHA training. John partners with FRSA to provide educational seminars. For more information, contact John at jkenney@cotneyconsulting.com or 813-851-4173.