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The Future-Ready Estimator

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Why Data, Not AI Alone, Will Define the Next Era of Preconstruction

Artificial Intelligence is dominating conversations across construction technology, but according to STACK leaders Ben Coffman and Mike Roy, the companies that gain the greatest advantage won’t necessarily be the ones using the most AI. They’ll be the ones building the strongest data foundation today. 

During a recent STACK webinar, Coffman, STACK’s SVP of Product and Engineering, and Roy, STACK’s VP of Sales, explored what AI means for estimators, why data tenure matters more than most contractors realize, and how construction companies should evaluate technology partners in an AI-driven future. 

AI Is Becoming a Requirement, Not a Differentiator

While STACK continues investing heavily in AI capabilities, Coffman argued that AI will eventually become an expectation, much like mobile technology did years ago. Contractors won’t choose software because it has AI, they’ll expect every serious platform to have it. Instead, the real competitive advantage will come from what sits underneath the AI: data. 

According to Coffman, two factors will matter most: 

The implication is significant. As AI capabilities become increasingly common across the industry, the value shifts from the technology itself to the intelligence generated from years of project data.

What Is a Future-Ready Estimator?

A future-ready estimator is a construction professional who combines experience, judgment, and trade expertise with technology that continuously learns from past projects, estimates, bids, and outcomes.  Rather than replacing estimators, AI serves as an assistant that helps surface insights, identify patterns, and improve accuracy. The estimator remains the decision-maker. 

As Coffman explained: 

We’re here to make the estimator faster, better, and more accurate. We’re here to augment the job. 

That distinction matters. The conversation isn’t about replacing human expertiseIt’s about amplifying it. 

Why Construction Is Ready for Its Next Technology Leap

Roy noted that conversations with hundreds of contractors reveal a consistent theme: excitement. 

Across specialty contractors, general contractors, and estimating teams, there is a growing appetite for modernization. Many firms are still relying on legacy desktop applications, spreadsheets, or disconnected workflows while simultaneously experimenting with tools like ChatGPT and Claude. The challenge isn’t whether AI is coming. It’s understanding how to adopt it strategically. 

“Preconstruction professionals aren’t looking to change their takeoff or estimating process every other year. They want something that sticks for the next ten-plus years.”

That long-term perspective is particularly important because AI is evolving at an unprecedented pace. Features that seem cutting-edge today may become standard tomorrow. The bigger question is whether the platform you’re investing in today will continue creating value years from now. 

Why Data Tenure Matters More Than Most Contractors Realize

One of the webinar’s most compelling themes centered around what Roy called “intelligence that isn’t portable.” Historically, construction companies have evaluated software largely based on features. Can it perform takeoffs? Generate estimates? Create proposals? 

In an AI-driven world, those questions remain important, but they are no longer enough. The real value comes from what the software learns over time.

Imagine an estimator who has worked with a specific developer for 20 years. They know exactly how that customer prefers to receive bids, what details matter most, and where common issues arise.Traditionally, that knowledge lived inside the estimator’s head. Future-ready platforms can begin capturing and learning from those behaviors. As Roy pointed out:

“Intelligence isn’t portable. Intelligence is learned.”

That means every estimate, every bid package, every project, and every workflow contributes to a growing knowledge base that can help future estimators perform better. For contractors facing workforce shortages and retirement waves, the implications are enormous. 

Closing the Knowledge Gap Between Senior and Junior Estimators

One of the most interesting discussions during the webinar focused on a challenge many contractors face today: preserving institutional knowledge. 

The construction industry continues to experience labor shortages and an aging workforce. Many organizations worry about what happens when highly experienced estimators retire. 

Roy believes AI can help bridge that gap. Instead of forcing senior estimators to adopt entirely new ways of working, technology can learn from their behaviors and help transfer those insights to newer team members. Coffman states:

“We want to make something that carries with your most senior people that have all of that intrinsic insight and automatically brings that back down to your more junior people.” 
Imagine a platform that can identify: 
  • Common estimating adjustments made by senior staff
  • Customer-specific proposal preferences
  • Historical bid patterns
  • Frequent scope risks
  • Trade-specific estimating nuances

Rather than replacing expertise, AI helps preserve and distribute it. 

Why the Future Isn't About Faster Takeoffs Alone

Construction technology vendors often focus on automating individual tasks. 

  • Can software draw lines faster? 
  • Can it count symbols automatically? 
  • Can it identify walls with computer vision? 

While those capabilities are valuable, STACK believes they’re only the beginning. Coffman described a future where AI doesn’t simply recognize walls on a plan sheet—it understands the historical costs, assemblies, supplier relationships, and bid outcomes associated with those walls. He said:

“We don’t think of AI as how it will make things better. We think of it as how it will make the preconstruction platform smarter.” 

That distinction separates task automation from business intelligence. Task automation saves time. Business intelligence improves decision-making. The latter is where the greatest long-term value exists. 

The Hidden Cost of Waiting

One of the webinar’s strongest messages was that AI adoption isn’t simply about gaining access to new features. It’s about creating the data foundation required to benefit from future innovations. Because AI systems learn from historical information, companies that begin building their datasets today will have an advantage over those that delay. Coffman states:

“The tenure you have with a company, the amount of data that you have with the company—that’s going to be a differentiator.”

Consider two contractors:

Contractor A

Contractor B

Both companies may eventually access similar AI capabilities, but only one benefits from years of accumulated learning. 

Why Trust and Security Matter More Than Ever

As AI becomes more deeply integrated into construction workflows, data governance becomes increasingly important. Coffman highlighted STACK’s SOC 2 Type II compliance as a foundational element of its approach. And Roy encouraged contractors to ask difficult questions of their technology vendors. 

Questions Every Contractor Should Ask  
“Trust is a really important conversation you want to be having as you’re thinking about your vendor relationships.”— Mike Roy 

Why an Open Ecosystem Wins

Another recurring theme throughout the discussion was interoperability. Rather than forcing contractors into a closed ecosystem, STACK emphasized the importance of integrations and open architecture.

Estimating platforms increasingly need to connect with: 

The future-ready estimator doesn’t work inside a single application. They work within a connected technology ecosystem. As Roy explained, the goal isn’t to become the “Apple of preconstruction.” It’s to ensure data can flow where it needs to go while continuing to generate value. 

The Future of Estimating Is Personalization

Perhaps the most exciting vision presented during the webinar wasn’t about automation at all. It was personalization. Future AI systems won’t simply provide generic recommendations.

They’ll understand:

That means two estimators using the same software may receive entirely different recommendations because the platform understands their businesses differently. That’s where AI becomes truly transformational.

The Bottom Line: The Future-Ready Estimator Starts Preparing Today

The webinar concludes with a simple but important message: innovation is a choice. AI will continue advancing rapidly. New capabilities will emerge every quarter. Automation will improve. But the contractors who gain the greatest advantage won’t necessarily be those chasing every new feature. They’ll be the organizations building strong data foundations, partnering with trusted technology providers, and creating systems that learn from every project. Coffman says:

“The companies you choose to be with is probably one of the most important decisions that you can make.” 

For estimators, that means thinking beyond today’s workflow and considering how every project contributes to tomorrow’s intelligence. The future-ready estimator is helping train the systems that will give their business an advantage for years to come. 

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