Future of AIAI

From “My Usual” to Strategic Advantage: Why Personalization is the Real Promise of AI

By David Stifter, CEO and Founder, PredictAP

When I was growing up, Friday mornings meant breakfast at Bob’s Big Boy with my dad. Same booth, same order. Hashbrowns extra crispy, eggs sunny side up, toast lightly browned, coffee with a side of ice cubes. But here’s the thing: he never had to say all that. He just smiled at the waitress and said, “I’ll have my usual.” 

That little phrase carried years of shared understanding. It was more than shorthand; it was trust. The waitress already knew the quirks, the exceptions, the details that made the order right. 

That’s exactly what AI done right should feel like in business. 

From Bottleneck to Growth Engine 

In most real estate organizations large or small, and in many other business types, tribal knowledge shapes how work really gets done. In accounts payable, for example, it is knowing which vendor invoices are partly recoverable, how to split a utility bill across properties, or which cost codes should override the defaults. Traditionally, this expertise lived in people’s heads and took years to train. 

AI changes that. Modern systems don’t just automate data entry; they learn the context. They observe patterns across thousands (or millions) of transactions and start to “get it right” even when information is incomplete. It’s as if the system already knows your “usual.” 

For decades, AP in real estate was viewed as an administrative chore. More properties meant more invoices, more staff, more cost. Growth was linear, and limited by the capacity of available staff and the reality of the 40-hour work week. 

AI severs that link. Instead of simply speeding up keystrokes, it makes judgment calls: applying nuanced vendor rules, interpreting exceptions, and scaling decisions the way a seasoned staffer would. The impact is profound. 

Firms that once waited more than ten business days for invoices to clear now close cycles in three. 

PEG Companies increased invoice volume by 125% without adding headcount. As AP Manager Alicia Pulley put it: “We have the capability to do additional invoices without extra people on my team. We just have an extra tool with AI that makes it much easier.” 

Unlocking Strategy Through Personalization 

The real power of AI isn’t just efficiency, it’s insight. When exception-handling and coding rules become structured and repeatable, patterns emerge that executives can act on. 

A community’s maintenance costs may be outpacing others. 

A vendor could be charging inconsistent rates across markets. 

A particular expense category might be quietly eating into reserves. 

These aren’t one-off discoveries anymore; they’re the natural byproduct of day-to-day processing. Suddenly, AP rolls stop being transactional and start becoming a strategic asset. 

Executives can negotiate vendor contracts from a position of strength, adjust budgets dynamically, and model acquisitions with greater confidence. Property managers shift from firefighting backlogs to strengthening tenant relationships. Finance leaders can see not just where the money went, but where it’s going. 

Why This Matters Right Now 

Margins in real estate are being squeezed from every direction: labor, insurance, utilities, compliance. In that environment, the ability to scale without scaling cost is no longer optional, it’s existential. AI doesn’t just deliver efficiency; it embeds resilience, foresight, and transparency into the finance function. 

What was once the quietest corner of the back office is now a lever for growth. 

And just like my dad’s order at Bob’s Big Boy, the firms that win with AI will be the ones whose systems already know their “usual,” and can turn that understanding into decision-making action at scale. 

About the author: David Stifter 

David has 20+ years of experience developing business applications for financial and real estate companies. He led the technology side of the project that would become PredictAP a market leader in real estate invoice coding, and leveraged his deep expertise of real estate and finance business pain points to envision a unique solution. He holds an MBA from Boston University. 

  

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