Why Modern Dental Offices Are Ditching Paper Payments for AI-Ready Systems

By Sam Rockwood ・ November 20th, 2025

Economics students for years to come will study the speedy evolution of the mobile phone, starting circa 1999. You will recall the original peanut-looking Nokia phones. Tiny screen, only used for calling, texting and playing snake game. Then we moved to flip phones which had a larger screen. More texting, slightly more sophisticated games, more snake game, and starting to get web access. Then came a full keyboard for easier texting and messaging. Email access on the mobile phone became commonplace. Blackberries and the like exploded. Then, in 2007, the ‘look’ of the mobile phone stopped evolving.

In January 2007 Steve Jobs began a MacWorld presentation explaining that the hardware of the mobile phones of the day was limiting the software. Requiring the use of physical buttons, however many you put on the phone, would still hinder software innovation. What if a developer wanted to create an application that required a type of button that wasn’t on the keyboard? Impossible.

So Apple announced the iPhone with the first touchscreen.

By eliminating the keyboard, the possibilities for software innovation exploded.

Can you imagine using Google Maps or photo editing apps on a phone with a keyboard? So many of your favorite mobile games you play today could never have existed without the invention of the touchscreen.

The rest is history. Obviously, there has been innovation since 2007, but the look and feel of the mobile phone has not changed. Mobile phone manufacturers had to choose to chase Apple and innovate with their own version of a touchscreen or stick with the buttons. As Jobs predicted, the software continued to evolve and companies like Blackberry and those that chose to stick with the buttons died out.

How does this relate to dental insurance payments in 2025?

The most talked about innovation in our day is clearly artificial intelligence. But AI today is limited to only being useful for digital systems. If you are receiving paper payments and EOBs, you are holding on to that Blackberry with the keyboard buttons. And just as mobile phones with a keyboard could not run apps meant for a touchscreen, you will miss out on future innovations made possible by moving your claim payments to digital.

AI will clearly change so much about our world, in particular how we work. I am not an AI expert. However, after nearly 20 years working in healthcare analysis and systems, I am a healthcare data expert. At their core, Large Language Models (LLMs) that run our AI tools are functions. They take data in, apply a set of probabilities and algorithms, and spit results out.

Everyone who works with functions, albeit analysis, LLMs, forecasts, etc., knows that the quality of the output is highly dependent on the data that goes in.

You can’t input minimal or faulty data and expect to get accurate results. In data analysis, this is commonly referred to as GIGO (garbage in, garbage out).

What would happen if you ask your ChatGPT prompt, “Where socks?” Open AI may have access to all the data in the world about sock manufacturers and retailers, the history of socks, the cultural uses of socks. But with the minimal data you’ve given it, the algorithm can’t know if you are asking where you can buy socks, where socks were invented, where socks are typically worn OR are you asking ChatGPT where your own socks are because you can’t find them?!

What type of AI or tech automations could work on my payment systems?

A great question. No one fully knows what the future will hold. When Steve Jobs introduced the touchscreen did he know that hundreds of millions of people would play Angry Birds? I’m guessing not. I can provide a few automations that are here now and coming in the near future. But it is clear that any future automations or integrations with AI will require digital, not paper-based, data.

1. Claim Payment Posting

While you spend hours every week collecting the mail, opening the checks, manually entering the paid amounts in your PMS and depositing the checks, there are a growing number of practices that do all this with the push of a button. This month Woods is rolling out Claim Payment Posting which provides all the info you need to reconcile your payments AND if all looks good, the payment amounts are written to your practice software with the push of a button.

2. Claim Status Check

If you are awaiting a claim payment, is it because the mailman is taking too long or because the payer needs more info? If your payments and communications are digital, systems can be put in place to help eliminate the wait on claim payments.

3. Instapay

AI tools will soon allow us to determine the probability that a submitted claim will be fully paid. Many claims that are sent in are repetitive or mundane and as such should be expected to be paid nearly 100% of the time. Much like an employee getting access to their paycheck days in advance, payment companies can make claim funds available instantly for providers under these circumstances.

This is just scratching the surface and as AI and other tooling becomes more advanced, the possibilities are endless for how rote office work can be automated and providers can focus more of their time and attention on patient care.

If converting all your claim payments and EOBs to digital sounds overwhelming, let Woods handle the transition for you. Our secure platform and elite onboarding team get all the info needed in a 30 minute onboarding session.

Schedule a Demo

It’s Time to Modernize Your Insurance Payments

By Sam Rockwood ・ April 29th, 2025

There are an estimated 340 million dental claims reimbursed by insurance every year in the US. In 2024, 70% of those were paid via a check or similar payment—sent in the mail. Because each mailing also includes paper EOBs, we’re talking about an estimated 360 million sheets of paper wasted annually on dental checks and EOBs—that’s nearly 1 million sheets per day!

C’mon, it’s 2025. We can do better.

Who still uses checks?

I haven’t written a personal check in years. They’re slow, prone to theft, and require unnecessary manual work. But that’s not even the main reason I don’t use them. I don’t write checks because the people I’m paying don’t want them.

According to a recent CAQH study, 70% of payments from insurance to dental providers are manual (i.e., not electronic). But not all of these are checks—some are even worse. They’re the dreaded… virtual credit cards (VCCs). The only thing a dental office likes less than a check is a virtual credit card. Not only do VCCs also arrive in the mail (still wasting time, paper, and postage), but when an office accepts them as payment, they lose 3-5% of their revenue to credit card processing fees. That means if your office is getting paid via VCC, you could be throwing away thousands of dollars every month in avoidable fees.

There’s a better way

Do you remember back in the day when you had a part-time job and you’d pick up a paper paycheck from the breakroom every two weeks? Then, remember how great it was when you started getting paid direct deposit? No paper, no delays, no extra steps. Why isn’t it the same for dental payments?

This isn’t new tech. Electronic Fund Transfer (EFT) has been around for over 50 years. Your office can eliminate the wait for checks and avoid VCC fees entirely by switching to EFT payments—direct from payer to bank, instantly.

Have you tried to set up EFT payments through a third party only to find out they are (like VCC) taking a % of the payment? This can be avoided! Fee-free EFT can be set up directly with the payer. In fact, HIPAA requires that every health plan offer fee-free EFT payments to providers. This is why the ADA has been advocating for dental offices to switch to EFT for years.

EFT is also more secure than payments by mail. Almost every dental office I’ve talked to has a story about checks being stolen out of their mail.

A young entrepreneurial dentist recently relayed an experience she had of heading to the ATM to deposit a handful of insurance checks, something she had done dozens of times before with $20,000 or more in insurance reimbursement. This time, however, there was a bank error in the process which rendered the checks shredded and nothing deposited into her account!

After weeks of back and forth with her bank and the insurance companies she finally was able to recoup the money, but this is the moment that led her to wonder aloud, “Why in the world are we still being paid with checks?”

So if EFT is faster, cheaper, and more secure, why are only 30% of dental insurance payments processed this way?

EFT

30% of Payments *

• Difficult to enroll

• Tedious to reconcile

*2024 CAQH study

Checks in the Mail

50-60% of payments

• 2-4 week delay

• Low security

• Waste of paper and postage

Virtual Credit Card

10-20% of payments

• 3-5% interchange fee

• Waste of paper and postage

Why hasn’t EFT taken over?

After meeting with hundreds of dental offices, it’s clear that most dental staff understand EFT is faster, more secure, and cost-saving. But many don’t know how to enroll or even realize it’s an option.

Even for offices that have switched some payments to EFT, there’s a major drawback: No more mailed EOBs. Instead, you have to hunt them down across multiple payer portals, logging into different systems just to reconcile payments.

As one office manager put it: “My dentist prefers EFT so the payment arrives faster, but I prefer checks so I can reconcile easier.”

EFT made easy with Woods

It’s time to modernize your insurance payments.

Woods has built a simple, seamless platform that brings all your EOBs into one dashboard—no more wasting time digging through portals, faxes, or mail. In exchange for getting your office off of VCCs and reconciling quickly, Woods charges a small fee per claim that is surfaced to the dashboard.

Sam Rockwood is founder and CEO of Woods. After spending 17 years as an actuary analyzing claims data for insurance and tech companies, he founded Woods to improve cash flow for dental offices and to save some trees. When he’s not digitizing archaic payment systems, Sam likes to watch college football, go running, and play NERF guns with his 5 boys.