Randy Ripkey Says AI Should Make It Easier, Not Harder, to Reach a Person
Answering service industry veteran Randy Ripkey says AI can improve customer service, but businesses should make
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Answering service industry veteran Randy Ripkey says AI can improve customer service, but businesses should make transparency, human access, and smooth handoffs part of the process.
JACKSONVILLE, FL / ACCESS Newswire / October 14, 2026 / As artificial intelligence becomes more common in customer service, answering service industry veteran and software developer Randy Ripkey believes businesses should pay just as much attention to the caller experience as they do to the technology itself.
Ripkey has worked in the telephone answering service industry since 1995 and began selling billing software to the industry in 2000. After decades of watching communication technology evolve, he sees AI as another useful tool, but not one that should make it more difficult for callers to get the help they need.
“AI is moving fast, and it is not going away,” Ripkey said. “The question is how we use it in a way that actually improves the experience for the caller.”
Callers Should Know When They Are Speaking With AI
One of Ripkey’s priorities is transparency.
While experimenting with an AI answering agent, he made the decision to have the system identify itself as AI. He sees little benefit in trying to convince callers that they are speaking with a person.
Setting that expectation at the beginning of the conversation can also affect how callers interact with the system. People may communicate differently when they understand they are speaking with an automated assistant.
Ripkey believes transparency will become increasingly important as AI voices and conversational systems become more realistic.
“The goal shouldn’t be to fool somebody,” Ripkey said. “If AI can handle what the caller needs, that’s useful. If it can’t, there should be an easy way to move on.”
Avoiding ‘Automation Voicemail Jail’
Ripkey is particularly wary of systems that leave customers trapped in layers of automation.
He describes the experience as “automation voicemail jail,” where a caller keeps navigating prompts or repeating requests but cannot find a straightforward way to reach a person.
It is an experience he has encountered as a customer himself, and one he does not want AI to recreate.
In the AI system Ripkey has tested, callers have the option to request a live agent. He believes that kind of escape route is important because not every conversation is a good candidate for automation.
A caller may have an unusual question. The system may misunderstand what is being said. Background noise may interfere with the conversation. Sometimes a caller simply wants to speak with another person.
AI does not have to handle every situation for it to be useful.
A Human Handoff Should Not Mean Starting Over
Giving callers access to an employee is only part of the process. Ripkey also points to what happens during the transfer.
If an AI system has already collected a caller’s name, contact information, or reason for calling, that information should move with the conversation when possible. Otherwise, the caller reaches a live agent only to be asked the same questions again.
That may sound like a small inconvenience, but Ripkey says these details matter.
A good handoff should allow the employee to see what has already happened and continue the conversation from there. The technology becomes less useful if it saves time during the first part of the call but creates additional work during the second.
For answering services in particular, Ripkey believes that distinction matters. Operators frequently represent other businesses when answering calls, making the caller’s experience an important part of the service they provide.
Testing AI Before Putting It in Front of Callers
Ripkey’s views come partly from his own experience introducing AI into an answering service environment.
Rather than immediately deploying the technology on customer accounts, he created a separate test account and spent weeks experimenting with it.
The testing exposed questions that are easy to overlook in a demonstration. Ripkey looked at how the system responded to pauses, background noise, unexpected answers, and other ordinary parts of real telephone conversations.
That process reinforced his belief that businesses should test AI based on what real callers actually do rather than what a system can accomplish under ideal conditions.
“Is it perfect? No,” Ripkey said. “But it’s getting better all the time and it’s moving fast and it’s not going away. Let’s learn how to use this technology and take advantage of it.”
For Ripkey, taking advantage of AI does not mean removing people from every interaction. It means determining where automation can genuinely help and making sure there is a sensible next step when it cannot.
As answering services continue experimenting with AI, he expects the technology itself to improve quickly. The more lasting question may be whether the systems are designed around the people who ultimately have to use them.
About Randy Ripkey
Randy Ripkey is a Jacksonville, Florida-based entrepreneur, software developer, and longtime telephone answering service industry professional. He entered the answering service business in 1995 and began selling billing software in 2000. Ripkey operated Accurate Messages for more than 30 years and is president of TAS Concepts, Inc., the company behind TASbiller and TASbillerCloud.
Ripkey has also held leadership roles within the answering service industry, including serving as president of the Southern Telemessaging Association and on the Board of Directors of the Association of TeleServices International (ATSI). He received the ATSI President’s Award in 2023. His work focuses on answering service operations, software, billing and analysis, profitability, emerging technology, and practical applications of AI.
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