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Oppy Wins RISMedia’s 1st Annual Tech Showdown

The AI-driven platform that launches virtual assistants called “Oppies” rose to the top after an extremely tight race among the finalists.

Home Industry News
By Beth McGuire
January 20, 2026
Reading Time: 6 mins read
Oppy Wins RISMedia’s 1st Annual Tech Showdown

The results of RISMedia’s first annual Tech Showdown are in, and Oppy, the AI-driven platform that launches and manages personalized AI assistants called “Oppies,” rose to the top after an extremely tight race among finalists. A three-way tie among judges was tipped in Oppy’s favor from votes cast by RISMedia viewers who tuned into the live pitch-battle webinar on Jan. 14. 

“At Oppy, we’ve been focused on building a platform where residential service businesses like brokerages can deploy AI agents at scale, complete with the control and oversight these entrepreneurs need,” said Alex Gustafson, founder and CEO of Oppy after being selected the winner. “Winning the RISMedia Tech Showdown is a major milestone for Oppy as it recognizes that this isn’t a future concept anymore—it’s an operating advantage for winning executives right now.”

The three Tech Showdown finalists—Oppy, Fiji App and Courted.io—presented their solutions to webinar host, RISMedia Founder & CEO John Featherston, along with industry leaders Kate Reisinger, COO, Leading Real Estate Companies of the World®; Joe Rand, chief creative officer, Howard Hanna | Rand Realty; and Cory Vasquez, president and CMO, Realty ONE Group, who served as competition judges. Several hundred RISMedia viewers who tuned in were sent a poll after the event asking them to cast a vote for their favorite contestant. 

During a three-minute pitch, Gustafson shared the high-level features and benefits of his company’s AI assistant, which include:

– Deploying intelligent AI assistants at scale with enterprise-grade management and control
– AI assistants working 24/7 to handle routine tasks like lead qualification, scheduling, customer support and follow-ups
– AI assistants managing multiple communication channels, including web chat, text messaging, voice calls and email, while maintaining natural, engaging conversations, and ensuring a 3.5-second response time. 

“The main problem we’re trying to help people with here is nobody wants to answer the same questions over and over regardless of your vertical,” Gustafson said during the pitch battle. “Especially in real estate, there’s a lot of questions that are very low-hanging fruit that brokers have to answer for their agents, that agents have to answer for their leads, and a lot of that can be automated so that each person on your team can focus on what’s adding value.”

According to Gustafson, what makes Oppy special is its “Human-in-the-Loop” approach, where AI assistants handle routine inquiries, but intelligently escalate important matters to human agents when needed. Across the industry, he said some agents are using multiple Oppies together to assist with business tasks both that the program was designed for and also in new ways the creators hadn’t thought about. 

“You could have one or a thousand,” he said. “Let’s say you want to answer top-of-funnel leads that come in and nurture ones from your (CRM). You start there, but as your team grows over time, Oppy provides that ‘Human-in-the-Loop’ dashboard experience so that your team can join your AI employees. Oppy agents work with them in a variety of different ways. We build everything from the standpoint of what a person sitting at a desk could do if you were to hire them. We see a lot of our customers prompt their own and come up with things I never even thought were possible like AI Santas or a scary witch on Halloween to share with customers.”

During the pitch battle, Vasquez asked Gustafson how Oppy addresses “AI fatigue,” where consumers recognize and are turned off by AI-driven outreach. Gustafson said it’s all about the content. 

“If what you’re telling someone is quality content and they get it almost immediately, then the consumer doesn’t care as much, so we give all our Oppy agents all the tools they need to get the context they need,” he said. “So if it needs to learn something before it responds, it will go figure it out before responding. If it needs to generate a postcard to send to somebody it can go (do that) and include something about the area where you’re looking to move to and send a hand-written note. So it’s really meant to augment and work with agents instead of replace them. Brokers are figuring out how to make these personalized and give them personality and make them enjoyable to talk to and drive value that way.”

Reisinger asked to hear some real-world examples and metrics of the return on investment (ROI) Oppy has provided to brokerages. 

“Some are really heating up how they use phone calling and how they’re responding to leads,” Gustafson said. “We are seeing that warming up an old list; some people are getting between 1% and 3% conversions out of very, very old lists.” 

He also said some clients are saving 6,000 hours a month, “which is insane, but if you truly look at the time spent on the phone, the time spent writing text messages, things like that, Oppy is able to remove that, so there’s tremendous ROI there as well.” 

In terms of lead conversion, Gustafson shared: “If they’re coming in from top of funnel, Oppy will reach out almost immediately—typically the calls go very well and at that point, people are seeing about 10%-20% will actually schedule an appointment.”

Rand asked Gustafson to drill down on the level of engagement Oppy can provide. For example, is it better used for old lists of contacts an agent may never personally engage with, or is it sophisticated enough to intelligently engage with active, personal contacts, or as Rand put it, “My best friend to see if they know of anyone who’s thinking of moving.”

“You can prompt it to have a nuanced backstory about your town or your area of focus; you can make it as personal as you want,” Gustafson said. “I’m a creative (person) and I don’t want to talk to some bot either. We’re really targeting human speech. Some of the ones we’ve built, they’re fun to talk to.” 

He said the “outersphere,” or leads where there isn’t a personal relationship, is the recommended starting point and over time users learn how to make their Oppy more personalized to their business needs.

In comments recapping each solution after the presentations, Reisinger said Oppy “bridges the gap” between other virtual assistants out there and a full CRM. “I think there’s a nice need for that in the marketplace,” she said.

“I think the applications for (Oppy) are really extraordinary,” added Rand. “For saving time, for getting agents to do things we know they should be doing but they don’t because they don’t like to do it. The hardest part of this job is calling people that you don’t know and asking them follow-up questions and trying to get their business…knowing an AI assistant is doing this for you, is fearless and doesn’t care about rejection, really does serve a need that agents have.”

Vasquez concluded, “My favorite part about Oppy was putting real data to what they’re doing. If you can actually say you’re going to save 85% on time and resources, that to me is so substantial—you can’t not look at Oppy as a solution.”

The three finalists and winner were chosen by the expert judges along with RISMedia editors and technology executives using a point evaluation system based on the product’s uniqueness; its value proposition to brokers and/or agents; its potential to scale industry-wide; the clarity of recorded and/or live presentations; and several other factors. 

As the winner, Oppy will receive dedicated editorial via RISMedia’s platforms, a Product Showcase Webinar produced by RISMedia to demonstrate the technology’s potential impact on brokers and agents, and an extensive advertising campaign valued at more than $80,000.

Tags: AI AssistantAI-driven real estate platformAlex GustafsonArtificial Intelligence in Real EstateCory VasquezJoe RandJohn FeatherstonKate ReisingerOppyRISMedia Tech Showdown
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Beth McGuire

Beth McGuire is RISMedia’s vice president of online editorial.

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