Chicagoland agents turn to AI to drive leads and productivity

by Jason Porterfield

From AI-powered marketing and transaction management to data-driven lead generation and client communication, new technology is reshaping the real estate industry across Chicagoland. As agents integrate new tech into their workflows, these tools influence client relationships, productivity and deal flow to deliver real ROI.

A successful tech adoption may require balancing innovation with practicality to keep agents competitive in an increasingly digital marketplace.

For Randi Lynn Quigley of eXp Realty in Manhattan, Illinois, successfully harnessing tech means utilizing social media to generate leads, as well as branching into a new website and creating a digital app to elevate the presence of the Randi Lynn Group.

“I’m open to change,” Quigley said. “I feel like any Realtor who comes into this space really needs to adapt, and it does change very quickly. I feel like it made it easier to get in front of clients. If you’re used to having to grind, a lot of it comes into branding. Even though you’re using tech, it is more important now than ever to create your own brand and lean in on that.”

The website Quigley is building includes AI analytics that enable her to build leads through an AI agent that interacts with the prospective client. AI-embedded advertisements are another shift she is embracing.

“The other thing we’re doing is building out to where someone clicks on our ad, and the AI system knows exactly who is looking at the ads and who’s looking at the house,” Quigley said. “They’re doing all the behind-the-scenes work.”

Hassan Dahik of Coldwell Banker Realty prizes the “granular consistency” he gains through technology.

“I can now centralize every client interaction, maintain organized notes and execute follow-ups at the exact moment they are most impactful,” Dahik said. “Before, much of this relied on memory or scattered notes. Now, I work with a centralized intelligence. It doesn’t replace the human bond. It protects it by ensuring no important detail or milestone is ever left to chance.”

Dahik relies heavily on MRED/connectMLS, as well as a strategic social media presence on Facebook and Instagram and advanced automated follow-up systems. He emphasizes his Google reviews due to the importance of AI-driven discoverability to lead generation.

“I know that when a prospect searches for an agent on Google — or increasingly through AI-assisted tools like ChatGPT Search or Gemini — my online reputation and reviews directly influence whether I am found and how I am perceived,” Dahik said. “To me, reviews are more than social proof. They are a critical component of my digital visibility. However, I firmly believe that without a solid client base and consistent follow-up, it doesn’t matter what app you use. Technology opens the door, but relationships and consistency close the deal.”

T.J. Gosse of Berkshire Hathaway HomeServices Chicago believes technology has made it easier to be proactive in managing his business. He looks forward to the rollout of HomeServices’ Maestro platform, which is designed to streamline workflows using intuitive AI like an agent assistant. He cited the agent-to-client search platform Zenlist as an “essential” tool for helping him grow due to its ability to provide buyers with an opportunity to see properties before the general public.

“With Zenlist, you can go in and see the client activity,” Gosse said. “Then I send out automated market reports, so that gives me insight. When I see somebody click on a property, I can see what they are engaging with in real time. That allows me to do my background research ahead of time. I can anticipate any questions or things that might come up before the client even asks.”

Gosse also utilizes the Remine app to identify potential sellers. “I can go in and see how long somebody’s been living in a house,” he said. “Like if somebody’s been there for 30 years, and then you can see who has a lot of equity in their home, or if someone is an absentee owner, like out of state. It helps me be more intentional with my marketing, instead of just sending out a massive, wide net.”

Maintaining the human side

Gosse cautioned that though tech can streamline business processes, the industry itself remains unchanged in fundamental ways. Traditional lead generation methods such as referrals, repeat clients and the sphere of influence for lead generation still outperform the latest technology.

At the end of the day, the most important thing is still picking up the phone and doing that follow up,” Gosse said. “The relationships are built through trust and consistency, and technology definitely helps with that. But it’s only good if it actually leads to that conversation. Picking up the phone and calling is still the No. 1 tactic.”

Dahik views digital tools not as a replacement for traditional methods, but as a powerful extension of them. Digital platforms allow him to scale his presence and remain “top of mind” within his network.

He regularly uses a tech stack that includes ChatGPT, Gemini, Google AI Studio and NotebookLM, as well as a custom-made CRM and transaction manager he developed using Google AI Studio that he can update as his business needs evolve.

“The real productivity gains come from specialization,” Dahik said. “When you stop using AI as a generic chatbot and start using it as a specialized department of assistants, that is when you truly recover your time.”

Dahik sees a need to proceed with caution despite those productivity gains. “In real estate, an [AI] ‘hallucination’ or an incorrect detail isn’t just a typo, it’s a potential professional liability,” he said. “There are significant concerns regarding ethics, data privacy and the risk of losing the human touch. AI can amplify efficiency, but it must never replace an agent’s professional judgment, experience or accountability. Speed is a luxury, but accuracy remains a necessity.”

Quigley believes existing tech aligns well with referrals and the sphere of influence but will not replace those more traditional lead generation tools.

“I feel like your sphere of influence and past referrals will always be your No. 1 source of lead generation,” Quigley said. “I always add my lead source, or all my friends and family and past clients, to my social media and to my ad campaigns. There’s so much AI out there, so it’s good for people who really had an experience with you to vouch for you. Nowadays, unfortunately, you don’t know whom you’re talking to. So, if you have someone who’s actually done a transaction with you, that’s the most powerful referral of all.”

AI and agents

Despite recent advances in AI technology, Quigley is quick to dismiss the idea of its taking the place of agents.

“I don’t think it’s actually going to replace agents, but there are so many things that we can do to lean in on it,” she said. “The website that we’re building right now has AI in it. Basically, it has analytics. When someone clicks on our site, the AI agent is actually able to go in there and speak with them on our behalf. Once the lead is generated enough or it actually feels like they’re ready to talk to us, that’s when we’ll connect. It’s a good way of freeing up your time a little bit.”

While AI frees up time, agents still have to make sure they follow ethical and professional guidelines when working AI-generated leads. If the lead clicks on an ad with embedded AI, Quigley said, it’s fine to contact them. If they ask to be removed, the agent has to remove them.

“For the most part, it’s one of those things you actually physically talk to them and you confirm everything that they’ve said,” Quigley said. “We’re just using [the AI agent] to literally get in front of people and start the discussion. Once that discussion started, or we know that they’re actually looking to buy or sell, that’s when we take over the conversation. So, we’re using AI as the tool. They’re not going ahead and discussing details of properties and searches and their process with the clients.”

Dahik utilizes his tech platforms to “reallocate” his energy but considers relationships to be the core of his business.

“Technology handles the operational weight — the paperwork and the repetitive follow-ups — so that I can focus on the most important part of my business: prospecting,” Dahik said. “It allows me to dedicate 100% of my human energy to building relationships and staying present with my database … Technology allows me to be more efficient, but this business still grows through relationships, trust and a strong database,” he said. “Without consistent follow-up, no app is going to build the business for you.”

Gosse agrees that AI is a valuable tool for saving time, but that agents need to be wary of simply generating content for their clients rather than guiding them through the transaction.

“We can use AI to save time and get us started, but AI should support your voice,” Gosse said. “It should not become your voice. I think a lot of agents have run into that.”

As a user of ChatGPT, Gosse acknowledges that the app can be “pretty agreeable at times, instead of completely accurate,” a point agents should heed if they want to generate accurate content.

“Accuracy matters too much in real estate to just copy and paste what AI gives you, whether it’s pricing language or market insights or neighborhood context or whatever,” Gosse said. “It just still needs that human expertise. From the ethical side, if agents are relying so heavily on AI that they’re just copying and pasting, then the client isn’t actually getting the advice that’s specific to them.”

Expert Sources

Randi Lynn Quigley

eXp Realty

Hassan Dahik

Coldwell Banker Realty

T.J. Gosse

  Berkshire Hathaway HomeServices Chicago

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