From left: heyLibby co-founders Anna Rodriguez; Spencer Rascoff; and Tony Small. (heyLibby Photos)

Spencer Rascoff, Anna Rodriguez, and Tony Small spent years figuring out how to help small businesses convert leads into transactions when they worked together at Zillow Group.

Now they’re teaming up again to solve the same problem — with a boost from generative artificial intelligence.

The former Zillow colleagues are the co-founders of heyLibby, a new Seattle startup that aims to help owners of small and medium-sized businesses automate initial conversations with prospective clients.

The company’s free-to-use chatbot, powered by an API from ChatGPT-maker OpenAI, acts as a virtual assistant that responds instantly, gathers information, sets up appointments, and produces a conversation summary for business owners. It can be used within social media profiles or on a website.

Potential users include realtors, general contractors, event planners, hair stylists, personal trainers, and others who respond to leads.

heyLibby is the latest example of a startup using advancements in AI to automate mundane tasks.

“The idea is to help these SMBs answer the same questions and turn a DM into a qualified prospect,” said Rascoff, who helped start Zillow in 2005 and was CEO until 2019. He incubated heyLibby out of his Los Angeles-based firm 75 & Sunny Labs and is the company’s sole backer.

Rascoff said he’s using heyLibby to field inbound messages from startups seeking investment and entrepreneurs wanting business coaching advice.

My conversation with Rascoff’s heyLibby bot.

Jeff Elson, a real estate photographer out of Los Angeles, is testing heyLibby and found a few new clients using the software. He said he typically lets phone calls go to voicemail because he wants to know more about a potential client before speaking with them.

“I’m using it as a filter for incoming potential new business,” he said.

A common critique of chatbots such as ChatGPT is that they hallucinate, or generate false information. Some people have also had disturbing conversations.

heyLibby is designed to only answer questions related to the services provided by the business.

“It’s really good about not answering things that it really shouldn’t,” said Rodriguez.

Jeff Elson’s heyLibby did not want to answer my non-related question about AI and philosophy.

The company lets business owners customize the bot’s questions and answers. They are notified each time the bot interacts with a customer and get detailed information about each conversation.

“Linktree meets ChatGPT meets Calendly — with a little bit of Salesforce thrown in,” Rascoff said of heyLibby.

Rascoff expects that all small businesses will use AI in some form when communicating with prospects.

“I’m pretty sure every business is going to have something that qualifies consumers and gets them deeper in the funnel before a human gets involved,” he said.

heyLibby — which stands for “link in bio” — plans to generate revenue by offering premium add-ons and services.

There are various chatbots used by companies for their own customer service needs, but Rascoff said heyLibby is unique in its focus on SMBs.

Rodriguez said while the company relies on OpenAI’s API today it may develop its own large language model in the future.

Rodriguez worked at Zillow for more than four years, leading teams that managed third-party applications such as Salesforce and Zendesk. She later joined Slalom and was most recently a director at Avalara before taking the startup leap with heyLibby.

Small spent more than eight years at Zillow, where he oversaw the company’s core Premier Agent business that helps realtors advertise and find leads on the real estate platform. He also spent five years at Amazon before joining Zillow and was the chief revenue officer at Convoy, Pro.com, and Wiliot.

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