When they collaborated at Zillow Group, Spencer Rascoff, Anna Rodriguez, and Tony Small spent years working out how to assist small businesses turn leads into deals.

They are now working together once more to address the same issue, this time with assistance from generative AI.

The co-founders of heyLibby, a recent Seattle startup that wants to assist owners of small and medium-sized businesses automate preliminary talks with potential customers, are former Zillow coworkers.

The company’s free-to-use chatbot functions as a virtual assistant that answers immediately, gathers information, schedules appointments, and provides business owners with a discussion summary. It is backed by an API from ChatGPT developer OpenAI. It can be applied to websites or social media profiles.

Realtors, general contractors, party planners, hairdressers, personal trainers, and other lead responders are examples of potential users.

The newest example of a startup harnessing advances in AI to automate routine chores is heyLibby.

Rascoff, who assisted in founding Zillow in 2005 and served as CEO until 2019, said, “The idea is to help these SMBs answer the same questions and turn a DM into a qualified prospect.” He is the only investor in heyLibby and founded it out of his Los Angeles-based company 75 & Sunny Labs.

Rascoff claimed that he uses heyLibby to handle incoming communications from startups looking for financing and business owners seeking assistance.

My exchange with the heyLibby bot from Rascoff.
Los Angeles-based real estate photographer Jeff Elson is evaluating heyLibby and has acquired a few new clients as a result. He claimed that he frequently leaves voicemail messages from potential clients be left because he wants to learn more about them before speaking with them.

I’m using it as a filter for prospective new business that comes in, he explained.

The idea that chatbots like ChatGPT produce erroneous information or have hallucinations is frequently criticized. There have also been some unsettling exchanges.

HeyLibby is exclusively intended to respond to queries about the products and services offered by the company.

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

The company allows business owners to alter the queries and responses of the bot. Every time the bot engages with a consumer, they are informed and given full details about the interaction.

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

Rascoff anticipates that all small firms will employ AI in some capacity when speaking with potential customers.

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

HeyLibby, which is short for “link in bio,” intends to make money by providing upscale add-ons and services.

Rascoff noted that while there are several chatbots in use by businesses for their own customer service requirements, heyLibby is distinctive in that it focuses on SMBs.

Rodriguez stated that although the business currently uses OpenAI’s API, it may eventually create its own substantial language model.

For more than four years, Rodriguez oversaw teams at Zillow that handled the management of external services like Salesforce and Zendesk. After leaving Avalara, she eventually joined Slalom, and just before heyLibby, she was a director there.

Small worked for Zillow for more than eight years, managing the company’s primary Premier Agent division, which aids realtors in lead generation and advertising on the real estate site. Prior to working at Zillow, he spent five years at Amazon and held the positions of chief revenue officer at Convoy, Pro.com, and Wiliot.


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