HeyLibby logo on a computer screen
Illustration by Lanette Behiry/Real Estate News

Former Zillow CEO unveils latest venture: an AI-powered, lead-gen assistant 

Serial entrepreneur Spencer Rascoff predicts real estate agents will be “one of the biggest verticals” that will use HeyLibby to turn contacts into customers.

August 18, 2023
2 minutes

Key points:

  • The HeyLibby chatbot tool is designed to help small business owners field and vet qualified leads.
  • HeyLibby is currently free but will eventually add paid, premium features.
  • Partners Tony Small and Anna Rodriguez previously worked with Rascoff on the lucrative Zillow Premier Agent platform.

Spencer Rascoff, whose many titles include former CEO of Zillow and co-founder of luxury home co-ownership startup Pacaso, has unveiled his newest venture. This week, the serial entrepreneur, along with partners — and former Zillow colleagues — Tony Small and Anna Rodriguez, launched AI-powered assistant HeyLibby

Spencer Rascoff

Here's how it works: A user's "Libby" is a chatbot tool that can field inquiries, communicate with prospects, and even schedule appointments for a small business owner, the partners told Real Estate News. The idea is that the Libby assistant responds immediately in hopes of converting a prospect into a lead.

The product is aimed at sole proprietors, such as real estate agents, salon owners or photographers, who may be busy and unable to respond to an inquiry right away. The service, which is currently free, generates a HeyLibby Link customers click on to start a conversation and answer questions, which can be customized.

"It creates a way for a small business that's active on social media to engage with their followers and turn their social media presence into a qualified lead and an appointment," Rascoff said. "We absolutely think that real estate agents will be one of the biggest verticals that end up using HeyLibby because a real estate agent that's active on social is going to want to have an AI bot that answers a lot of qualifying questions."

Rascoff also flexed partners Small and Rodriguez's background and work at Zillow on the lucrative Zillow Premier Agent product

At Zillow, "we took one of the biggest verticals of small businesses and created the biggest ad product for them," Rascoff said. "About $2 billion a year is spent by real estate agents buying leads from Zillow. … Tony and Anna are sort of being humble describing their backgrounds but they built that business."

HeyLibby has a "freemium" business model, with a free version of the product that will eventually include premium, paid features, Rascoff said.

"But one of our core values behind it and our thoughts is we want small businesses to be able to grow and grow," Rodriguez added.

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