AI assistant startup heyLibby finds traction with gyms and tanning salons, raises $4.5M

heyLibby, a Seattle startup that helps small businesses in the health and wellness sector use AI to answer customer inquiries, raised $4.5 million in a seed round led by French firm Aglae Ventures and Silicon Valley-based Vertical Venture Partners. What heyLibby does: The company, which we first covered in 2023, sells AI assistant software that can handle phone calls, emails, chats, and texts — both inbound messages that come from customers, and also proactive marketing out to customers. The idea is to help gyms, recreational facilities, yoga studios, and other wellness businesses improve customer service and free up staff to… Read More

Apr 2, 2025 - 15:54

AI assistant startup heyLibby finds traction with gyms and tanning salons, raises $4.5M

heyLIbby co-founders Anna Rodriguez (left) and Tony Small. (heyLibby Photos)

heyLibby, a Seattle startup that helps small businesses in the health and wellness sector use AI to answer customer inquiries, raised $4.5 million in a seed round led by French firm Aglae Ventures and Silicon Valley-based Vertical Venture Partners.

What heyLibby does: The company, which we first covered in 2023, sells AI assistant software that can handle phone calls, emails, chats, and texts — both inbound messages that come from customers, and also proactive marketing out to customers. The idea is to help gyms, recreational facilities, yoga studios, and other wellness businesses improve customer service and free up staff to focus on other tasks.

heyLibby spent the past two years figuring out product-market fit, eventually landing on health and wellness. “These businesses get calls and emails all the time — and they just really need help answering them,” said CEO Tony Small.

Customers: Arena Sports, Seattle Sun Tan, Desert Sun Tanning Salon. Arena Sports is able to automate about 70% of its communications with heyLibby’s software, Small said. heyLibby serves the U.S., and plans to expand to Western Europe and Canada soon.

Match Group CEO Spencer Rascoff co-founded heyLibby. (Match Group Photo)

Revenue: More than $200,000 in annual recurring revenue.

Competition: Zenoti, another Seattle-area software company, also targets the wellness sector and has its own AI assistant. There are a number of other startups building AI assistants.

Founders: Small and his former Zillow Group colleague Anna Rodriguez co-founded heyLibby, alongside former Zillow CEO Spencer Rascoff, who is now CEO at Match Group.

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 launching 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.

Other details:

heyLibby also sells a white-label product used by businesses that want to offer AI assistant services. Small said that more than half of the company’s revenue comes from selling to other businesses.
The 3-person startup uses an array of back-end AI infrastructure, including ChatGPT and ElevenLabs, to power its services.
Rascoff, who is an investor in heyLibby, said the health and wellness sector is a “huge category with high customer service needs and a front-desk workforce frequently distracted with multiple tasks.” He added: “This is a perfect customer base for an AI sales assistant.”