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AI and the Self-Care Client Experience: Embracing the Possibilities

By Sean Stavropoulos, Co-Founder & CTO at Boulevard . Jul.17.2025

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Boulevard today officially announced that it has raised $80M in Series D funding. This latest round comes nearly 10 years after my co-founder, Matt, and I stumbled upon a problem that we just had to get to the bottom of: why was it so hard to book a haircut online? As Matt describes in his own blog this morning, it’s been an incredible journey for us as founders, Boulevard as a company, and the entire self-care industry.

The funding comes at a transformational time, not just for our business and our industry, but for software specifically, technology in general, and, frankly, for the entire world. I’m, of course, talking about the impact of AI. As Boulevard’s CTO, I’ve been thinking a lot about AI lately; about what it means, where it’s going, and how Boulevard fits in.

To understand how we think about AI at Boulevard, you have to go back to the beginning, back to that problem we just had to solve. Believe it or not, there were other online booking platforms before Boulevard, but salons and spas refused to use them (even after they’d paid for them). Why? Because they couldn’t replace front desk staff who had mastered the art of stacking staff calendars.

Knowing that time is money and gaps in the daily schedule are deadly to the business, a receptionist booking an appointment, either over the phone or in person, would take great care to optimize the daily schedule with tricks like clustered appointments, double-booked services, and short appointments to fill stray pockets. While the earliest booking platforms could minimize the need for manual labor and move much faster than a human could, they couldn’t think like one. They’d leave salons with scattered start times and large, costly gaps in the daily schedule.  

Our initial challenge with Boulevard was to come up with a way to build an online booking platform that combined the speed and power of a software solution with the smarts of a human. Our answer was something we called Precision Scheduling. Still one of our most popular features to this day, Precision Scheduling leverages a proprietary, machine learning algorithm to analyze booking patterns, appointment durations, and provider availability to suggest the most efficient appointment times.

Now, if that sounds a lot like what people think of today as AI, well, that’s because it is. Thus, in many ways, the story of AI at Boulevard is as old as Boulevard itself. In the years since, we’ve continued to leverage AI and other intelligent technologies where and when it makes sense for our customers, with features such as our marketing suite and popular chatbot Billie utilizing AI to make life easier for our customers and their clients.

I just used the phrase “where and when it makes sense for our customers,” and that was no accident. When and where it makes sense for our customers isn’t just a phrase; it’s our North Star at Boulevard. You’re not going to see us overuse and abuse the term AI, chase headlines with it, or otherwise build AI capabilities for the mere sake of it. What you will see is what you’ve always seen from Boulevard: a commitment to exploring any and all avenues to making our customers successful.

Here's the thing, though: a great many of those avenues already lead to AI, and even more will in the future as AI capabilities become even more powerful and precise. AI holds enormous promise for the self-care industry. Whether you’re talking about using it to deliver smarter, more customized recommendations for clients, fine-tune your menu of services and optimize marketing and communications, or develop the most effective packages, promotions, and membership programs possible, AI is poised to help self-care businesses grow revenue, create more personalized experiences, and achieve greater operational excellence. And with our Series D secured, Boulevard is ready and eager to lead the way.

I recently heard someone compare the new era of AI-driven business and technology to driving on ice. When you feel your car starting to skid, your instinct is to slam on the brakes and steer in the other direction, when, in fact, the only way to regain control is to turn into the skid; to embrace it, so to speak. The same is true of AI. When it suddenly feels like AI is everywhere, the best – the only – thing you can do is embrace it. At Boulevard, we couldn’t be more excited to embrace the possibilities that AI holds.

Where and when it makes sense for our customers, of course.

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