How going the extra mile to understand customers propelled Squire into a $750m SaaS company 

Barbershops are as American as baseball and apple pie. It’s also a line of business that hasn’t changed much in decades, observed Dave Salvant when he co-founded Squire. 

As a young man growing up in Brooklyn, NY, he would do odd jobs at a hair salon run by his aunt. As with any small business, he noticed she often had her hands full juggling duties. One minute she was styling hair; the next, she was answering the phone from customers calling to schedule a haircut.  

“Every few minutes she would have to pick up the phone and write in the appointments, and it really disrupted the flow for her clients,” Dave said in a fireside chat with ChurnZero CEO You Mon Tsang at the most recent BIG RYG conference.

Years later, Dave would go on to graduate college and land a job on Wall Street. His closely cropped hair would grow quickly, so he’d need to see a barber every other week or so. That’s when it occurred to him: the process of scheduling an appointment with the barber was the same as it was 20 years ago.

Dave had found his niche and Squire was born. 

A double-booking problem emerges 

Named for a character role in the Netflix series, Game of Thrones, Squire set out to be a reservation system for barbershops: “Open Table for barbers”, as some have put it. In a sense, it was originally more like a lead generation service, or marketplace for barbershops. 

Dave and his co-founder Songe LaRon cobbled together bootstrap funding and employed scrappy, guerilla marketing techniques – tagging key sites in New York City with a call to action to download the Squire app. But it didn’t go well. In Dave’s words, Squire was providing a “worse customer experience.”  

Why? While customers would book an appointment with Squire, the barber shops were still taking calls too, and would often wind up double-booked. The barbers still wanted cash payments too. So, while a customer might have scheduled a haircut through the Squire app on a mobile phone, they’d still have to stop somewhere to withdraw cash to pay for their haircut.

“We realized if we didn’t manage the full end-to-end solution, then it wouldn’t be a unique experience for both the customer, the barbershop owner and the manager,” Dave said. 

The company decided they had to build a more complete software product to be successful. Barbers needed a solution that was specifically designed for their business and that would improve the overall customer experience (CX).

A ‘bet-the-company’ gamble 

Six months after launching, one of Squire’s customers in Chelsea Market, a trendy shopping district in Manhattan, was going out of business. This presented a problem for Squire because that particular customer was piloting the more expansive solution they were building. Commercial rent is high in that location and this particular customer was losing money. When the business owner told Squire he was closing his shop, the company found itself in a hard spot. 

“We were like ‘no, no, no, we just spent the last three months building this software, you can’t’ [close the business]” said Dave. Such a closure threatened the progress they were making.

That’s when the team came up with a wild idea: Squire brokered a deal with an investor, Chelsea Market, and the owner to assume control of the barbershop. 

It was a huge gamble. On the one hand, the investment tied up Squire’s cash and put the company at risk of failing. On the other hand, owning a barbershop would serve as a customer research and development (R&D) laboratory. They would gain first-hand experience of what it’s like to be a barber. Such a deep level of detail isn’t possible to obtain simply from speaking to customers and prospects.   

“It’s one thing to get feedback, to solicit feedback, from customers,” noted Dave. “It’s another thing to do it yourself and actually be in the shoes and walk the walk that your customers are walking. I think that not only helped us design great software but also built a great rapport with our customers.”

The gamble paid off because the team realized the hardest part about running a barber shop is managing the people. 

“That was a real insight for us,” said Dave. “We wanted to make software that removed those frictional components and really let the entrepreneurs and the barbers focus on their passion, which is cutting hair, for the most part.”

5 lessons in customer success from Squire 

The fireside chat was full of lessons that customer success professionals can learn from. Below are some that stood out to us during the conversation.

1: Be ruthlessly focused on your ideal customer profile

It’s often tempting to look outside your ideal customer profile (ICP). Squire debated expanding its ICP to enterprise – think hair salon chains – hoping to scale faster. Yet that would fundamentally change the business, and perhaps waste what it had invested in R&D. They ultimately jettisoned the idea to stay focused on the market they knew. 

“I am going to focus on my customer because that allows you to design products and services that make sense for them,” noted Dave. “Don’t try to cast a wide net and horseshoe people into a product that is not necessarily built for them, because they’re going to churn anyway.”

2: Think about your customers’ customers 

The idea for Squire was born out of Dave’s personal frustration as a customer. He just wanted to find a way to get a haircut fast. Solving that problem was inherently valuable for barber shops because it was a problem for their customers. 

3: Walk a mile in your customer’s shoes 

Getting a haircut fast proved to be a different challenge than Squire initially thought. That’s because the CX was just one side of the equation. Being attuned to how its initial rollout affected the experience of barbers is what allowed them to make a slight pivot and seize an opportunity. 

Owning a barbershop enabled the team to understand all the frustrations their customers feel daily. That gave them the ability to empathize with their customers, which in turn helped them build rapport and credibility: Squire really understood the nuance of being a barber.

4: Get ahead of the problems

In a humorous twist with a powerful lesson, Dave shared – live on stage – that an angry customer was sending him direct messages as he was speaking. Squire’s customers are “noisy” and if they aren’t happy about the product, they aren’t shy about saying so out loud. 

“We try to get ahead of it,” Dave said. “We try to use technologies like ChurnZero to see if transaction rates are slowing down, to see if bookings are not what they used to be, so we can reach out to them before they get on the churn list.”

No company can make every customer happy all the time. More often than not, Dave said, customers just want to be heard – they want to know you know what they are going through.

5: Continuously show customers value

Barbers, like hairdressers and tattoo artists, tend to be “super passionate” about their profession. However, they don’t always think about the business aspects. 

That’s the opportunity for customer success at Squire – to show barbers how they can save money or earn more money with their passion by using technology. 

“It’s less about extracting dollars, and more about adding value because they view you as a partner and not somebody that’s trying to charge them for stuff,” he said. 

An overnight success… eight years in the making

It’s easy to look at a story like Squire’s and think they were an overnight success. Yet the fact is they’ve been in business since 2015 and didn’t get their first round of institutional funding – venture capital – until 2019. Even then, they were turned away from Y Combinator three times, and met with 150 investors that passed on their business, until they found one that offered a term sheet. 

Along the way, they’ve dealt with bias, worried about making payroll and faced significant challenges that would have given them a good excuse to just quit. And yet they didn’t. Instead, the constraints forced them to focus on the customer and build the product they needed. 

“The first thing I’ve learned on my journey is just don’t quit,” added Dave. “What they say is true: it’s darkest before dawn. I think a lot of people give up right before they’re going to make it.”

That’s perhaps the biggest lesson of all. Today, Squire has some 2,800 customers with an average contract value (ACV) of $12,000 and a valuation of $750 million. 

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The full fireside chat covered a lot more ground and is full of funny anecdotes. Watch it in full here. 

Featured image by Tim Mossholder on Unsplash.