How Square Root Takes an Empathetic Approach to Customer Success

by Keith Reid-Cleveland
December 30, 2019
Guilllermo Leon
Square Root

Seven years ago, Guillermo Leon joined Square Root as the founding member of the customer success team. Motivated by a belief that authentic connections would lead to lasting relationships and inspired products, Guillermo set out to build his own brand of customer success.

In 2013, Square Root wove Guillermo’s philosophy into one of their core values, “be customer inspired,” which encourages empathy, innovation and results. Guillermo said he nurtures his growing customer success team through this lens. 

Today, Square Root leans on a collaborative process, technical expertise and its store operations platform,  CoEFFICIENT®, to curate data for clients so they can make informed decisions. Of course, at the helm of that expertise is the customer success team. 

We caught up with Guillermo to learn how he and his team strive to be “the best partner their clients have ever worked with.”  

Looking back to when you first joined Square Root, what attracted you to the company?

At that point in my career, I wanted to drive the strategy and direction of a company and also redefine the field of customer success based on my experience in the area. As a bootstrapped company, I knew Square Root would push me to be a better operator, to think creatively and to be resourceful. Our product supports Fortune 500 companies with a novel approach to field management. I wanted to be part of paving a new path and defining a new domain. 

And lastly, but certainly not least, the people, their drive and work ethic were a significant factor. In the past, I worked with Chris Taylor, our CEO, and a handful of other folks. I respected the team, admired Chris’s fair, but firm, approach, and seven years later, I’m still excited to take on the challenges ahead of us, together.  


Who are Square Root’s customers?  What’s important to keep in mind when building relationships with them? 

Square Root has customers in the auto and retail industries, which include Nissan, VW, Subaru, Mazda and Walgreens. We adapt our high-touch approaches to each customer in order to support their individual style and business goals. This takes empathy and curiosity about other people. I strongly believe that people buy from people they like, so we always exceed customer expectations, deliver measurable business value and invest in building relationships with our business owners. 

Connecting to the individuals allows us to understand them, their motivations and how the collective team fits into their company’s dynamic. From there, we’re able to analyze problems, show and develop expertise in their domain, present creative solutions and build trust. I strive to make Square Root the best partner our clients have ever worked with, which is absolutely a point of differentiation for us. 

I strongly believe that people buy from people they like, so we always exceed customer expectations.”


Why do you think this approach is successful?

Having a partner you trust and that cares about you, as well as your career, is rare. Folks are keen to hold onto that. On average, our business owners move positions every two years, and when they move on, we keep tabs on our ability to re-engage with them. We’re brought into new areas of business within the same client or with new clients by individuals who know the value, strategy and expertise our customer success managers bring. 


How do you inspire your team to adopt this same methodology and practice?

I seek folks who believe in and want to learn our brand of customer success. Being authentic is the key to building true connections, so I bring my full self to work each day. I foster a jovial, caring and inclusive environment. I encourage my team to speak freely in our meetings. I advocate for their perspectives, so my team has a voice about all things Square Root, including our product. 

We also travel a lot, so to make it fun, we have a tray-table challenge within my team. The goal is to bring the wackiest (but safe!) item onto the plane. Recently, one of our data analysts, Michael, brought his AeroPress with coffee grounds, a scale to weigh water and a mug to make coffee mid-flight. 

Our team is light-hearted, smart, energetic and open-minded. This mindset permeates outward to our customers; they want us as their partner for our ability to deliver value and because they enjoy working with us. 


How do you and Square Root support career growth for members on your team?

As a small company, we hire generalists excited to have an impact and wear multiple hats, including project management, account development, sales support and product training. As individuals try on different hats, they learn more about their strengths and motivators, which helps me guide them to a specialty. We’re also known to craft roles for the individual, making career growth deeply personalized. On that same note, Square Root offers $3,000 a year for every individual to “learn anything.” Our philosophy on learning and growth is to let the individual direct their own path with support from the leadership team. 

What unique qualities or experience do you look for when bringing on new members to your team?

In general, at Square Root, we hire employees who bring gumption, curiosity and creativity to their roles. There’s no playbook, so we want folks asking questions and seeking to learn and improve upon their past experiences. In customer success, we embed ourselves with our clients, so craving knowledge and impact is crucial for us. Tactically, having experience with software development serves you well in any role at Square Root, as well as empathy. We want folks to truly embody our value “be customer inspired” by caring about the unique challenges of our stakeholders and users.  

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