Jessica Bouthillier and Courtney Branson, the VPs of Operations and Culture, respectively, share their intertwined journey to leadership

Usually when people ascend in their careers, they tout things like ambition, assertiveness, and dedication as the keys to success and growth. Rarely is motherhood mentioned. In fact, it is often something that is omitted or glossed over in the professional realm because of the stigma surrounding being a working mom who often has to deal with frustrating questions such as, “how do you do it all? Surely there is something taking second place?”

Courtney and Jessica started at Square Root only a few months apart, seven years ago. Courtney joined the Square Root team as HR Manager and has since transitioned to a more culture-focused role, bringing Square Root to the forefront of culture and inclusion in the workplace. Jessica began her time at Square Root as a Customer Success Manager and is now the heart of operations. At that time, Square Root looked a lot different than it does now. 

“There wasn’t a pumping room when I first started,” said Jessica. “There had only been one other new mom [at Square Root].”

Inspired by working moms in her life, Courtney added parental and caretaker leave programs in her first year. In addition to flexibility + paid leave for new parents, Square Root’s offices offer a comfortable space for pumping and breastfeeding, earning them a designation as a Texas Mother-Friendly Worksite. More than that, Square Root went through a cultural transformation during this time, encouraging employees to bring their whole selves to work.  

In her first quarter, Courtney wanted to craft an intentional hiring process, but she didn’t have recruiting experience. The first open role was Customer Success Manager, Jessica’s role at the time. Courtney leaned on Jessica to understand the nuances + characteristics of the role. Together, they filled the open role. Since then, they built a friendship and collaborative style to amplify each other’s voices at Square Root.

“We use each other as sounding boards to discuss our ideas before a big meeting,” said Jessica.

Both new to Austin when they met, Courtney and Jessica embarked on new adventures in motherhood when they welcomed their daughters, Henley and Lisette, hours apart.

“Being a mother has helped me be a good leader,” said Jessica. “It’s inherent to me now to care about other people, and helps you to be a great multitasker and learn how to prioritize.”

Courtney agrees, adding that motherhood has increased her compassion for others. 

“Leaders should open doors for people. I learned that as a parent,” said Courtney. “My daughter wants to be an artist so I filled her room with art supplies. How can I do the equivalent for my team?”


"Courtney and Jessica have been my partners in shaping Square Root's culture-driven, collaborative workplace over the last seven years. It's been rewarding for me to see Courtney and Jessie grow as leaders and mothers throughout the past seven years, and I'm looking forward to what we can build together in the future."

Chris Taylor, Founder + CEO

Since stepping into a more culture-forward role, Courtney has helped elevate and embody many of Square Root’s own values, such as Thrive, which celebrates authenticity in the workplace — and it goes far beyond simply having a casual dress code. From establishing Square Roots (SR’s charitable giving initiative), creating the Learn Anything program (which helped land us in People Magazine), and leading her own team — appropriately dubbed the Tamers of Chaos — Courtney has demonstrated that empathy, inclusion, and diversity are not just buzzwords at Square Root. A true visionary, Courtney has challenged and dismantled many negative commonalities of a typical workplace, curating her own, award-winning brand of company culture in the process.

As the operational heart of the company, Jessica coordinates and plans all of the contracted work across teams. In addition to that, she keeps the organization in the loop on goal-setting processes during weekly Monday kick-offs and Friday check-ins. Despite the various role changes throughout the years, Jessica has managed to build a customer-inspired team, nurturing them in such a way that she was able to fit into this new role without sacrificing the customer experience. Part of her integrative approach to leadership is her penchant for mentoring junior Radicals (employee moniker) and nurturing the next generation of talent.  Jessica embodies the Be Customer Inspired value and inspires others to do the same. 

Courtney and Jessica, not only add their unique voices to the mix, but they show that motherhood, and the empathetic approach it nurtures, has a place in leadership.

About Square Root

Founded in 2006, Square Root develops data curation software for automotive OEMs to empower field and dealer leadership. Their software and data as a service platform, CoEFFICIENT®, blends data science and collaborative workflows to turn disparate data into actionable insights. Square Root supports over half of the major OEMs and partners with software providers for most U.S. dealers. Square Root has received accolades for its culture in local and national press, including Fast Company, Fortune, and Inc. magazines. Follow their journey at