Engineering joy

“Happiness is something that happens to you, but joy is a choice you make every day,” believes Jayashree Sundaresan, who joined Freshworks in January as senior director of engineering.

Today, Jayashree and her team are working on building AI-enabled features in our IT service management (ITSM) products—from self-service to copilot assistance for finishing tasks to providing insights for top decision-making. Though in some sense revolutionary, it’s also unsurprising for someone who, more than two decades ago, was all too aware of “making heads turn” as a 17-year-old engineering student in a predominantly male class.

What’s the secret that enabled Jayashree to rise up to become an exemplary engineering leader first at PayPal (where she spent 16 years) and now at Freshworks?

It’s a story she recounts with—what else?—loads of joy.

When Jayashree made the choice to join Freshworks, she wasn’t looking for just “any other job.” As she interviewed for the position, she found everyone at Freshworks to be “warm, knowledgeable, and authentic.” Recalling those moments, she says, “I knew right away that this was it!”

From playful moments to a career in engineering

Jayashree vividly recalls her first brush with engineering as a spirited 6-year-old: “I used to play with construction workers’ tools on summer holidays in the sweltering heat of Chennai—much to my mother’s surprise!” She was fascinated with the idea of building something from the ground up with whatever tools she could lay her hands on.

From that moment, she knew she was going to be an engineer one day, although it was much later that the difference between civil and software engineering became clearer to her. When the programming bug bit, crafting all kinds of code—whether a simple “Hello, world” or bringing the Fibonacci sequence to life—filled her with a sense of joy and accomplishment.

Talking about her college days and the experience of being one of the few female students in engineering, Jayashree says, “Technology was commonly considered a man's domain, while humanities were considered more suitable for women. That was the prevailing mindset.” 

Thankfully for Jayashree, the support of her parents and her own fearless nature helped her cope well and set her up for future success. After completing her engineering degree in electronics and communication from the University of Madras, she took a job in Chennai and then moved to the U.S. in 2001. In her own words, she was “destined to become the first female engineer” in the family.

Choosing to become a people manager

In 2006, Jayashree joined PayPal as a tech lead. After a decade of being an engineer, however, she realized she derived much more joy (that little word again!) from helping others succeed than from her own success. “That’s when I decided to become a people leader,” she says. She also signed up for an MBA from Santa Clara University while transitioning into a people-centric role.

Somewhere along the line, Chennai came calling again and this “hardcore Chennaite” moved home to the Indian city in 2011, continuing at PayPal for another decade.

In her current role leading a team of 90 across ITSM at Freshworks, what excites Jayashree the most is the “freedom to step up, take ownership, and run with initiatives.” She is also quick to add that the “happy work environment” makes it easy. (Editor’s note: Happy work environment is part of CHAT, the Freshworks culture code.)

Jayashree (in green) collaborating with her team.

Jayashree is equally excited about Freshworks “making waves in the enterprise segment,” in addition to serving smaller businesses. “To keep the momentum going, my focus leading ITSM engineering at Freshworks is on investing in product maturity so we continue to hit the sweet spot for larger customers while maintaining the simplicity of our tools for mid-market customers,” she says. 

That is easier said than done, of course. Jayashree has to do a “dynamic juggling act,” with unlearning as important as learning. “My work as a leader is all about building the product we envision, meeting the expectations set by leadership, ensuring clarity for my direct reports, and nurturing a supportive environment for my entire team.”

Collaboration is another important aspect of her work. To get it right and “keep the ship moving,” Jayashree advocates lateral measures such as “moving the water around it” and “creating a safe space for her team to speak up.” As a leader, she champions building solid relationships based on empathy and compassion so that her team feels comfortable taking risks—because that’s the only way innovation can happen. “In a sense, leadership is just like being a parent,” she says.

Advice she often gives her team is to be fearless and approach everything with genuine curiosity. “What is the worst that can happen?” she says. Her mantra is simple: “I firmly believe in the journey of learning and embracing the opportunity to grow, even if it means making mistakes along the way.”

When she’s not at work, Jayashree spends her time volunteering with the Shooting Stars Foundation and other NGOs, participating in beach clean-ups and tree-planting campaigns, painting school walls, sharing inspiring stories with children, organizing sports activities in her community, and raising funds for the disadvantaged. “Our time on earth is a gift that is meant to be spent spreading positivity and joy,” she says.

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