by Sarah Williams

Originally published on May 10, 2022 on PowerToFly

Dileshni Jayasinghe grew up swimming around the beautiful islands of her home in Sri Lanka.

From a young age, she actively pursued what she loved and dedicated herself to mastering new skills, even if they scared her. As a kid, this led her to learn to scuba dive and swim competitively. As an adult, she plunged into learning how to code from scratch and pursuing a career in software engineering, despite having grown up without a computer.

We sat down with Dileshni to hear more about her experiences, her work as a Senior Engineering Manager at PagerDuty, and her insightful advice for increasing diversity in tech.

Determination is Key for Growth

Dileshni’s family moved to Toronto, Canada during her last year of high school. While dealing with the challenge of a new culture and country, Dileshni was thrown into her first computer courses — Java and visual basics — with very little computer experience. “I liked it because it was challenging and it wasn’t something I had done before,” she explains. Though she struggled to keep up with the rest of her class, she enjoyed the challenge enough to pursueComputer Science as her college major the following year.

“I felt like it was this puzzle that you can solve and you can do so many cool things with it,” says Dileshni. She did a lot of her learning at university, which she admits was extremely hard, since she had to play catch up. “The first two years I thought about dropping out,” she says. “I wasn’t at the same level as the other kids who grew up learning computer science overnight.”

Through hard work and perseverance, Dileshni learned to give herself the grace to learn at her own pace. “My stubborn streak came out and I said, ‘No, I started this, I want to finish it,’' she says. “And I [ended up] developing really good habits about learning new things and giving myself space to learn on my own.”

Her determination opened the door to dive straight into her career. After gaining ten years of software engineering experience, she was offered an opportunity at PagerDuty, a multi-product platform that helps companies of all sizes proactively manage their digital operations. What first attracted her to the company was the people, who she deemed as inclusive and empathetic. That, along with the opportunity to develop her skills on a deeper level, convinced her to accept the offer.

Stretching Her Skills at PagerDuty

Another thing about PagerDuty that stood out to Dileshni was the opportunity for growth and development. “PagerDuty really encourages me to grow and gives me opportunities to stretch my skills and keep growing in my career” she elaborates. “At other companies, I felt like I had to ask for opportunities and always push to learn something new.” At PagerDuty, she has been learning and growing from day one.

For example, one of her managers offered her the chance to manage a second team of engineers in the Event Management group. “I still remember thinking, ‘Are you sure this is a good idea?,’” she reminisces. “But he believed in me and he gave me this stretch goal and I surprised myself!” After successfully leading multiple teams, she was asked to lead the PagerDuty Process Automation (formerly Rundeck) teams. This was a bigger challenge, because it involved taking on a team from a group recently acquired by the company.

“My manager told me, ‘You're going to have to grow this team, launch a new product, learn how to work with a whole different set of people who are coming from a startup world,;” explains Dileshni. “I thought, ‘Well this is a big challenge, but I'll give it a shot.”

As a woman and person of color, Dileshni emphasizes PagerDuty’s work in creating places “that foster inclusion, well-being, and innovation,” which enables safe spaces to ask questions and have the resources to step into new challenges.

“PagerDuty is a place where people really like to help each other and see each other grow. All my coworkers are people who would say, ‘I'm not sure about this either, but let's work on it together and we'll figure this out.’”

Finding Ways to Support Your Peers

PagerDuty enables a strong community by providing learning and development programs, gender pay equity, generous paid parental leave, and employee resource groups (ERGs).

One of the ERGs is SisterDuty, a group of women, non-binary, agender, genderqueer, and ally Dutonians who regularly get together and give back to the community. PagerDuty also partners with local organizations that provide education for women and non-binary people in tech.

Apart from her strong community at work, Dileshni credits her confidence as a woman in tech to her group of mentors, women who cheered her on when she came back into the workforce after becoming a mother. Much of this support has led her to create initiatives that help bring visibility to women and people of color in tech.

One of these initiatives was a volunteer-based tech talk development platform for diverse professionals. When she spoke to tech event organizers, she noticed the speakers weren’t reflective of Toronto’s true tech community. “We wanted to see more people like us speaking at tech conferences,” explains Dileshni. “So I said, ‘Why don't we start something where we give people a welcoming space to do their first tech talk?”

Over five years, Dileshni and a group of volunteers supported countless women and people of color by giving them a space to practice their tech talks, receive feedback and training, and connect them to monthly events. She hopes to continue making an impact in the tech space by giving diverse professionals in tech new opportunities to grow in their careers and communities.

How to Bring Diversity to Your Team

“Diversity in tech is important because you get so many different perspectives from people,” says Dileshni. “If you have a diverse group that you're working with, you see how their careers are growing, and it gives you a vision for your own future.”

We asked Dileshni for three pieces of advice in creating places of diversity in the tech field:

1. Listen to your team. Diverse perspectives are important. “Don’t just hire people from different backgrounds, but give them the space to share their ideas and feedback,” advises Dileshni. She recommends keeping it personal. “I prefer one-on-one conversations, not surveys. You have to find unique ways to communicate, ways that make sense for your team.”

2. Be aware of your own bias. “We all have different biases, right? If you're lucky, someone will point it out,” she says. “You should thank them for it because it takes a lot of courage for someone to share that with you.” Being aware of your biases allows you to see how they affect people, and what work you can do to address them. “They're not sharing it as a negative thing. It's because they want you to understand that bias and how it might be affecting them,” Dileshni continues. “Communicating and setting expectations with your team is important. Let them know that it's okay for them to come to you about these things and give you feedback.”

3. Create equity within your company and your team. “Managers have the ability to push for pay and promotion equity, and recognize the work that underrepresented folks do to hold teams together,” says Dileshni. “Recognize the work they do to create inclusive places of work and always look for ways to improve the work culture.”