October 7, 2021

Meet Castlight: Q&A with Ruby Dhaliwal, Head of Talent Management, Learning, and Inclusion

In our blog series, Meet Castlight, we’re featuring some of the best hearts and minds that drive our business. In this Q&A, we learn more about Ruby Dhaliwal, our Head of Talent Management, Learning, and Inclusion.

What’s your role? How does it support Castlight’s mission?

My role is to help create opportunities for all Castlighters to reach their fullest potential! As Castlight’s talent leader, I’m fortunate to be able to influence the way we build our people capabilities so we can continually deliver the best outcomes for our customers and the communities we serve. Enabling our customers to help their employees and their families lead happier, healthier, more productive lives requires us to collectively harness our strength from within through innovative talent practices that give everyone the opportunity to grow, thrive, and be their best and most true selves. Castlight employees’ deep enthusiasm for learning makes my role more exciting and allows me to introduce progressive learning and development approaches that can ultimately contribute to Castlight’s success.

What led to your decision to join Castlight?

After six years at my previous company, I was looking for a new adventure at a new place with a new perspective. Wanting to stay in technology, I sought an organization where the mission and values were aligned with my own purpose, where I could make an impact on the company’s people evolution, and where I could challenge myself in a way I haven’t done before. All of this led me to Castlight!

Also, it was significant for me to join a healthcare company during a global pandemic and to learn about the healthcare landscape from many different lenses. I am still amazed at the connectedness of Castlight’s culture. Our team members do not hesitate to lean in and help one another. It truly is One Team!

Why do you think diversity and inclusion is so important for companies, especially now?

To say this is the dawn of a new era is an understatement. The COVID-19 pandemic has magnified troubling health inequities, movements against social and racial injustice are setting precedents, and a new hybrid and remote work world has evolved the meaning of inclusion and belonging.

Today, a company’s brand hinges upon what they’re doing to make the world a better place. Younger generations have totally different perspectives on what the “employee experience” should be like. Due to this awakening, companies will now need to be more intentional about their internal and external actions and move diversity and inclusion from “nice to have” to a core component of their business strategy.

The degree to which a company is committed to a diverse and inclusive workplace is becoming a key component of a candidate’s decision to join, forcing companies to transform their hiring practices with a heightened focus on bias awareness and interviewing consistency. Employee Resource Groups (ERGs) are becoming resounding platforms of awareness and education and backed by senior executives to build a culture that invites every voice to be heard. And in a remote world, inclusive leadership is now seen as a non-negotiable skill that contributes to engagement, retention, and employee wellness and acceptance.

When it comes to diversity and inclusion at Castlight, what are your top goals right now? 

Castlight organically has an extremely diverse culture. For example, 51% of our U.S. workforce is made up of Castlighters who identify as women, with 40% in director positions and above. There’s much to be proud of but still a lot of good work to be done.

We’re in the midst of implementing new approaches to help us derive key insights about our diversity and inclusion landscape that can be translated into attainable goals. For example, we’re trying a new employee listening system that’ll enable us to gather robust data reflecting the sentiments of Castlighters across several diversity dimensions. Additionally, we’re planning to delve deeper into the diversity make-up of our business units in an effort to identify opportunities where we can further enhance our diverse hiring practices. From a cultural standpoint, we hope to increase our ERGs so we continually create a space for our rich diversity and equip Castlighters with the tools and empowerment to learn, share, and contribute.

What’s your mantra? 

“Carpe Diem! Make your lives extraordinary!”—the immortal words of Professor John Keating from Dead Poets Society, played by the late Robin Williams.

This quote has had a special meaning for me since my high school days. Oftentimes, many of us say to ourselves, “There must be more to life than this.” But it’s only when we believe we have the power to create the best for ourselves—and are willing to put in the work to get there—that we begin to make our own unique and extraordinary life. 

What’s the biggest challenge for leadership with a remote workforce? 

COVID has devastated and affected so many across the world, but it’s also shone a new light on the power of human connection and wellbeing and how important it is to be there for one another. We’re lucky to have access to technologies that enable us to stay connected and have devised many innovative ways to replicate in-person interactions. However, with the merging of work and home life becoming more apparent, opportunities remain to build skills that increase awareness of employee needs that extend beyond work.

To be successful in engaging and retaining their workforce in a remote environment, I believe leaders at all levels must practice empathetic leadership, which is about leaning in and understanding the context, experience, and needs of others and having awareness about how someone may be feeling. It’s about listening deeply and sincerely caring. As the post-pandemic world unfolds, employees expect their companies to respond to their needs authentically—or they’ll look for another company that can. Empathy has always been a crucial leadership skill and it is needed today more than ever to build a resilient and committed workforce that truly believes their company cares about them as a whole person.

What are you passionate about outside of work?

My passion is my family! If the pandemic has taught me anything, it’s how precious family is and how we should cherish every moment. Being a mum to a tenacious and vibrant three-year-old is a win of my “life career.” My husband and I are both Sikh, a religion that puts compassion, humility, and doing right by others at the core of who we are. So we are quite busy instilling these values in our son so he can see and welcome life from diverse lenses and put some kindness back into the world. This picture is from the Golden Temple in Amritsar, India, our last trip before the pandemic. In hindsight, it’s so memorable that we were there before the world changed, and that we have journeyed this far with a renewed will to look at life differently.

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