Meet Castlight: Q&A with Richa Gupta, Chief People Officer

In our new 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 Richa Gupta, our Chief People Officer.

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

My role as chief people officer at Castlight is to collaborate with the leadership team and all other Castlighters to nurture “all things talent” and help create a culture where our workforce thrives, our teams deliver value to the customers, and we fulfill our shared purpose of enabling happier, healthier, and more productive lives.

The better we care for and support Castlighters, the better they can assist our customers, their employees, and employees’ families in navigating the healthcare system and their own personal health journeys.

What led to your decision to join the Castlight team?

Coming out of a short career sabbatical after my role at PayPal, a deeply purpose-driven company, I was ready for a company with a deep mission and a compassionate and values-driven culture, a company undergoing transformation in an industry ripe for disruption, a company where I could play an impactful role with uniquely talented colleagues. It was a lot to ask for! As I explored Castlight, the company fared well in all these dimensions.

Moreover, this pandemic has left no doubt that the way employers care for and support the wellbeing of their workforce will determine their employer brand for years to come. Castlight’s vision of supporting all employees and their families so they can easily connect and engage with the right programs and care at the right time and be as healthy, happy, and productive as possible​ sits at the core of that purpose, and I am proud of our value proposition.

What’s your go-to mantra?

“Do not follow where the path may lead. Go instead where there is no path and leave a trail.” — Ralph Waldo Emerson

What is your go-to quarantine activity?

Living in California, we are blessed with beautiful terrains all around us. During quarantine, my husband and I have been enjoying long walks and hikes with our two teenage boys.

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

The main challenge for leadership with a remote workforce has been ensuring the seamless transition of the workforce to a remote environment while still maintaining traction on business transformations and growth.

The pandemic restrictions and incomprehensible COVID-related death toll are not the only brutal forces employers across the globe have battled with over the past year. 2020 surfaced numerous tectonic shifts — a need for a more just world, unemployment rates rivaling those of the Depression era, unwinding economies, a need for more innovation in every walk of life, historic civil and political unrest, and more.

We are navigating a climate in which people lean on their employers more than government authorities in order to be heard, understood, and supported. The role of the employer changed in meaningful ways, and leaders had to learn (or unlearn) how to listen, connect, and mobilize their workforces. “Wise compassion” — getting tough things done in a human way — has been one of the skills leaders had to master fast. It was an opportunity to learn how to balance concern for their people with the need to move their organization forward in an efficient, productive manner that delivers results.

A strong culture and sense of camaraderie at Castlight was an asset to our transitions and overall success. Amongst many strategies we established to help lead in the new normal, unlocking our front line and middle management to maintain traction on productivity and employee care has been key for us in this complex time.

In summary, it has been an incredible year in terms of how Castlight pivoted to deliver on the need of the moment. COVID-19 presented us with challenges, and we had to make tough calls as a business. The entire team showed up for each other during this difficult time; we stuck together as one team and demonstrated creativity and innovation in our response to COVID-19 both internally and with our customers.

What are you most excited about as the next innovation in digital health?

For me, it’s the trend of “digital when you want it, human when you need it.” High-touch healthcare solutions — like Castlight Care Guides, our team of benefits and clinical experts — enabled by the digital transformation of the healthcare ecosystem is the most exciting trend. Over the last two decades, I have witnessed the democratization of financial services, facilitating easier, more seamless access to all despite their socio economic status. This pandemic has accelerated similar fundamental shifts in this country’s sub-optimized healthcare system.

What are you passionate about outside of work?

I like reading and writing about topics related to HR, the role of HR as a product organization, talent, and leadership. My other equally important and fun mission in life is to raise my two sons (almost 13 and 16) to be grateful, growth-oriented, happy, and kind grown-ups. Yes…the world could use a bit more kindness!