Of the many factors that drew Richa Gupta to Castlight Health, its connection to a broader purpose was chief among them.
Castlight is a healthcare navigation company that connects hundreds of health vendors, benefits resources and plan designs on one health and wellbeing platform. It has leaned significantly into its purpose over the last year, pivoting to build out a COVID test-site finder and managing the backend of the CDC and Boston Children’s Hospital’s vaccines.gov effort.
As chief people officer, Gupta is striving to ensure all employees are inspired by and aligned to Castlight’s purpose. To that end, she says, she was heartened when the executive team recently unveiled a fundraiser with a company match to provide support for communities hard-hit by COVID-19 in India; within four hours of announcing the initiative on a company all-hands call, employees had already helped the organization meet its fundraising goal.
“What I admire so much about Castlight’s culture is that it’s so centered on communities, care, belief in a mission, collaboration and innovation,” Gupta says. “And the last year brought the best of our culture forward.”
Gupta—a former HR leader at PayPal, GE Digital, Vantiv and LexisNexis, among other organizations—shared how she hopes to build upon that culture moving forward.
HRE: You’ve led HR at start-ups, global companies, organizations going through a transformation—what has been one common HR lesson that has helped you find success in all of those settings?
Gupta: I would say HR being a part of the business strategy, not a standalone. It’s always inspiring to understand what’s going on in the industry your company is in and with the company leaders—listening and asking questions, understanding the background, contextualizing HR and being that galvanizing force to pull everybody together to find the right outcomes. That has been at the highest level of lessons I have learned in my career.
HRE: What attracted you to Castlight?
Gupta: I took a short sabbatical between PayPal and Castlight. When I left PayPal, there was this extreme desire to really understand what my second act needed to look like. I did take four to five months and reflected on it a lot. I was very clear in my criteria—there were three things. First was the shared purpose of the company. What was the company setting up to do in addition to making money? How is it aiming to make a greater impact in the community? Second was the culture. Working in large companies, you get used to different cultures and dynamics, and I wanted to go to a place that had less ego and big ambitions and people really behind the mission—a strong culture where people have each other’s backs, are in it together, own each other’s productivity. And the third piece was [I wanted] a role that gave me a bigger, better opportunity to make an impact. We [at Castlight] are market leaders in navigation and are taking the company to next level … to help employees, users and their families navigate to the right care at the right time. What would be a better time than COVID to ensure healthcare strategies are becoming the core of a company’s workforce strategy?
HRE: What was the experience of onboarding during the pandemic?
Gupta:It has been unique and interesting but a great onboarding experience. Digital onboarding has been tough because there’s no replacement of meeting people face to face, getting into those deeper, in-person conversations. All of that accelerates trust that is so critical to my work. But, you know what? All of us are in it together and this experience has given me and other executives a new perspective, wiser compassion, deeper empathy into what our employees and their families are experiencing. We always talked about this whole person sentiment, but through this time, that concept has become really clear. As I’ve been onboarding, being in the same situation, working remotely like many of our employees and our executives, has given me a great sense of the opportunities and challenges that lie ahead and has really opened my eyes.
HRE: What is your immediate HR priority, and how do you see that shifting over the coming months?
Gupta: This is my first time in healthcare, and what an amazing time being in healthcare. So, [initially] it was a lot about learning our industry, learning our products, learning our customers and executive teams, and supporting our workforce that was in the thick of remote work. There was a lot of employee experience-oriented work in the first four to five months, and that’s still continuing. Our current priority is all about the return to work. We are looking at a mid-summer window to start that transition. There’s been a lot of planning—tactical and logistical—and communication to employees. And, in the midterm, the shift is going to be around how do we help the business learn the new ways of working? How do we reimagine how we can work differently? How can we accelerate productivity differently? How can we grow employees differently?
HRE: How do you think the pandemic has reshaped the employer-employee relationship?
Gupta: Throughout this time, employees learned to trust their employers more than they trust media or government. They’ve relied on employers for support, knowledge and resources. That’s one shift that has occurred. The second is all about vaccinations. We do a lot of research with our customers—many large to midsize employers—and many are making vaccines available either on site or in near-site clinics. There’s also been a lot of work around vaccine literacy. We have a lot of opportunity here to impact the sustained wellbeing and healthcare of our employees more closely. I think healthcare has become the core of the workforce strategy, and I truly believe it’s the new frontier for all things diversity and inclusion. Employers are being pushed to understand their employees in a way they never had the opportunity to—or took the opportunity to. By understanding who they have, they’re tailoring healthcare and benefits strategies around that and then offering solutions for sustained wellbeing, all of which is a big shift in the relationship between employers and employees.
HRE: What “soft” skills of your own have helped you lead HR through such a difficult time for both employees and organizations?
Gupta: The ability to create trust quickly and learn quickly, with a lot of humility. I joined Castlight, in a new industry, in the midst of all of this. I was not with people so the way I learned had to be pivoted. I would also say horizontal leadership and galvanizing skills—bringing people together even when COVID was hitting and remote work and connections were hard. Also, comfort with ambiguity and a lot of courage—the fearlessness of saying, “Nobody has a playbook for this; I don’t either.” First, it’s acknowledging that and then having the courage to not only lead myself and my function through it but also the leadership team—to reimagine what the future needs to look like and how do we push forward.
HRE: If you hadn’t gone into HR, where do you think your career would have taken you?
Gupta: I think there would have been potentially two paths: either teaching somewhere—I really like education, both of my parents were professors—or I would have been a doctor. I was so passionate, even as a child, about healthcare.
HRE: What would co-workers be surprised to learn about you?
Gupta: There are many things. But I think one fun fact could be that I came to the U.S. 22 years ago with $4,000 and a suitcase. And that was the beginning of life. There’s been lots of learning, lots of growth, lots of success and lots of failure. And I’m still on a learning journey.
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