Meet Castlight: Q&A with Holly DeLisi, Vice President of Pre-Sales Development

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 Holly DeLisi, vice president of Pre-Sales Development.

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

As a Pre-Sales leader, I’m always looking for better ways to enable and support Castlight’s Sales organization in targeting, positioning, and selling our best-in-class healthcare navigation solutions. Ultimately, we want to help prospective customers realize their vision, identify any roadblocks they’re encountering, and figure out how Castlight can best empower them to be wildly successful in helping their people be healthier, happier, and more productive.

What led to your decision to join the Castlight team? 

Fun fact: This is my second time working for Castlight! I first worked here from 2012 to 2018 before leaving to explore another opportunity for a few years. What brought me back to Castlight? Leadership —  leadership in the market, thought leadership in the industry, and company leadership. Castlight has a team of leaders who have been entrenched in the digital healthcare space, helped with some of our country’s healthcare policies, and created a strong culture of caring and innovation in the company.

What’s your mantra?

Be brave, be bold, but be kind.

What is your go-to quarantine activity?

I spent most of my quarantine with my close family — human and canine. I’m afraid to say that our two dogs, Cassidy and Trooper, were spoiled before 2020, and now I think every hour of the day revolves around them!


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

I’ve been working and managing remote teams for almost two decades now. The biggest thing is constant communication and making sure you bring people together (virtually) to build a true team environment.

While working remotely requires you to be self-sufficient, it does not translate into being a loner. Your team members need to feel comfortable reaching out to other people in order to be successful, and the best way to do that is to get to know each other on a personal level. Encourage them to call each other once in a while just to chat. You could also start team calls off with a minute of personal curiosity. Lead by doing — your team will take a cue from you.

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

Everyone’s individual health situation can change in a matter of seconds. With a platform like Castlight in your pocket (literally), you have a wealth of health and wellbeing knowledge at your fingertips, in addition to the ability to speak to a Castlight Care Guide — someone who knows about you, your benefits plans, and your health history. This is not only a relief, but a gift when you need it most. This type of platform will continue to be an absolute necessity in the ever-changing healthcare landscape.

As I look ahead, the innovation that comes out of this space will be specialized but limitless, and I’m excited about the opportunity to bring it all together under one digital home for health to make it easier for every consumer, regardless of their unique circumstances, to navigate their personal health journey.

What are you passionate about outside of work? 

I love to relax on the beach, I have a soft spot for almost any kind of animal, and I also drink lots of wine. Some day I’ll figure out how to combine all of that into the perfect hobby!