SalesTechStar Interview with Frank Jennings, SVP and Chief Sales Officer at Castlight Health

At a time when empathetic leadership is critical to overall business success, it is important for employers to pay attention to digital health needs of their staff as well; Frank Jennings, SVP and Chief Sales Officer at Castlight Health talks about this need while sharing a few pertinent B2B sales and salestech tips in this quick chat with SalesTechStar:



Hi Frank, we’d love to hear about your journey through the years…tell us about Castlight Health and more about your (new!) role here?

Castlight Health is a leader in healthcare navigation—we partner with Fortune 500 companies and health plans and provide a world-class digital platform and a team of clinical and benefits experts to help individuals easily connect and engage with the right care at the right time.

I’m thrilled to say this is my second time working at Castlight; I also worked here from 2011 to 2014. There are three main reasons I decided to return: the timing of the market, Castlight’s data-driven technology, and the team. Castlight has always had this magical culture, and I think Maeve O’Meara (Castlight’s CEO) has done an exceptional job building a world-class executive team and a fantastic group of customers that believe in what our team is doing and our vision of how we’re going to make healthcare and health benefits easier to use.

My role at Castlight is to help educate the market on the value that Castlight’s platform can unlock. I truly believe the version of Castlight we have right now—the intersection of data, navigation, and the human touch—is exactly what the market needs. Organizations everywhere are trying to simplify healthcare for their employees or members, and Castlight has done a really great job of harnessing the goodness of all the exceptional point solutions out there, as well as the various programs health plans offer, while still making it easy for individuals to navigate their personal health journey.

When leveraging the Castlight digital platform, a simplified and unified experience that positively impacts healthcare outcomes, and pairing it with the high-touch concierge service that our Care Guides offer, everyone wins—employers, health plans, members, and employees. I’m so excited to help tell that story.

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The pandemic has driven demand for platforms like Castlight Health, given today’s dynamics though – what are some of the biggest pandemic driven sales and salestech learnings you’d like to highlight?

The pandemic has been really difficult for everybody. I feel very proud of the work Castlight has done in an effort to help the country during a time of crisis. With the COVID-19 Test Site Finder, Vaccine Navigation, and VaccineFinder (which we partnered on with the CDC and Boston Children’s Hospital), we equipped our health plans and employer customers—in addition to the public—with trusted sources of data that allowed their members and employees to know exactly where they could get tested for COVID-19 or receive the COVID-19 vaccine.

With respect to sales, one of the things I’m continuing to learn is how thoughtful you have to be. I’ve never had a higher level of empathy for our health plan partners and our employer partners (and the consultants who support them)—they are in this crisis mode, from “How do I keep people safe?” to  “How can I get them to return to work?” You need to try your hardest to understand what they’re trying to accomplish. You may not fit in at this point in time, and you have to be very comfortable with that versus continuously pushing forward.

In addition, in a world in which many of us are working from home, we need to be really mindful about how and when we reach out to people and the expectations we have for them. People may seem more accessible, but they still have boundaries that should be respected. As a vendor partner, be really thoughtful when you’re trying to get time on somebody’s schedule.

Tell us about some of your upcoming (core) sales plans for Castlight Health?

The market is asking for health navigation to be a digital platform with a human touch. Castlight’s technology, personalization capabilities, and high-touch offering are best-in-class, but we can enhance our solutions even further by empowering our partners.

We’ve found that many of our competitors have turned health plans into the bad guys when they’re really not. Health plans are doing some really great things. They’re pushing advances in technology, and their disease management programs are getting better and better. And that’s a big part of our sales strategy—embracing health plans as valuable partners rather than treating them like the enemy. Our approach to digital health point solutions is the same. Castlight enables health plans and point solutions to accentuate their programs to their members, especially the members that need them most.

Our health navigation platform allows customers to pick the solutions that are best for their population. And no matter what they choose, Castlight’s platform will ensure members get the right care at the right time. In essence, customers can “pick their own adventure” and we can provide support with minimal disruption and high yield.

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As more and more businesses today are realizing the need to focus on employee health, how do you feel tech companies should cope up better globally to meet this?

I think digital health companies have struggled to work together over the past decade. They’re moving fast, they’ve got a message, and they’re very interested in telling their story. It will be more beneficial for large employers and health plans—and thus their employees and members—if companies in the digital health ecosystem can work more closely together, through deeper integrations instead of a fragmented infrastructure.

How should today’s sales and marketing leaders look at employee care and their own team growth and development, especially given the past year and a half?

Empathetic leadership is more important than ever. Make every effort to understand where each of your employees is during these unprecedented times; take the time and energy to listen to them. Also, manage your team, but coach the individual. For your team, there are set meetings, agendas, criteria, business processes, and so forth that need to be set. But when it comes to your one-on-ones, apply a very empathetic ear so you can recognize where each individual is coming from, then coach them with a tailored plan that will work for them. Everybody is different and needs different things, especially during times like these.

What do you think today’s sales and marketing leaders need to do differently to help them stand out from the crowd? 

Empathetic listening, collaboration, and knowing when you have a great opportunity versus when you don’t. Being able to disqualify yourself should be celebrated, not looked at as a loss. The sales cycle will happen a lot more naturally when you know where you fit best rather than when you try to force something to work.

Buyers are smart, and I think sellers need to listen better so they can really personalize the message. Learn as much about your buyer as you can. What’s most important to them right now? How full is their work plate? What critical view are they focusing on? Then see if it would be a good fit. By stepping softly and listening, you can potentially save time and energy for everyone. But when it is a good fit, it will be very clear—and you will win.

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Castlight is on a mission to make it as easy as humanly possible for people to navigate the healthcare system and live happier, healthier, more productive lives. As a leader in healthcare navigation, we provide a world-class digital platform with a team of clinical and benefits experts to help members easily connect and engage with the right programs and care, at the right time. Castlight partners with Fortune 500 companies and health plans to transform employee and member benefits into one comprehensive health and wellbeing experience to deliver better health outcomes and maximize returns on healthcare investments.

Frank Jennings brings more than 25 years of experience in business development and management of sales professionals in a variety of technology services centered around employee benefits. Most recently, Jennings served as chief commercial officer at Covera Health. Previously, Jennings led sales strategy as strategic advisor and senior vice president of Sales for Doctor on Demand, with additional sales leadership and new business development roles at Castlight Health, SuccessFactors, and ADP. His passion is anchored around helping technology companies that are committed to delivering better healthcare outcomes, devise their go-to-market strategy, and win market share.

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