Jennifer Chaloemtiarana, Castlight’s General Counsel, Wins a Corporate Counsel of the Year Award

At Castlight, we are on a mission to make it as easy as humanly possible to navigate healthcare and live happier, healthier, more productive lives. Each of our team members plays an important role in making this mission come to life, whether that is designing our product, working with customers, or ensuring compliance.

That is why we are very proud to see an important member of our team receive recognition for the great work she does each and every day. Jennifer Chaloemtiarana, who serves as our general counsel, chief compliance officer, and chief privacy officer, won the Corporate Counsel of the Year Award in the Pro Bono category from Silicon Valley Business Journal and the San Francisco Business Times.

Jennifer shared with us how she got involved in law, her role at Castlight, what she has learned throughout her career, and how the legal field has changed. Read below for the details!

How did you get started in law?

I took a slight detour out of law school.  I knew I was going to be a transactional lawyer, so a judicial clerkship did not appeal to me. However, in my third year of law school, my husband started a new job, so I agreed to stay in Michigan for an additional year, before heading to a firm in California.  I found a clerkship on the Sixth Circuit (with a judge that preferred to hire off-cycle) so I spent a year in a courthouse researching and writing.  It was a fantastic experience which sharpened my legal reasoning and analytical skills.

What is your main responsibility at Castlight?

I am the General Counsel, Chief Compliance Officer and Chief Privacy Officer, which is a significant role at a company that holds personal health information data.  This role includes the Legal, Security and IT functions.  Ultimately, though, I see my role as a “connector of people,” finding ways to pull disparate strands of information together to achieve efficient, smart solutions and drive well-informed decision making.

What made you become a lawyer?

I spent several years after college trying to figure out “What do I want to be when I grow up?”  The answer was right in front of me: my dad, Ben West, is a semi-retired real estate lawyer.  When I was a kid, his eyes would light up when he would talk about a deal he had put together, where both sides got something of value. He also has given his time generously to pro bono efforts.  I wanted a career that made my own eyes light up, and that would give me unique skills to invest in the community.

What is a fun fact about you?  

I like to try new unusual things that are outside of my comfort zone; one of my mottos is “Be comfortable with being uncomfortable.” A few recent examples are: I joined a soccer team as an adult, without ever having played as a kid; I started taking ballet lessons and danced in a local performance of the Nutcracker; I joined a hand bell choir even though I cannot read music (I have gotten very good at reading the G and A notes, since those are the only two that I play!).

What’s a memorable transaction where you had a successful outcome?

Two moments come to mind: The acquisition of Jiff, Inc. by Castlight Health has allowed us to expand our product offering into the most comprehensive health benefits platform on the market.  We can really improve people’s lives and access to care and wellness through the expanded platform.  Also, my role as the Chair of the Board of Directors of OneJustice, an organization that removes barriers to justice for millions of Californians through a variety of methods, has been very meaningful, especially in this past year where justice for low income people and immigrants has been under attack daily.

What’s the biggest change the legal profession has seen in the past decade?

A big change in the profession is taking place right now: the legal profession is evolving to be a positive force for change.  One of the things that drew me to the work of OneJustice was hearing the CEO, Julia Wilson, say “Lawyers can be heroes.”  I have seen this in action again and again in this past year, from the work at the pop-up clinics at airports to the pro bono legal challenges being played out in courts right now to protect the civil rights of the underserved and underrepresented.  I am proud to be a part of this community.  

What’s the biggest professional challenge you’ve overcome and how did you do it?

I don’t have one specific challenge that comes to mind, but I have overcome a series of smaller challenging moments where I had to express my own voice, my own position, and my own value system without reservation.  I overcome these moments by just asking myself:  What is truly right in my own mind and heart?  Then I let the chips fall where they may.  I have never had a single regret when I have followed this decision-making system.

What’s the biggest legal issue or challenge you anticipate facing in the next year?

Navigating the ever-changing landscape of privacy regulations and how those intersect with business goals is top of mind.  Also, keeping my team happy and motivated in a high-pressure environment is a top priority.

What’s the best free legal advice you have for business owners?

Treat your employees with respect on the way in and on the way out.  You can never go wrong by doing so.

What is the best advice you’ve ever received?

“If you only do what you can, you will never be more than you are now.”  This is the underpinning of why I like to try random, new things, like joining a bell choir.  And believe it or not, I heard this quote in the fine film “Kung Fu Panda 3”.  Inspiration can come from surprising places!

Congratulations on this great honor, Jennifer. We are lucky to have a strong leader like you on Castlight’s senior leadership team. Your achievements, both professionally and personally, are an inspiration for us all.