A Day in the Life of a HealthJoy Regional Sales Executive

Welcome to HealthJoy’s new “Day in the Life” series. We want to pull the curtain back on life at HealthJoy and give you a behind-the-scenes look at the many teams that help inject some joy into your healthcare and benefits experience.

For our first installment, we talked to Regional Sales Executives (RSE) Amber Cassar and Brett Aprati to learn all about the sales team and what a day in their role looks like. 

RSEs are spread out all over the country and each has a sales territory they manage. And if you’re a HealthJoy member, chances are an RSE got the ball rolling at your company with a phone call, email, or conversation at a conference. 

Enough from me, let’s hear directly from Brett and Amber on their day-to-day at HealthJoy!

What makes HealthJoy's sales organization different from other places you've worked?

Brett: I’d say it boils down to three things.

1. Our commitment to simplifying healthcare for our clients and their employees. 
2. Our transparency about our vision, goals, and company challenges, as well as our accomplishments. 
3. No day or week is the same. Every day brings a new challenge, new opportunity, or new relationship forward.

Amber: The HealthJoy sales team is truly supportive of one another and truly enjoys being together, whether that's onsite or on Zoom. Although we have individual goals, we're all invested in our mutual success.

What's your favorite part about working at HealthJoy? Any specific favorite memories of working here?

Brett: The people and the mission! Our mission is to simplify the healthcare and benefits experience for every member. It drew me to work at HealthJoy and keeps me motivated because like most people, I’ve seen how complicated the US healthcare system can be.

And the people are genuinely great teammates! Everyone is friendly, helpful, and moving towards similar goals.

Amber: I’ve really enjoyed the company Slack channel #healthjog, where all the runners at HealthJoy talk about their training for upcoming races. It’s been a great way to learn more about my colleagues outside the sales department and support each other as we reach some personal goals. 

It actually got me back into running after a five-year hiatus. Most members of the channel ran the Chicago Marathon in October, and I'll be completing my half marathon in Charlotte this November!

What does a typical day look like for HealthJoy Regional Sales Executives?

Brett: My morning usually kicks off in a similar way: 

• Checking my email
• Preparing for the day's meetings and demos
• Addressing any final preparation items

After that, I’ll provide any deliverables from the previous day's demos and meetings. As you can see, mornings are a critical time to keep everything organized for the day ahead.

My afternoons vary a lot by day and week, which keeps the role exciting for me. But usually, I’m involved in meetings and demos for both brokers and prospects. 

I also use afternoons to address any follow-up items from the day or previous discussions I’ve had. Other than that, it’s a mixed bag of ongoing outreach to brokers, prospects, and partners surrounding new opportunities, pipeline deals, and coordinating meetings and events.

Amber: Each morning I like to run a quick scan to get me up to speed for the day. This usually includes looking into relevant website hits, inbound leads, and LinkedIn activity. I also like to use mornings to explore some creative opportunities to reach out to partners and companies that are considering HealthJoy.

By the time the afternoon hits, I’m usually diving into product demos and strategy conversations. Our business is very seasonal, so it can really switch up what’s on my plate. Sometimes I connect with benefits consultants to show them a live HealthJoy demo. While other times I'm helping clients picture what it’d be like to have HealthJoy at the fingertips of their workforce. 

What does a typical day after work look like for you?

Brett: I’m usually playing the role of chauffeur and running around with my kids to practices or games for whatever sport is in season. If they don’t have any sports that day, I like to go out for a walk with my wife and kids or to play sports. We enjoy a wide range of sports and you can find us playing tennis, soccer, or lacrosse. Outside of sports, we enjoy the outdoors and you can often find us fishing or biking.

Amber: After work, I usually beg my two little boys to "take me outside to play." Usually, that means swinging on the tree swing or fighting imaginary ninjas in the backyard. Thankfully, we still have an undefeated record in those imaginary battles.

What can HealthJoy do for you?

Thanks again to Brett and Amber for giving us an all-access look into their day-to-day as Regional Sales Executives. If this role sounds like a fit for you, be sure to check out our careers page. 

We’re currently hiring for a number of roles, including Regional Sales Executives. And as always, we’re a remote-first company focused on building a diverse team that’s passionate about simplifying the process of being healthy and well.