How Two Real-Life Benefits Leaders are Getting Creative This Open Enrollment

How is open enrollment like an art project? 

Well, as you might have experienced in the past few years, connecting the right employees with the right benefits requires a lot more creativity than it used to. With five different generations in the workforce, more benefits offerings than ever, and employees spread out across the country (or world), it takes a crafty benefits pro to develop open enrollment messaging that resonates and drives action.

But if you’re lacking inspiration as 2024 open enrollment approaches, don’t worry. We turned to the artists themselves—Katie Richards of Corewell Health, and Matthew Pettit of Wawa—to find out how they’re coloring outside the lines to drive greater benefits engagement. 

Here are the unique, out-of-the-box tactics they shared during Camp Engage!

Meet the Speakers

Katie Richards

Senior Benefits Analyst,

Corewell Health


Matthew Pettit

Manager of Benefits,


Corewell Health: There’s no such thing as starting too early

The challenge: 

Last year, two large health systems in Michigan joined together to become Corewell Health. While the merger is a huge opportunity to expand business, leverage new resources and better serve customers, it also poses a unique challenge at open enrollment: as a large healthcare system, Corewell is an employer, an insurer, and a healthcare provider. That means plan designs and strategies get complicated quickly, and Corewell’s benefits team was faced with communicating to a new workforce that’s twice as big as it used to be.

Employees pre-merger
Employees post-merger
"It’s truly exciting, but very nerve wracking. There were lots of unknowns in terms of how our employees would react to these benefits changes."
Katie Richards
Senior Benefits Analyst, Corewell Health

The solution: 

The Corewell Health team realized that helping employees engage with complicated benefits designs required a multi-pronged approach. So they used several tactics to improve their benefits communications at open enrollment (and beyond). 

Make ALEX a part of the team

As a 24/7 resource that leverages behavioral science and predictive analytics to offer personalized benefits recommendations, ALEX was a crucial component of Corewell’s open enrollment communication strategy. 

When employees approach HR with a benefits question, they’re sent to ALEX first. And the benefits team found creative ways to ingrain ALEX into Corewell’s existing company culture, too. During a recycled art contest, HR folks created an ALEX blobby to remind employees about the benefits resources at their fingertips:

ALEX blobby made from recycled materials.
"We’ve all had that heart wrenching moment when an employee says, ‘I didn’t know about that benefit you offer.’ Communication and education is so important to make sure your resources are actually used and seen."
Katie Richards
Senior Benefits Analyst, Corewell Health

Communicate early and often

At Corewell, benefits communication starts in January—a full ten months before open enrollment begins. Katie finds that a year-round approach not only drives engagement and ensures employees are actually using the resources they signed up for, but it also helps her team understand which messages are resonating. 

By using email software to send bi-monthly communications, Katie and her team can track open rates and click-through rates to see which topics are most relevant to employees, and which communication strategies are most likely to drive action. 

What’s inside those emails? Listen to Katie explain: 

As the deadline to a November open enrollment approaches, Katie and her team pick up the pace. Starting in September, communications ramp up to bi-weekly, providing employees with bite-sized details on all of Corewell’s benefits offerings.

"Providing little pieces of information throughout the year that continue to show all the different benefits offerings is my favorite part of being a benefits professional. We get to deliver messages about programs that benefit our team members above and beyond base salaries."
Katie Richards
Senior Benefits Analyst, Corewell Health

And, as Katie shared, the real secret to crafting a benefits message that cuts through the noise is to ask yourself, “WWAD?”

"We often ask, ‘What would ALEX say? How would ALEX present this benefit? The answers are casual, fun, easy, exciting, over-the-top, and relatable. ALEX is a true benefits expert and a valued member of our team."
Katie Richards
Senior Benefits Analyst, Corewell Health

Wawa: Take a look at yourself and make that change

The challenge:

With 1,000 East Coast convenience and fuel stores and 12,500 benefits-eligible retail employees, Wawa’s benefits team operates much differently than those in other industries. Retail associates don’t have a company email address or phone number, so traditional open enrollment communication channels don’t apply. And with stores spread out across multiple states, HR team members aren’t close by to answer benefits questions or communicate to each individual associate. So they were left with a question: how do we get the right benefits information to the right people, at the right time?

The solution:

First, Wawa’s benefits team knew they needed to do some research to find out which open enrollment tactics were working, and where they needed to improve. From there, they identified a unique communication channel—their store managers—to relay important benefits information to retail associates. 

Run a benefits focus group

To drive greater benefits engagement, Wawa’s benefits team first took a step back: to reflect on their open enrollment strategies and identify trouble spots for employees. They invited representatives from every state Wawa serves to a benefits focus group, where they explored which resources were already popular, how employees prefer to learn about their benefits, and what feedback employees had on Wawa’s current benefits materials. 

"The ultimate takeaway was that there’s no consensus. There’s no magic, single communication path for everyone."
Matthew Pettit
Manager of Benefits, Wawa

As all of us in the HR world have come to realize, the focus group didn’t surface a single solution that would work for every employee. Instead, Wawa’s benefits team realized they’d need to create a blanket strategy that shared as much information in as many places as possible, all centered around one crucial communication channel. 

Make managers your megaphone

Because Wawa retail associates don’t have a company email address or interact with HR often, their store managers are their main point of contact. So Wawa’s benefits team brought all 1,000 managers together in June, well before open enrollment, to brief them on upcoming procedures and offer a deep dive into this year’s benefits packages. 

While there was no expectation that store managers would actually help guide their associates towards smarter benefits decisions, Matthew and his team armed them with the resources they needed to point associates in the right direction. 

"Creating a singular, centralized hub for all of our benefits offerings was one of the biggest takeaways from our focus group. It’s a tool for managers to give their associates, where they can go for more information—because we’re not expecting managers to actually tell their teams which plans to enroll in. ALEX and our benefits hub are a stand-in for HR."
Matthew Pettit
Manager of Benefits, Wawa

Blast away

While a targeted, personalized communication strategy is smart for many companies during open enrollment, Wawa’s unique company structure lends itself to a different approach, which Matthew calls the “Blast Away” method. 

"We use a ‘blast away’ approach to connect with hard-to-reach employees. We put benefits information everywhere we can: direct mail, our intranet, an internal social media platform, backroom signage, virtual presentations and video recordings, and more."
Matthew Pettit
Manager of Benefits, Wawa

With newly branded benefits materials that better reflected Wawa’s external look, feel, and tone, Matthew and his team used a guerilla marketing approach to spread the word far and wide. They digitized open enrollment resources to make the content more interactive, with embedded videos and the ability to navigate to different topics or visit provider websites. They created an open enrollment guide that highlights only the most important things employees need to know: 

  1. What’s new? 
  2. What are my action items? 
  3. What should I expect after I enroll? 

And of course, ALEX helped tie it all together, by offering personalized guidance when a store manager or HR rep wasn’t available to answer questions: 

of associates said they had a better understanding of medical benefits with ALEX
0 %
visits to ALEX during open enrollment

If Katie and Matthew taught us anything during their Camp Engage session, it’s this: one size does not fit all at open enrollment. It’s all about exploring which communication methods are the right fit for your employee population, industry, company structure, and more. So pull out those hypothetical paint brushes, get a little messy, and brainstorm how you can be a bit more creative in your communication strategy this year. You might just be surprised what you and your team can come up with, and how well your employees will respond! 

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