Any HR leader will tell you that employee benefits planning today means balancing budget pressure, executive expectations, and a workforce shaped by emerging benefit trends and evolving support needs. The real challenge is determining where to invest, how to align with business priorities, and making sure your plan delivers measurable impact for your employees.
We turned to members of Cariloop’s HR Team, Chelsey Hershey, Vice President of People, and Concetta Pugliese, Manager of People Operations, for a candid look at how they approach employee benefits planning.
Start with Workforce Data & Employee Needs
Q: What do you consider first when approaching employee benefits planning?
Chelsey: We start by looking at what the data is actually telling us. Utilization trends and claims insights help us understand what employees are using and where gaps may exist, so we get a clearer view of where we are, and aren’t, delivering value to our team. Stepping back to look at that full picture helps us design benefits that truly meet employees’ needs while also supporting retention, workforce stability, and the company’s ability to execute on its business goals.
Then, we layer in engagement surveys and ongoing feedback from employees to better understand emerging needs that may not show up in the hard data. That combination of quantitative insights and lived employee experience has been powerful for us, and it’s where organizations can uncover the clearest signals about where to focus their benefits investments.
Q: What is the right cadence and approach for tracking employee feedback in benefits planning?
Concetta: We use post-enrollment surveys to get a pulse check on what resonated with employees and where we need to provide more clarity. The real insight that shapes our strategy comes from the conversations and feedback we receive throughout the year. We pay attention to recurring themes in employees’ questions and comments, since those patterns often point to gaps in awareness or access. I try to maintain an open door for benefit feedback, which allows us to make thoughtful, proactive adjustments to support resources and documentation.
Q: What factors should be shaping an employee benefits strategy that organizations may be overlooking?
Chelsey: Two factors we’ve found especially valuable are leave patterns and workforce demographics. We don’t just look at how many employees are taking leave, but why they’re taking it and how long they’re out. Those patterns reveal whether benefits are supporting short-term life events or longer-term caregiving responsibilities, and where gaps may be putting added strain on employees or making it harder for them to stay and thrive here.
Demographics matter just as much. At Cariloop, 82% of our workforce identifies as caregivers, which directly influences how we think about flexibility and family support for our benefits strategy. Regularly assessing the makeup of our workforce keeps our benefits strategy grounded in who our employees are and what they need as we build a stable and sustainable team.
Align Your Plan with Business Priorities
Q: In a constrained budget environment, how can HR determine where benefits dollars will have the greatest impact?
Concetta: Once we’ve identified the patterns in our data and feedback, the real work comes with deciding what to act on. With a limited budget, we choose to prioritize benefits tied to consistent, high-impact needs. For example, we recognize that the majority of our workforce are caregivers. As a result, we give every employee subsidized Backup Care and unlimited access to Cariloop’s coaching and platform to help them navigate their caregiving responsibilities so they can stay engaged and productive at work. This is one example of how we are directing dollars toward solutions that our team needs.
Q: How should HR leaders communicate the value of their employee benefits strategy to executive teams?
Chelsey: After priorities are defined, I shift my focus to making sure executive leaders understand the direction of our benefits strategy and prioritized investments. In those conversations, I advocate for our programs by painting a clear picture of what employees are using, where gaps have emerged from employee feedback, and how those insights informed the benefits we’re proposing. Framing the conversation this way helps our leaders connect these decisions to the outcomes they care about: retention, engagement, productivity, and overall workforce stability.
Drive Adoption Through Strategic Communication
Q: What does effective communication look like?
Concetta: Our ultimate goal is to make sure employees clearly understand what’s available, how to enroll, and where to go with questions. We build a communication plan that connects with employees through email, digital and in-office flyers, videos, Slack messages, manager trainings, and webinars. This multi-channel mix is important because employees absorb information differently. Having a thoughtful plan ensures they don’t just know what’s available, but understand its relevance to their lives and feel confident putting it to use.
Q: What role should leadership play in the rollout of a new employee benefits plan?
Chelsey: Leadership involvement can make or break a rollout. We spend time training leaders on our new benefits before anyone else. Since managers are the first stop for employee questions, giving them context early on what’s changing and why helps them communicate the benefits confidently to their team and prevents confusion once we launch.
Measure, Educate, and Optimize Year-Round
Q: What does continuous education and optimization look like in practice for a modern employee benefits plan?
Chelsey: For us, this is really about consistency. Benefits shouldn’t be something employees only hear about during open enrollment. Throughout the year, we look for natural moments to reintroduce resources, whether that’s around parental leave, back-to-school season, or when employees may be navigating new caregiving responsibilities. We also check in with managers and employees regularly on how benefits are being communicated and whether messaging still reflects what our team is navigating in real time. Staying attentive throughout the year allows us to continuously refine our approach so our benefits stay aligned with evolving workforce needs and remain relevant, visible, and easy to access.
Stay in the Loop
To close our conversation, we asked Chelsey and Concetta where they go for information and inspiration. Here are three resources they recommend:
Have questions or want to connect with this team? Find Chelsey and Concetta on LinkedIn.