Enrollment Essentials: Setting Your Team Up for Success

As Chief People Officer, one of my favorite times of the year is benefits enrollment season. Yes, you read that right—I genuinely love this time! While it might seem like a mountain of paperwork and decision-making for everyone involved, I see it as our annual opportunity to reinforce our commitment to our team's wellbeing and future security.

The truth is, benefits enrollment isn't just about checking boxes or meeting compliance requirements. It's about creating a comprehensive safety net that allows our people to thrive both at work and at home. When employees feel secure and supported, they bring their best selves to everything they do.

The Foundation: Core Benefits That Matter Most

Let's start with the essentials, the benefits that form the bedrock of any solid compensation package. These aren't just nice-to-haves; they're fundamental to attracting and retaining top talent while ensuring everyone on your team can focus on what they do best.

Medical coverage sits at the heart of this foundation. We've all learned how quickly health circumstances can change, and having robust medical coverage isn't just about peace of mind; it's about ensuring our people can access quality care when they need it most. When evaluating medical plans, I always think about our diverse workforce and try to offer options that work for different life stages and family situations.

Paid Time Off is equally critical, though it's often undervalued. We're not just offering days away from work; we're actively supporting work-life balance and recognizing that rest and rejuvenation are essential for long-term performance. Whether someone needs time for a family vacation, personal appointments, or simply to recharge, PTO sends a clear message that we value our employees as whole people, not just workers.

Some organizations separate sick leave from general PTO, and there's real wisdom in this approach. When people feel pressure to use vacation days for illness, they're more likely to come to work sick, which isn't good for anyone. Dedicated sick leave removes that internal conflict and supports both individual health and workplace wellness.

The 401(k) with company match is where we get to be partners in our employees' futures. Every dollar we contribute to someone's retirement is an investment in their long-term financial security. It's also one of the most appreciated benefits, especially as people become more aware of the importance of retirement planning. Even a modest match can make a significant difference over time.

Employee Assistance Programs (EAPs) might be the most underutilized benefit we offer, but they're incredibly valuable. Life happens—family stress, financial concerns, mental health challenges, legal questions. Having professional support available 24/7 at no cost provides a crucial resource that many people need but might not otherwise access.

Finally, Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA) offer practical ways for employees to manage healthcare costs with pre-tax dollars. These accounts help stretch healthcare budgets further while providing tax advantages—it's a win-win that supports both immediate needs and long-term financial wellness.

Going Beyond the Basics: Voluntary Benefits That Add Real Value

While core benefits provide the foundation, voluntary benefits allow employees to customize their coverage based on their unique circumstances and priorities. These options demonstrate that we understand our workforce isn't one-size-fits-all.

Vision and dental coverage might seem routine, but they address real, ongoing expenses that can add up quickly. Regular dental cleanings and eye exams are preventive care that keeps people healthy and productive. Plus, when someone doesn't have to worry about the cost of glasses or dental work, they're more likely to stay on top of these important aspects of their health.

Floating holidays have become increasingly popular, and for good reason. Our teams come from diverse backgrounds with different cultural and religious observances. Floating holidays provide flexibility while acknowledging that not everyone celebrates the same holidays. This small gesture can mean a lot to employees who feel seen and respected for who they are.

DP Cares. This is an additional 2 weeks of paid leave per year for an employee who is struggling to care for a loved one who is experiencing a medical situation. We initially created this leave program to bridge the gap between the birth and when STD kicks in for new moms, but quickly recognized that this was a need across the organization for any employee who might need time away to care for an aging parent, a spouse recovering from surgery, a sick child, etc. We did not want our employees to have to use up all of their PTO for these life issues.

Short-term and long-term disability insurance addresses what many consider unthinkable scenarios, but the reality is that accidents and illnesses can happen to anyone. These protections ensure that if someone can't work due to disability, they'll still have income to support themselves and their families. It's the kind of coverage people hope they'll never need but are incredibly grateful to have if circumstances change.

The Extras That Make a Difference

Some benefits might not be standard across all organizations, but they can set you apart as an employer that truly invests in people's growth and well-being.

Tuition reimbursement signals that we're committed to our employees' professional development and career advancement. Whether someone wants to complete a degree, earn a certification, or develop new skills, educational support shows we're invested in their future, both with us and beyond.

Maternity and paternity leave (beyond what's legally required) acknowledges that welcoming a new family member is a significant life event that deserves adequate time and support. Generous family leave policies help ensure that new parents can bond with their children without worrying about job security or finances during this critical time.

Savings accounts or additional retirement options like "sunny day" funds give employees more ways to build financial security. These might include emergency savings programs, additional retirement vehicles, or other financial wellness tools that help people prepare for both expected and unexpected expenses.

Making Enrollment Season Successful

The best benefits package in the world doesn't help anyone if employees don't understand or enroll in what they need. This is where clear communication and support during enrollment become crucial.

Start early with education sessions that explain not just what's available, but why it matters. Use real examples and scenarios that help people understand how different benefits might apply to their lives. Consider offering one-on-one consultations for employees who want personalized guidance.

Remember that benefits decisions can feel overwhelming, especially for younger employees who might be navigating these choices for the first time. Create resources that break down complex topics into digestible information, and don't assume everyone understands insurance terminology or retirement planning basics.

The Bigger Picture

At the end of the day, a comprehensive benefits package is about more than individual policies and programs. It's about creating an environment where people feel valued, supported, and secure enough to do their best work. When employees know that their health, financial security, and personal wellbeing matter to their employer, it builds the kind of trust and engagement that drives organizational success.

Enrollment season is our annual opportunity to reinforce these values and help our team members make choices that will serve them well throughout the year and beyond. By offering thoughtful, comprehensive benefits and supporting people through the enrollment process, we're not just checking a box—we're investing in the foundation of a thriving workplace culture.

The time and resources we put into getting benefits right pay dividends in employee satisfaction, retention, and performance. More importantly, they reflect our values and commitment to treating our people as whole human beings deserving of support, security, and care.

Don't forget to send out an annual benefits satisfaction survey to gather usage data and feedback from your team. This valuable insight helps you understand which benefits are truly making a difference and which might be underutilized. If you discover that employees aren't engaging with certain offerings, you can reallocate those resources toward benefits that better meet their needs and preferences—ensuring your benefits investment delivers maximum value for both your people and your organization.

Want to learn more about Open Enrollment Essentials?

Join our upcoming webinar, Open Enrollment Essentials: Setting Your Team Up for Success, on Tuesday, July 22nd. REGISTER TODAY »