Top Challenges Health Insurance Benefits Professionals Are Facing Today

As the year winds down and open enrollment ramps up, health insurance challenges seem to multiply. But here’s a look behind the curtain at the top challenges benefits professionals face year-round—and why they deserve more credit than they often get.
Why it’s a big deal:
Competitive benefits play a major role in attracting and retaining top talent. But finding that sweet spot—where the benefits are robust, yet affordable—is like juggling flaming swords. Managing the challenges requires deep knowledge of the health insurance market, an understanding of employee priorities, and some serious negotiation skills with insurance carriers.
What’s at stake? Offer too little, and employees will head for greener pastures but spend too much, and the company’s bottom line takes a hit.
The result? Benefits professionals spend hours analyzing coverage details, comparing plans, and ensuring they’re worth the cost. It’s not just about numbers; it’s about finding value.

- Younger employees might prioritize student loan assistance or wellness programs.
- Mid-career professionals might focus on comprehensive healthcare or family leave.
- Older employees might want robust retirement benefits and long-term care options.
The challenge?
- Benefits professionals need to craft packages that check as many boxes as possible without overcomplicating the offerings. It’s about balancing flexibility with feasibility, which can feel like walking a tightrope blindfolded.
The Admin Avalanche
Beneath the surface of those glossy open enrollment emails and neatly organized benefits portals lies a mountain of administrative tasks that benefits professionals climb daily.
What they’re juggling:
- Processing enrollments and terminations for new hires and departing employees.
- Handling errors like lost coverage or incorrect deductions.
- Navigating endless questions from employees, carriers, and everyone in between.
Why it’s challenging:
- Benefits professionals are essentially the “fix-it” team for every issue under the sun. An employee’s coverage unexpectedly disappears? They’re on it. The insurance carrier made an error? They’ll sort it out. Someone doesn’t understand what an HSA is? Time for an impromptu benefits 101 session.
The kicker:
- This all happens while they’re also planning open enrollment, evaluating new vendors, and keeping up with compliance changes. To say they’re multitasking is an understatement.
Here’s a question: How many employees can confidently explain their benefits package? If your guess is “not many,” you’re not alone.
The disconnect – Employees often view benefits as something to deal with once a year during open enrollment, and then promptly forget about until they need them. Meanwhile, benefits professionals are working tirelessly to create informative materials, host webinars, and answer questions.
The frustration – Employees don’t read the communications, or they don’t attend the info sessions. Unfortunately, when they do engage, it’s often at the last minute, or worse, after a deadline has passed.
Why it matters – When employees don’t understand their benefits, they can’t make informed decisions. This can lead to dissatisfaction, avoidable expenses, and unnecessary stress, both for the employees and the benefits team.
The uphill battle – Getting employees to engage requires creativity, persistence, and sometimes a touch of humor. It’s about making benefits feel approachable and relevant while cutting through the noise of overflowing inboxes and workplace distractions.
Why Benefits Professionals Deserve A Round of Applause
So, the next time you find yourself navigating your benefits portal or asking a question about coverage, take a moment to appreciate the hard work that goes into making it all possible. Behind every plan, policy, and portal is a team of benefits professionals who genuinely care about making your life better, even if you don’t notice them.
As we head into the busiest season for most benefits teams, let’s give them the recognition they deserve. And if you’re a benefits professional reading this? Take a deep breath. You’re doing amazing work, and it doesn’t go unnoticed.
Here’s to you: the champions of healthcare plans, the wizards of wellness programs, and the masters of multitasking. The workplace wouldn’t be the same without you!

Legal Disclaimer:
The information in this website is provided for general informational purposes only, and may not reflect the current law in your jurisdiction. No information contained in this post should be construed as legal advice from CobraHelp. or the individual author, nor is it intended to be a substitute for legal counsel on any subject matter. No reader of this post should act or refrain from acting on the basis of any information included in, or accessible through, this Post without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer licensed in the recipient’s state, country or other appropriate licensing jurisdiction.
The Employee Benefits That Make A Difference: What Employers Need to Know

Moreover, employees with health insurance are more likely to seek out preventative care. When people are covered, they are more inclined to get regular check-ups, screenings, and follow necessary treatments. This proactive approach not only keeps individuals healthier, but it also reduces absenteeism and increases productivity in the workplace. In essence, investing in health benefits is an investment in your employees’ long-term well-being and your company’s overall success.
Takeaways:
- Health benefits give employees the security they need to deal with life’s uncertainties.
- Coverage encourages preventative care, leading to healthier, more productive employees.
- Access to healthcare for employees and their families promotes overall well-being.
Takeaways:
- Dental and Vision benefits reduce the financial burden on employees, allowing them to focus on their work and personal lives.
- Healthy employees are happier and more productive, and dental/vision benefits contribute to that.
Employees want to know that they will have time to recharge, take care of personal matters, and enjoy life outside of work. Providing a reasonable amount of paid time off is not just a luxury—it’s an investment in the well-being of your workforce. Time away from work leads to reduced burnout, increased job satisfaction, and better overall performance when employees return.
Paid time off typically includes vacation days, sick leave, personal leave, and holidays. Additionally, many employees now seek parental leave or other family-related leave benefits to support them during significant life events. Employees who feel supported by their employer during life’s milestones—whether that’s the birth of a child or caring for a sick family member—are more likely to be loyal, engaged, and committed to their role.
Takeaways:
- Paid time off is crucial for a healthy work-life balance, reducing stress and burnout.
- Employees with time to recharge are more productive and engaged.

Employees want to feel confident that they are building a secure financial future and knowing that their employer is helping them save for retirement provides a sense of stability and security.
Retirement plans also act as a powerful retention tool. Employees who have access to decent employer-contributed retirement savings programs are more likely to stay with a company long-term. It shows that the employer is committed to helping them achieve financial independence and peace of mind in their post-working years. Employers can make these plans even more attractive by offering matching contributions or additional financial planning services.
Takeaways:
- Employer-sponsored retirement plans help employees plan for a secure future.
- Retirement benefits demonstrate a long-term commitment to employee well-being.
- Offering retirement benefits can help retain employees and reduce turnover.
- Offer Comprehensive Health Coverage: Ensure that your health benefits plan is comprehensive and affordable. Offering a variety of plans or flexible options will appeal to employees with different needs and family situations.
- Communicate Benefits Clearly: Make sure your employees understand the benefits available to them. Regularly communicate updates, changes, and the value of each benefit. This will help employees appreciate what they’re receiving and how it can positively impact their lives.
- Encourage Regular Health Screenings: Promote wellness by encouraging employees to take full advantage of their health, dental, and vision benefits. This can foster a culture of health within your workplace.
- Foster a Positive Work Environment: PTO is only valuable if employees feel they can take time off without guilt or negative repercussions. Promote a culture that values time away from work and encourages a healthy work-life balance.
- Invest in Long-Term Financial Planning: Retirement plans are key to long-term employee satisfaction. Be sure to offer a plan that employees can rely on and consider providing financial literacy workshops or consulting to help them plan for their futures.

Ultimately, investing in your employees’ well-being is an investment in the future success of your company. By aligning your benefits offerings with the needs and priorities of your employees you are helping your team thrive. Thus, ensuring your company remains a great place to work for years to come!
The information in this website is provided for general informational purposes only, and may not reflect the current law in your jurisdiction. No information contained in this post should be construed as legal advice from CobraHelp. or the individual author, nor is it intended to be a substitute for legal counsel on any subject matter. No reader of this post should act or refrain from acting on the basis of any information included in, or accessible through, this Post without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer licensed in the recipient’s state, country or other appropriate licensing jurisdiction.
Supporting Your Employees Through COBRA: A Guide for Employers

Acknowledge the Confusion
When employees lose their jobs, they often face a whirlwind of emotions and uncertainties. The transition to COBRA can add to this stress. It’s essential to acknowledge that many employees may find this process confusing and overwhelming. By recognizing this, Employers can approach the situation with empathy and understanding, reassuring them that assistance is available.
Reporting a COBRA Qualifying Event
Any successful transition starts at the beginning. When it comes to COBRA coverage, timely reporting of a qualifying event is crucial. To ensure a smooth transition to COBRA benefits, it’s best to report the event—such as their last date worked—immediately or as close to that date as possible. This helps avoid any lapses in coverage and allows CobraHelp to issue the necessary election notice promptly. The sooner you act, the greater the chances of minimal interruption in active benefits.
Connect Them with CobraHelp
One of the most effective ways to support employees is to inform them about CobraHelp. Our dedicated service specializes in COBRA administration and has a team of COBRA Participant Specialists ready to assist employees (and employers) with any questions they might have. It isn’t a call center where representatives are reading off of a script. Instead, members with CobraHelp receive the support and personalized service that they need. Encourage employees to reach out to CobraHelp directly for guidance on their coverage options, paperwork, and deadlines. This connection can help alleviate some of their anxiety and provide them with the expert support they need.

About the Author:
Ryan Bowman is a certified C.O.B.R.A. Expert who has served hundreds of CobraHelp clients as both a Account Manager and a Data Integrations Lead. Ryan is known for his savvy when it comes to compliance administration and his keen attention to every detail.
Legal Disclaimer:
The information in this website is provided for general informational purposes only, and may not reflect the current law in your jurisdiction. No information contained in this post should be construed as legal advice from CobraHelp. or the individual author, nor is it intended to be a substitute for legal counsel on any subject matter. No reader of this post should act or refrain from acting on the basis of any information included in, or accessible through, this Post without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer licensed in the recipient’s state, country or other appropriate licensing jurisdiction.