Common Payroll and Benefits Challenges
June 16, 2025 at 10:00 PM
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How Employee Engagement Specialists Can Help

Managing payroll, benefits, and employee health plans can be overwhelming. Most HR teams and business owners are balancing cost control, compliance, and employee satisfaction all at once. And when you add employee engagement to the mix? Things get even more complicated.

At H2H Enrollments, we get it. We're not just a benefits broker or a payroll provider—we're an extension of your team. From hire to retire, we handle the details so you can focus on your people and your business. In this post, we’ll walk through the most common challenges companies face with payroll, benefits, and proactive health management—and how working with an employee engagement specialist can solve them.

1. Payroll Problems That Drain Time and Money

Let’s start with payroll. Whether you’re a small business or managing hundreds of employees, even minor errors can turn into major issues—late payments, tax penalties, or compliance risks.

Common payroll pain points:

  • Manual data entry leading to errors

  • Misclassified workers (W-2 vs 1099)

  • Inconsistent pay cycles

  • Missed tax filings or incorrect calculations

  • Lack of integration between payroll and HR systems

These issues not only frustrate employees, but also increase workload for HR. That’s where we come in. H2H Enrollments offers a fully integrated payroll solution that connects with benefits and compliance tools. No more juggling systems or re-keying data.

When you bring in an employee engagement specialist, you also make sure your payroll communications are clear, your employees feel confident about their pay, and questions get answered quickly.

2. Benefits Confusion That Hurts Retention

Too many benefits options can be just as stressful as too few. Employees often don’t know what they’re signing up for—or worse, skip enrollment altogether because it feels overwhelming.

Top challenges we see:

  • Employees don’t understand their benefit choices

  • Companies struggle to offer competitive packages

  • Outdated platforms make enrollment confusing

  • Lack of customization for different employee groups

Benefits shouldn’t be a guessing game. That’s why we offer benefits bundles that are designed to work together—health, dental, vision, life, disability, and more. We also help employers design cost-effective packages that balance employee needs with business goals.

Here’s the big difference with H2H: our employee engagement specialists lead your open enrollment. We meet with employees, answer questions, and make sure everyone knows how their choices affect their health and wallet. It’s personal. It’s clear. It’s efficient.

3. Lack of a Proactive Health Management Plan

Employee wellness is no longer a “nice-to-have.” If your business doesn’t have a proactive health management plan, you’re likely paying more in claims, seeing more absenteeism, and dealing with burnout.

Reactive healthcare—only helping employees after they’re sick—drives up costs. Instead, proactive plans focus on early intervention, education, and preventative care.

What proactive health plans include:

  • Regular health screenings and biometric testing

  • Wellness coaching and mental health support

  • Preventive care incentives

  • Chronic disease management

  • Nutrition, exercise, and stress-reduction tools

It’s not just about physical health. Mental health matters too—and younger employees expect support in this area. A strong health management plan helps reduce turnover, boost productivity, and lower claims costs.

Our team helps employers choose and customize plans that match their workforce needs. Then, our employee engagement specialists work directly with employees so they actually use what’s offered.

4. Juggling Too Many Vendors and Systems

One of the biggest frustrations we hear? Employers working with multiple vendors who don’t talk to each other. One handles payroll. Another does compliance. A third runs open enrollment. Nothing is integrated, so HR ends up doing twice the work.

That’s why H2H Enrollments was built as a one-stop shop. You don’t have to cobble together different providers or chase down answers. We offer:

  • Integrated payroll and benefits

  • Compliance support

  • Self-service logins for employees

  • Custom packages—use only what you need

  • Full hire-to-retire services

And yes, our employee engagement specialists are with you the entire time. Whether it’s onboarding a new hire or rolling out a new health plan, we make sure your employees know what’s happening—and feel supported through every step.

5. Communication Gaps That Hurt Engagement

Even the best payroll or benefits system falls flat if employees don’t know how to use it. Clear communication is key. But most HR teams don’t have time to field every question or hold individual meetings with staff.

That’s why engagement matters. When employees understand their pay, benefits, and wellness tools, they’re more likely to use them—and stick around longer.

Our employee engagement specialists step in to bridge this gap. They explain complex topics in simple language, guide employees during key transitions, and handle the heavy lifting during open enrollment. It’s not about giving employees more choices—it’s about giving them the right tools and support to make smart decisions.

Better Support Starts with the Right Partner - H2H Enrollments

Payroll and benefits are the backbone of a great employee experience. But without the right support, they can quickly become a source of stress and turnover. That’s why having a trusted partner like H2H Enrollments matters.

We’re large enough to offer fully customized solutions—and small enough to be agile when you need us. Whether you’re starting from scratch or just need help in one area, we’ll work with you to build a solution that fits your people and your budget.

Want to see what this looks like for your team?

Contact us talk with one of our employee engagement specialists today. Let’s simplify payroll, benefits, and wellness—together.