By Dave Shore, Borislow Insurance

Most employers feel reasonably comfortable – or at least loyal – to their current broker relationship. On the surface, everything seems fine. But when we start asking deeper questions, it often becomes clear that many organizations have simply grown accustomed to a renewal cycle that doesn’t truly serve them or their people.

The Commute No One Wants

If you’ve ever been stuck in rush hour, you know the feeling. At best it’s a miserable crawl forward. At worst, there’s a full-on car wreck that brings everything to a standstill. For many organizations in the small to mid-market, the annual benefits renewal process feels the same. Each year, your broker shows up late in the cycle with a spreadsheet that illustrates you’ll need to pay more and get less. You’re presented with a few flashy alternatives that don’t really fit your business reality. Then, with little time left on the clock, you’re forced into rushed decisions – without meaningful data and with barely enough time to communicate changes to your employees. It’s the benefits equivalent of gridlock: frustrating, inefficient, and leaving you to wonder why this is the only way forward.

Why It Feels This Way

Over time, employers have been conditioned to believe that this process is “just how it works.” The same congested highway. The same bottlenecks. The same powerless feeling. But the truth is, there is another way. At Borislow, we believe employers shouldn’t be victims of the renewal cycle. By starting earlier, leveraging predictive analytics, and understanding your organization’s risk profile, you can make thoughtful decisions that align strategy with value. Done right, you’re no longer stuck in traffic – you’re flying above it.

Signs It’s Time to Rethink the Relationship

If you only hear from your broker at renewal time

A once-a-year call to talk renewal isn’t a strategy. In today’s environment – with escalating costs and shifting regulations – you need an advisor who is in dialogue with you throughout the year. If your broker only appears annually with bad news, they’re managing transactions, not guiding your business.

If your broker isn’t bringing data to the table

Spreadsheets illustrating disappointing alternative options alone aren’t enough. Employers without traditional access to claims data deserve predictive analytics and a clear view of their risk profile. Without those insights, you’re essentially driving blind. If your broker isn’t equipping you with real data early in the process, they’re not setting you up for proactive, intentional decisions.

If strategy isn’t aligned with your company’s growth

Your benefits strategy should evolve alongside your business. A rapidly growing workforce requires a different approach than a stable, mature organization. If your options feel generic year after year, your broker likely hasn’t taken the time to align benefits strategy with your business strategy.

If renewal always feels rushed and chaotic

The renewal process will never be effortless, but it also shouldn’t feel like a multi-car pileup every year. If you’re constantly facing short timelines, limited options, and rushed communications, that’s a process failure. A better approach starts months earlier, educates you along the way, and only marries concepts to pricing after you’ve had time to reflect on what makes sense for your business and people.

Loyalty Where It Matters Most

Relationships matter, and most brokers genuinely care about their clients. But as a fiduciary, your loyalty doesn’t belong to a broker or a vendor. It belongs to your employees and their families – the people who rely on you to provide affordable, high-quality care.

If your current broker isn’t helping you get there, it may be time to rethink the relationship. You don’t have to accept gridlock forever. There is a better way forward.

By April McCabe, Senior Client Consultant at Borislow Insurance

When I talk to employers about Captivated Health, the first thing I tell them is simple: it allows you to own your health plan. That ownership creates opportunity to contain costs, design benefits that actually fit your employees, and build a long-term strategy aligned with your organizational goals.

For many mid-sized employers, that kind of ownership has never felt possible. Some assume they are too small to self-fund, or that the risks and complexity are too high. Captivated Health was created to change that, giving employers the structure and protection to step into self-funding with confidence.

What Makes Captivated Health Different

Captivated Health was built on innovation. While some brokers are just now introducing captives as a “new” idea, Borislow has been leading in this space for more than a decade. We developed industry-specific captives that bring together like-sized employers facing similar challenges.

Joining Captivated Health means more than gaining control of your health plan. It means joining a community of peers who share your world and your goals. The captive model provides an added layer of protection while opening the door to all the advantages of being self-funded.

Why Mid-Sized Employers Are a Perfect Fit

Mid-sized employers are often too small for certain solutions and not large enough to self-fund on their own. Captivated Health bridges that gap by providing access to advanced tools like data analytics, risk management, and custom plan design, all with cost containment at the center.

For CFOs and HR leaders, the model creates alignment. Financial strategy, HR priorities, and organizational goals move in sync, so recruitment, retention, cost control, and employee wellbeing become part of one coordinated approach.

Clearing Up Misconceptions

There are still misunderstandings about captives. Some worry they are too risky or too complex. Others think it will require additional staff or create more work. The reality is different. With Captivated Health, employers are supported by a dedicated team from the first conversation through implementation and beyond.

This is not a one-time transaction. It is a long-term partnership built to deliver sustainable results. Some of the most rewarding moments come when a CFO or HR partner learns there will be no rate increase for the year. Even better is when they share that news with employees. We have clients who have gone years without increases, and some have even provided premium holidays back to their teams.

Looking Ahead

Innovation is part of Borislow’s DNA, and Captivated Health is just one example of how we put it into practice. We are introducing solutions like AI-driven member support and direct primary care, with the goal of staying years ahead of where the market is going so our clients can stay ahead too.

At its core, Captivated Health is about empowerment, strategy, and collaboration. It gives employers true ownership of their health plan, shifting them from reactive renewal decisions to proactive strategies that strengthen both the bottom line and the employee experience. Every decision is data-driven, tailored to organizational goals, and built to support growth while managing risk. And because Captivated Health is also a community, employers gain accountability, shared learning, and stronger outcomes.

Captivated Health was designed to help employers step off the renewal hamster wheel and take control of their benefits future. If you are a mid-sized employer and your broker has never raised a captive solution, that is a red flag. You deserve a partner who will help you explore every option and guide you to the best fit for your people and your goals. At Borislow, that is exactly what we do.

I’ve worked with Borislow Insurance for nearly three decades. Since 2008, I’ve focused almost exclusively on educational institutions, supporting both private and public schools across New England. While this specialization wasn’t something I set out to pursue initially, over time it has become a passion. Working with schools, especially private ones, means working with some of the kindest, most appreciative clients I’ve ever encountered. These are institutions that deeply care about their employees, and that care is reflected in how they approach benefits.

Designing and delivering employee benefits in education is complex. Unlike corporate clients who operate year-round, most faculty follow a nine-month schedule. That compressed calendar means there’s less time to communicate plan changes, answer questions, and manage enrollment. Many private school faculty also live on campus and receive housing and meals as part of their compensation. While these are valuable benefits, they do not show up in salary calculations, which can create discrepancies when benefits like disability coverage are tied solely to income.

In the public-school space, unions add another layer of structure. Changes to benefit offerings must be negotiated, approved, and voted on. There is also a financial impact. Districts facing double-digit renewal increases may need to appeal to taxpayers for funding, which introduces additional constraints.

Despite facing benefits challenges, schools have made strategic progress. Health Savings Accounts are one area where both public and private institutions have embraced meaningful change. Most of our clients offer HSA-eligible plans, and private schools are more often willing to contribute directly to employee accounts. This not only enhances the value of the plan but also opens the door to long-term financial wellness. I often speak to employers and employees about HSAs not just as a way to cover deductibles but as a powerful retirement savings tool.

One of the more common conversations I have with school clients is around benchmarking. In private education, schools are continually comparing their benefits to those of peer institutions. Many feel strong pressure to remain competitive in order to attract top faculty. This has led to extremely rich benefits packages, which are highly valued by employees. However, those packages can make cost containment difficult. If premiums rise significantly, schools may be hesitant to reduce benefits for fear it will be perceived as a loss, even if their plan remains generous by broader market standards.

We work closely with schools to help them view their offerings holistically. When one school felt they were falling behind on dental coverage, we encouraged their HR team to consider the full picture, which includes medical contributions, disability coverage, retirement, and other benefits. Once that context was laid out, it became clear their total package remained very strong.

There have also been cases where we helped schools reconsider their purchasing strategy. One public school district we work with originally purchased benefits independently, then joined the state’s group purchasing plan during a period of high renewals. Several years later, we helped them exit the group and return to direct purchasing, where they have since seen much better outcomes. Another school in Vermont followed a similar path this year and reported a positive shift just six months in. These decisions required careful timing, analysis, and collaboration, but the results were worth it.

Every school is different, which is part of what makes this work so fulfilling. We do not take a one-size-fits-all approach. Our role is to listen, assess, and deliver solutions that align with each client’s culture, goals, and financial realities.

Looking ahead, schools will face increasing pressure from rising premium costs. Rates are trending upward again, and for institutions with long-standing generous plans, managing those increases will take strategy and careful planning.

Even with those pressures, I continue to believe that schools are among the most purpose-driven clients we serve. They focus on community, care deeply about doing right by their employees, and strive to offer benefits that reflect those values. At Borislow, we are proud to stand beside them as long-term partners in their success.

When most people think of compliance, their first thought is often that it’s just a legal requirement, a box we have to check. But that’s selling it a bit short. The truth is, compliance is much more than that. It’s a strategic choice, a way to manage risk, protect your business, and build trust within your organization.

Compliance Is About Choices, Not Just Rules

What makes compliance truly strategic is the element of choice. Employers aren’t just reacting to a set of regulations; they’re making decisions about how they want to run their business, how they want to support their employees, and ultimately, what kind of company they want to be.

Take the Affordable Care Act (ACA) as a prime example. When the ACA rolled out, the conversation wasn’t just about penalties for noncompliance, but the choices companies made to manage those penalties. CFOs understood that it was ultimately their call. They could decide how much risk they were willing to take, and how to design their plans strategically. That’s where compliance shifts from being a headache to a tool for risk management.

The Biggest Myth: “Somebody Else Is Handling It”

One of the most persistent misconceptions I encounter is employers thinking, “I don’t have to worry about this. Somebody else is handling compliance.” This is especially common with the rise of self-funded plans, where employers transition away from fully insured models. But the buck stops with the plan sponsor: the employer. No matter your plan type, the responsibility for compliance ultimately falls on you. That’s a tough pill for many to swallow, but it’s critical to understand—because nobody else is going to do it for you.

Guiding, Educating, and Simplifying the Process

That’s where Borislow comes in. My role, and the role of our compliance team, is to be teachers and guides. Compliance can be overwhelming, especially since the regulations are complex and constantly evolving. My job is to break it down, to make it clear and manageable.

We provide drafts of the necessary disclosures and documents to employers, we educate them about deadlines and what’s required, and we simplify the steps. But at the end of the day, it’s the employer who must finish the job, distributing notices and making sure employees receive what they need.

When compliance is done right, it’s about clearly sharing with employees what benefits are available, how processes work, and what to expect in various situations, like FMLA leave or newborn enrollment deadlines. This transparency creates peace of mind for employees.

Time to Get Your House in Order

With recent federal government staffing changes and fewer resources issuing guidance, it’s a good moment to take a pause. Now is the time for employers to get their compliance foundation solid and prepare for changes that might come in 2026. Use this “quiet period” to educate yourself, shore up your processes, and reduce risk.

Seizing the Opportunity

Compliance often lands on the HR team’s plate, and HR already juggles a million responsibilities. Compliance can feel like just one more thing slowing everything down. But usually, that feeling comes from not knowing what you don’t know. Once you have a partner that educates, guides, and reminds you of deadlines, compliance doesn’t have to be a time drain.

At Borislow, we’re here to simplify that journey, helping employers navigate compliance thoughtfully and confidently. Because at the end of the day, compliance done right isn’t just paperwork; it’s peace of mind.

When most people hear the word compliance, it often triggers thoughts of burdensome rules, endless paperwork, and last-minute scrambling to avoid penalties. I wouldn’t blame you for thinking that way, either. But hear me out: what if we looked at it differently? What if, instead of thinking of compliance as a box to check or a hurdle to jump, we reframed it as regulatory alignment—a proactive, strategic approach that can actually drive your business forward?

That’s how I think about compliance. Not just as something you do to “stay legal,” but as a foundational part of your benefit strategy and company culture. It’s about how you align your plan and your processes with regulatory guidelines from the very beginning, not as an afterthought. It might not remove all the stress of those burdensome rules, but it certainly helps put you in a proactive mindset to make compliance count.

Compliance Isn’t Just About Following the Rules. It’s About Strategic Alignment.

When I think of compliance, I think of it more as regulatory alignment. When you’re developing your overall plan strategy for your company, it’s really about asking yourself: How am I going to align with the regulations, rather than simply being in compliance with them?

The answer (or answers) to that question present a number of strategic opportunities. You can be 100% compliant by following the rules conservatively, but you can also take some calculated risks depending on your company’s goals and risk tolerance. It’s all about protecting your bottom line, being attractive to employees, and retaining your talent.

Thinking about compliance as part of your benefit strategy from the start makes the entire process smoother and more efficient. Instead of building your plan first and then scrambling to fix compliance issues later, you bake regulatory alignment into the foundation of your decisions. This approach makes the development and operation of your benefits streamlined, strategic, and sets you up for greater chances of success.

Compliance’s Role in Recruitment, Retention, and Culture

Regulatory alignment goes beyond a legal requirement. While that’s undeniably an important part of it, regulatory alignment also reflects your company values. When you build a competitive benefits strategy aligned with regulations, it builds trust and morale in turn. It signals transparency and shows that you genuinely want to provide the best for your employees.

And keep in mind the growing need for benefits regulatory literacy, understanding how plans like HSAs work within regulatory rules, who can contribute, and when funds can be used. When employers know this, they can better educate their workforce so everyone maximizes their benefits.

Changing the Conversation

Compliance can be a scary word, and that’s understandable. Just hearing it can make many people want to head for the hills. But when you think of it as regulatory alignment, it sounds a lot nicer, doesn’t it?

My advice to business leaders is simple: Think about compliance first, not last. Instead of “Oh, this is something I have to do,” flip the script. See it as a helpful guide, a set of guardrails that help you make smart decisions from the beginning. This mindset doesn’t just make your job easier; it also supports your company’s overall strategy and values.

At Borislow Insurance, we’re passionate about helping employers reframe compliance as a positive, strategic driver, not just a box to check. When regulatory alignment is baked into your benefit strategy, it’s not just about avoiding penalties. It’s about empowering your business and your people to succeed.