Building Stronger School Strategies

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.