With businesses now overseeing open enrollment for their workers, many employers admit they’re struggling to find ways to finance and organize increasingly complex benefit plans. Yet rather than decide to simply cut those programs as too costly and laborious to continue, a majority of small business owners are considering turning to outside experts’ help to make them more effective.
Employers’ commitment to benefits, and accompanying awareness that their plans are getting too difficult to operate alone, were two major findings in a recent survey of 759 small businesses by the U.S. Chamber of Commerce (USCC) and JustWorks, an HR tech company. Nearly 70% of participating entrepreneurs said they recognize they need help in running their programs, and “wish they had outside” support in structuring, operating, and budgeting them. That desire for expert third-party assistance stood at 75% among Gen Z and millennial owners, with 64% and 54% of Gen Xers and boomers considering the idea, respectively.
Little wonder so many entrepreneurs are considering outside help in orchestrating benefits programs—especially with annual open enrollment activity underway. In addition to managing the often wide array of options included in many company plans, business owners are also forced to find new budgeting adjustments to fund their rising costs.
Health care insurance is the main example of that. While premium increases to all companies this year are slated to surpass 9%, they’re hitting small businesses particularly hard.
Despite rising costs, owners expand benefit coverage
According to a recent report by the payroll services platform Gusto, employee medical costs to entrepreneurs have surged by 31% since 2022, and now represent $8,743 per worker. Entrepreneurs with staff of two to five people have endured 35% hikes in premiums over the same period, and now pay about 6% more than businesses with 25 to 50 employees.
Yet rather than pull back or eliminate benefit programs, many small business owners have found a variety of hacks to not only maintain their plans, but expand them to more staff members.
Crafty budgeting and financing decisions allowed entrepreneurs surveyed by the USCC to increase health insurance coverage from 41% of workers in the second quarter of 2025 to 46% in Q3 this year. Similarly, paid vacation days increased from 30% to 40% over the same period, while dental and vision plans expanded from 21% to 31% of staff. Retirement programs rose from 22% to 27% of employees participating.
The difficulty of finding ways to free up funds to pay for benefits programs—and the hard decisions necessary to redirect limited finances to staff plans—is one reason why a majority of business owners are considering asking for outside help to manage and operate programs.
Another motive is that many entrepreneurs are interested in using efficiencies gained from expert assistance to expand their support to workers even more.
“I would love to offer programs that help with tuition/student loans, support with homebuying/child college savings, and offset childcare or elderly care costs,” Joanne Sanders, a survey participant and president of Ewise Marketing and Communications in Georgia, told USCC pollsters.
Benefits pay off in better staff productivity and retention
There’s more than altruism behind those generous ambitions. Studies have shown that employee productivity, well-being, and loyalty all tend to strengthen at businesses offering benefit plans.
According to recent data from Lincoln Financial, 74% of “employers who offer voluntary benefits cite positive effects on recruitment, retention, and performance.” That figure rises to 86% at companies providing supplemental accident, critical illness, and hospital indemnity insurance options that often save employees from financial ruin from health calamities.
Despite the difficulties of financing and operating benefit plans, most USCC respondents said they believe what they provide is effective in improving staff lives, finances, and loyalty. Around 80% of small business owners reported their “employees are satisfied with the current offering,” and 57% said staffers “rate their total compensation package as good.”
But with packages growing more complex and costly every year, it’s not surprising most small business owners want outside help to ensure they can keep offering benefits that everyone can afford.
“Health insurance premiums climb nearly every renewal cycle, often outpacing general inflation,” Stevie Straka, vice president of people at the Ann Arbor, Michigan-based cybersecurity company Blumira, said in a report on the USCC survey. “(T)hat forces a tough annual trade-off between absorbing rising costs, shifting more of the burden to employees, or scaling back coverage.”
Those difficult decisions are why more employees now involved in or preparing for open enrollment may find their bosses getting expert help organizing and managing workplace benefit programs—and keep them running well into the future.
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This article originally appeared on Fast Company’s sister website, Inc.com.
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