IT service management company Square is now offering benefits for small and mid-sized businesses as part of its Square Payroll app, the company’s cloud-based payroll system.
Square introduced health insurance, retirement savings, pretax spending and workers compensation benefits to the app in November. The company has partnered with benefits providers including small business health insurance company SimplyInsured, retirement savings offering Guideline 401(k), digital insurance platform AP Intego and pretax savings provider Alice, to offer benefits to employers.
Caroline Hollis, head of Square Payroll, says the company is hoping to give “small businesses access to ‘big company’ benefits.”
“We’re empowering businesses to provide their employees a comprehensive set of benefits and the financial security that comes with having them,” Hollis adds.

In a statement, a Square representative says the platform gives small businesses access to benefits that have historically only be available for larger businesses. Some small business cannot afford to give employees benefits, either because of the size of their business or the cost of the benefits, the company adds.
Across the board, there has been some movement in the HR technology space to increase access to benefits and HR services for small and mid-sized companies. San-Francisco based startup
“Options we looked at before had employee minimums that prevented us from qualifying, but with Square Payroll the benefit plans are designed to meet the needs of businesses my size,” says Shatisha Wilson, owner of Wilson’s Garden of Hope, a play therapy and counseling center in Augusta, Georgia who offers Square Payroll benefits to her employees.
A Square representative says employers in retail, restaurants and professional services are using the platform, but did not name specific companies. Square Payroll costs $29 per month plus $5 per employee and contractor paid. The company’s contractor only option is $5 per contractor per month with no base fee. Square says the benefits pricing varies based on the type selected.