Minneapolis, Minnesota Sep 15, 2026 (Issuewire.com) - Roll With Paid., a payroll, human resources and employer-of-record (EOR) company, announced its launch today, serving employers in regulated and high-risk industries that conventional payroll and HR providers routinely turn away.
The company is majority-owned and co-led by Managing Member Jen Williams, a member of the Sisseton-Wahpeton Oyate, whose background spans nearly two decades across HR, management, public relations and marketing. It was founded by Leah Kollross, who spent 18 years in HR and payroll before building the infrastructure partner she could not find for her own clients. Its capabilities include payroll processing and tax filing, workers' compensation coverage, unemployment insurance administration, onboarding and I-9 documentation, benefits access, and ongoing HR support, operating behind the scenes while clients retain full authority over hiring, management and day-to-day operations.
The gap the company is entering is a practical one rather than a legal one. Employers in sectors carrying elevated workers' compensation classifications, unusual regulatory exposure, or high turnover are lawful businesses with lawful workforces, but many national payroll platforms and insurance carriers decline entire categories on risk-appetite grounds rather than on the merits of the individual business. Operators are left to assemble employment infrastructure from parts, or to run it by hand.
That falls hardest on the smallest teams, at exactly the moment Minnesota's employment obligations have expanded. Minnesota employers now administer earned sick and safe time, a state Paid Leave program that began collecting premiums on January 1, 2026, pay transparency requirements in job postings, and workers' compensation classification that shifts as roles change inside a growing operation. Most of these obligations attach at the first employee, with no small-business exemption.
"We built this for the businesses that got told no," said Leah Kollross, Founder of Roll With Paid. "Not because they did anything wrong, but because someone's risk model had a box that didn't fit them. These are real companies with real employees who deserve an accurate paycheck and a clean W-2. That shouldn't depend on whether a national platform feels like taking the account."
The company launches with a dedicated tribal relations practice supporting tribally chartered enterprises, Indigenous-owned businesses, and employers operating in Indian Country, led by Williams.
"Tribal enterprises and Indigenous-owned businesses have been building real operations for a long time, often with fewer partners willing to work with them," said Jen Williams, Managing Member of Roll With Paid. "Payroll is where a company's stated values become verifiable. An employer can say it treats people well, but the pay stub either backs that up or it doesn't. We want that never to be in question, and we want tribal members and Indigenous-owned businesses to have a real partner rather than a workaround."
Roll With Paid. is based in Minnesota, with expertise in state-specific requirements including the Wage Theft Prevention Act, Paid Leave and tip-handling rules, and infrastructure that supports multi-state operations. Pricing is structured by workers' compensation classification code and gross wages rather than a single blended rate, and the company publishes a comparison of the employer-of-record model against conventional payroll software.
The company also publishes Roll Call., a newsletter covering payroll, HR and regulatory developments for employers in high-risk industries.
Businesses can get started or contact the company directly.
About Roll With Paid.
Roll With Paid. is a Minnesota-based payroll, HR and employer-of-record company serving employers in regulated and high-risk industries, including hospitality, food service, manufacturing and other sectors where conventional providers limit their appetite. The company is majority-owned by Managing Member Jen Williams, a member of the Sisseton-Wahpeton Oyate. Roll With Paid. manages payroll execution, tax filing, workers' compensation, unemployment administration, benefits and employment compliance so its clients can focus on running their businesses, and maintains a tribal relations practice supporting Indigenous-owned and tribally chartered enterprises. Roll With Paid. is not a law firm and does not provide legal or tax advice.
Media Contact
Roll With Paid info@rollwithpaid.com https://rollwithpaid.com
