Built to carry the responsibility behind employment.
Roll With Paid. is a payroll, HR, and employer-of-record company built for businesses operating in complex, regulated, and high-risk environments. We sit behind the scenes, managing payroll execution, compliance, benefits administration, and employment risk, so our clients don’t have to assemble or maintain those systems themselves.
Waciŋyaŋ. Our role is simple: create stability where employment complexity exists, and protect businesses from the operational breakdowns that slow growth or expose risk.
Designed to work quietly. Built to work flawlessly.
Roll With Paid. operates as the employment layer beneath your business. While you lead your team and manage day-to-day operations, our systems handle what happens behind the scenes, accurately, compliantly, and consistently.
Built for Risk
Designed for regulated and high-risk industries where compliance mistakes carry real consequences.
Authority Stays With You
You hire, manage, and lead your employees. Roll With Paid. handles the infrastructure behind them.
Protection at Scale
As your workforce grows, our systems adapt, without adding administrative burden to your team.
Minnesota-Based, Nationally Capable
Rooted in Minnesota’s cannabis and hospitality industries, with the infrastructure to support multi-state operations.
Our mission is simple: make employment easier to manage and harder to get wrong.
Roll With Paid. exists to take on the responsibility behind employment, from payroll and compliance to benefits and risk, so businesses can operate with confidence, clarity, and control as they grow.
We believe workers deserve to be treated as partners, not liabilities. And we believe the businesses that employ them deserve a real partner, not a software platform.
For the businesses they said no to, and the workers they overlooked.
Meet Your HR + Payroll Team
Roll With Paid. is led by professionals with deep experience in payroll, HR, and regulated industries.
Leah Kollross
Founder18+ years of HR and payroll experience, including extensive work in cannabis and high-risk industries. Leah built Roll With Paid. to give operators the infrastructure partner she never had access to herself.
Jen Williams
Managing Member, Roll With Paid.Spanning nearly two decades across HR, management, PR, and marketing, Jen Williams brings a rare combination of people skills and communications instincts to her work. As a proud member of the Sisseton-Wahpeton Oyate, she is committed to building ethical business practices that create real opportunity for tribal members and Indigenous-owned businesses.
“We remember where you came from, and we’re building where you’re going.”
For businesses that have grown through grit and are ready for infrastructure to match.