Your Team. Our Risk.

Built for the ones who had to build it themselves.

We manage payroll, compliance, risk, benefits, and HR operations under our umbrella — so you stay protected and fully in control of your team. Haŋ, taŋyáŋ yahípi! Roll With Paid. was built for the businesses other providers turned away.

In the News
Bloomberg
Forbes
Yahoo Finance
Star Tribune
FOX 9
5 Eyewitness News
WGN America
Morningstar
Benzinga
Breadstack
High Times
Marijuana Moment
Cultivated
WeedWeek
Hemp Gazette
GreenState
BevNet
NOSH
Brewbound
Nombase
Client Record

What Our Clients Say

High-risk industries need a partner who actually understands them. Here’s what ours say about working with Roll With Paid.

Trusted by cannabis operators, dispensaries, cultivators, and high-risk businesses across Minnesota and beyond.

Earl Giles Drinks Emporium
Natural Harvest
Minnesota Cannabis College
23rd State
LK Holdings Inc.
Gilt Homes
Lantech
Radiant design | build
Client logo
Stay Compliant With Roll With Paid.

Are You Ready for Your Next Compliance Audit? With Roll With Paid., You Already Are.

Cannabis businesses face more scrutiny than any other industry. One missing I-9, a late tax deposit, or a misfiled state form can cost thousands. We handle all compliance behind the scenes — so you stay audit-proof without lifting a finger.

Audit file Reviewed monthly
  • I-9 and E-Verify recordsCurrent
  • Federal and state tax depositsOn time
  • Wage and hour recordsRetained
  • Worker classification reviewPassed
  • State registration filingsActive
Payroll Execution

Payroll Mistakes Are Expensive. We Make Sure They Never Happen.

Late filings, incorrect withholdings, and misclassified employees create IRS notices that cost time and money. Roll With Paid. handles every payroll detail — deposits, filings, amendments, year-end prep — so your business never faces an avoidable penalty.

Filing calendar Handled for you
  • Semi-weekly federal depositScheduled
  • Quarterly 941Filed
  • State unemployment returnsFiled
  • Amendments and correctionsManaged
  • W-2 and year-end prepIn progress
Onboarding

Still Buried in Hiring Paperwork? We Handle Onboarding From Day One.

Most payroll problems don’t start with payroll — they start with everything attached to it. Roll With Paid. manages the full weight of employment under one system built for accuracy, protection, and scale.

New hire: day one 4 min to complete
  • Offer letter issuedSigned
  • Background checkCleared
  • W-4 and state withholdingOn file
  • Direct deposit set upVerified
  • Handbook acknowledgementReceived
Risk Transfer

The Operating Layer Behind Your Workforce.

Partner with Roll With Paid. for immediate business protection and risk mitigation. We help you achieve lower workers’ compensation rates, reduce unemployment tax exposure, minimize legal liabilities, and issue paystubs under our name to protect your brand. This move safeguards your employees against financial discrimination — while securing your business from unnecessary risk.

Where the weight sits Your side / our side
Your business Hiring, management, scheduling, culture, day-to-day decisions.
Your team Reports to you. Follows your policies. Paid on time, every cycle.
Roll With Paid. — the layer underneath Payroll, filings, workers’ comp, unemployment, benefits, claims, compliance.
One System

Everything Employment Requires, Handled in One Place.

From payroll to compliance, benefits to risk management — Roll With Paid. absorbs the complexity of employment so your business runs cleaner, safer, and faster.

01

Built for High-Risk Industries

Traditional payroll companies avoid high-risk sectors. We were built specifically for them.

02

Cannabis-Focused Compliance

We understand state regulations, tax codes, and reporting requirements — so you stay compliant without the stress.

03

Employer of Record Protection

Reduce liability, strengthen compliance, and access benefits through Roll With Paid. as your EOR.

04

Automated Payroll & Tax Filing

Accurate payroll every cycle with automated state and federal tax filing, reporting, and year-end forms.

05

Seamless Employee Onboarding

Fast, compliant onboarding, background checks, and documentation built for regulated industries.

06

Multi-State Hiring Support

Expand confidently with payroll and compliance systems designed for teams operating across multiple states.

07

Workers’ Comp & Unemployment

We manage workers’ compensation coverage and unemployment insurance administration through our EOR model.

08

Time & Attendance Tools

Track hours, manage schedules, and maintain labor-law compliance with integrated workforce tools.

09

Dedicated HR Expertise

Real human support — not a call center. Our team helps with policies, handbooks, employee issues, and compliance questions.

Our Capabilities

Explore What Roll With Paid. Does

We operate behind the scenes — absorbing payroll, compliance, and risk — while you retain full authority over hiring, management, and day-to-day operations.

Hiring

Your Team, Your Call

You recruit, interview, and choose who joins your team. Roll With Paid. supports the process, but the decision is always yours.

HR

HR & Compliance Solutions

Streamline onboarding, documentation, labor-law compliance, and HR administration — so your team stays protected and productive.

EOR

Employer of Record

We handle payroll, filings, claims, benefits, and compliance. The liability shifts to our system — without shifting your authority.

Industry

Cannabis & High-Risk Expertise

We specialize in dispensaries, cultivation sites, and other regulated industries — providing guidance other providers simply can’t.

From the Team

From the Roll With Paid. Team

Stay ahead with the latest on payroll, HR, compliance, and high-risk industries — including cannabis.

“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.

Roll Call.

Compliance changes fast. We send what matters.

Payroll, HR, and regulatory updates for high-risk operators. Once a month, no filler.

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