Hospitality
Tip credits, split shifts and overtime that changes with the week.
Built for High-Risk Industries
Traditional payroll companies avoid high-risk sectors. We were built specifically for them.
In the News
Statement of Earnings
Period 04
- Employees paid
- 142
- Federal deposit
- Filed on time
- State filings
- 4 states clear
- I-9 verification
- Complete
- Workers' comp
- Active
Handled by
Roll With Paid.
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.
Roll With Paid. came in during the hardest year this business has had and took the people side of it off my plate completely. Our costs are down, our employment practices are in better shape than they have ever been, and every decision we have made about our team has been handled with real care. I would put them in front of any operator in this industry.
Nick Kosevich
CEO and Partner, Earl Giles
Compliance was keeping me up at night. Between state filings, I-9s, and workers’ comp, there were too many moving parts. Roll With Paid. consolidated all of it. We haven’t had a single late filing since we made the switch.
We didn’t need a full-time HR person, but we absolutely needed HR expertise. Roll With Paid.’s fractional support gave us exactly that: a handbook, an onboarding process, termination guidance. All without the overhead of a hire we weren’t ready for.
Our headcount swings dramatically with the seasons. Most payroll companies don’t know how to handle that, so we were constantly scrambling. Roll With Paid. built a system around how we actually operate, not how they wanted us to operate.
Honestly, I didn’t even know half of what I was missing until Roll With Paid. came in and pointed it out. Our onboarding was a mess, we had no real handbook, and nobody had ever explained our benefits properly to staff. It wasn’t dramatic. It was just quietly broken. Now it’s not.
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
- 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 and year-end prep. Your business never faces an avoidable penalty.
Filing calendar
- 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
- 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 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.
Software or Employer
Same tools. Different name on the paperwork.
Payroll software and an employer of record both run your payroll, and the screens look much the same. The difference shows up on the day something goes wrong, in whose name is on the filing.
| Item | Payroll software | Roll With Paid. |
|---|---|---|
| Named W-2 employer | Your business | Roll With Paid. |
| Workers’ compensation | Your own policy, at your own experience mod | Included in our rate, on our policy |
| Unemployment insurance | Your account and your experience rating | Our account and our rating |
| Employment practices and general liability | Sourced separately by you | Included |
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
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.
In Detail
The whole list, not the highlights.
Every provider says they handle HR. Here is what that means here, named line by line, so you can check it against the list you are keeping yourself today.
Human Resources
- Compliance
- Best practices
- Shared liability
- Risk mitigation
- Training
- Employee handbook
- Policies and procedures
- Job descriptions
- Employment practices liability
Payroll Administration
- Accurate, timely and compliant payroll
- Direct deposit
- Federal and state payroll
- Tax computation and government filings
- PTO accrual management
- W-2s
- Records broken out by role and department for 280E allocation
Insurance Services
- Multiple plan access
- Health, dental, vision and EPLI
- Employee attraction and retention
- Billing reconciliation
- Administration
- Open enrollment
- Broker of record on client plans
- 401(k)
Workers’ Compensation
- Insurance provision
- Certificates of insurance
- Claims management
- Return-to-work programs
- Accident investigations
- Cost containment
- Compliance
- Annual audit
- Administration
Workplace Safety
- Injury and illness prevention programs
- Facility inspections
- Safety manuals
- Pre-employment screenings
- Employee and employer training
- Cost containment
- Compliance
Technology (HRIS)
- Electronic onboarding
- Time and attendance
- Employee self-service portal
- Integrated payroll system
- Payroll and management reporting
- CRM
- Applicant tracking system
- Performance management system
- Hiring process manager
- Document and case management
Benefits and 401(k) administration are included; employer contributions remain yours. Roll With Paid. is not a law firm or an accounting firm and does not provide legal or tax advice.
Case Studies
What this looks like in a real business.
Four industries where the payroll rules are tangled in a different way each time, and what changed once somebody else carried them.
Cannabis & Hemp
Federal tax under 280E, state rules amended since they were written, and most providers saying no.
Construction & Trades
Prevailing wage, certified payroll and the class codes that decide what a crew costs to staff.
Tribal Enterprises
Sovereign nation governance, state regulation and federal law, none of them agreeing.
Roll Call.
From the Roll With Paid. Team
Stay ahead with the latest on payroll, HR, compliance, and high-risk industries, including cannabis.
Cannabis Employee Handbook: What to Include in 2026
What a cannabis employee handbook must cover: wage and hour rules, drug testing, safety, discipline and state differences, with real regulatory citations.
Read More
E-Verify vs. I-9: What Each Does and Which You Need
E-Verify and Form I-9 are not alternatives. See what each does, who must use them, key deadlines, and how paper vs. electronic I-9 fits…
Read More
Does the DEA Register Dual Medical and Recreational Cannabis Licensees?
The DEA is refusing federal registration to dual-license cannabis operators, Minnesota included. See who qualifies, what it means for payroll and taxes, and what…
Read More
Common Questions
The questions we get asked first.
What changes, what does not, and what it costs. If yours is not here, the full list is one click away, and you can always just ask us.
Do I still control my employees?
Yes. You retain full authority over hiring, management, scheduling, performance, and termination decisions. Roll With Paid. operates behind the scenes, handling payroll, compliance, benefits, and employment administration, without interfering in day-to-day operations.
What does it cost?
Two parts. A service rate applied to gross wages, quoted by workers’ compensation classification code because a budtender and a grower do not carry the same risk, and an optional flat monthly HR retainer based on headcount. The rate sits on top of wages rather than replacing them, so a 16.94% rate on a $10,000 payroll is $1,694. Our pricing page shows illustrative rates by code and a calculator that separates the two. Your own rate comes after we have seen your payroll history and census.
Will my employees know anything has changed?
No. Your employees continue to report to you, follow your policies, and operate within your culture. Roll With Paid. supports the administrative side of employment without disrupting your internal operations or team dynamics.
Are you only in Minnesota?
We’re Minnesota-based with deep expertise in MN-specific regulations, but our infrastructure supports multi-state operations. If you’re operating or expanding beyond Minnesota, we can support that.
How do we get started?
After an initial call, Roll With Paid. handles the transition of payroll and employment administration into our system, minimizing disruption while ensuring accuracy and compliance from day one. Most clients are fully onboarded within one to two pay cycles.
“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.