Paying someone to fix it - only to realize they have one of their own.
In the world of off-duty law enforcement work, there’s no shortage of “solutions” or “management” firms claiming to fix a real problem: “Who protects the officer when they’re not technically on duty but still doing the job?”
The gap is real. Too many officers assume they’re covered. Too many agencies hope the hiring business is on the hook. Too many cities find out the hard way that no one is.
Seeing our growth and the demand for structure and accountability, some vendors stepped into the space, offering full-service solutions. For W-2 agencies, that’s fine. They can pair managed services with internal payroll, benefits, and oversight because the employer relationship is already established. These agencies have a compliance gap - but not a classification one. They can go back to sleep on that issue.
But here’s where it gets dangerous:
Some vendors have extended that same full-service model to 1099 contractor programs - where the officers are not W-2 employees, and the vendor is issuing payments directly. Now, you’ve got a square peg being hammered into a round hole.
That’s where the real blind spot forms.
If It Walks Like an Employee…
Let’s say you start offering officers things like guaranteed pay, subsidized insurance, shift limits, centralized supervision, and standardized procedures. Sounds organized, right?
But now ask: does that sound like a contractor… or an employee?
Truth is, most off-duty officers get to choose the jobs they work - when, where, and if. But as soon as a third party starts setting maximum hours, issuing mandatory rules, negotiating benefits on their behalf, and promising how or when they’ll get paid… well, congratulations. You’ve just crossed into “control” territory. And in the eyes of the Department of Labor, control = employment.
Now that officer you were trying to protect? They’re no longer a 1099. And you’re potentially on the hook for:
Retroactive overtime pay
Pension contributions
Payroll taxes
Ongoing benefit obligations
The officer you were trying to protect? Now a legal liability. And the vendor you hired to reduce your risk? They just handed you a compliance landmine.
The Old “New” Way Doesn’t Work
At RollKall, we have a heart for service. We aren’t businessmen who just saw an opportunity to build a service company; we’re actually cops who worked these jobs to pay our bills. So when those competitors started offering Workers' Compensation insurance for these officers, we agreed that they deserved to be protected.
Like them, we tried to wedge traditional workers’ comp into a system it wasn’t built for. After all, it seemed like the responsible move.
But we learned the hard way: Workers' comp only works when there’s a direct employer-employee relationship or when a contractor is under the insured's direct control. That’s not the reality of off-duty law enforcement. And trying to force it? Square peg + round hole again = broken program.
So we did the hard thing: we stopped duct-taping a legacy solution to a modern model and built something purpose-built instead.
RollKall Workers’ Protection: Built for This. Not Bent to Fit.
We partnered with an A+ rated insurance carrier and developed the first policy of its kind - coverage designed specifically for public safety professionals working through our platform. It protects them without reclassifying them. It covers risk without handing agencies unexpected liabilities. And it doesn’t require pretending your officers now work for your software vendor.
No loopholes. No fine print. No new blind spots.
Let’s Not Pretend Control Is Risk-Free
Yes, oversight matters. Yes, agencies should enforce fatigue rules and prevent conflicts of interest. Yes, there should be accountability when public resources are used for private work.
But if a solution exerts too much control - especially in areas like scheduling, compensation, or benefits - then it’s not a solution anymore.
It’s a liability accelerator.
And the more control you have, the closer that officer’s independent contractor status starts looking like a W-2 employment issue for you.
So next time a vendor says, “Trust us, we’ll take care of everything,” just check your mirrors. Because there’s a difference between managing risk and reclassifying it.
We Didn’t Just Spot the Problem. We Solved It.
We’re not perfect, but we’re proud of what we’ve built - and who we built it for. We didn’t chase convenience. We chased compliance. We didn’t prioritize control. We prioritized clarity. And we didn’t build a system to own officers. We built one to empower them.
Because if you're going to fix a blind spot, you'd better not bring one of your own.
That’s not leadership. That’s just driving with your eyes closed.
—
Chris White
Founder, RollKall Technologies