An Expert Interview with Kyle Janssens, Senior Manager, Yearli
Year-end wage and information reporting is one of the most deadline-driven compliance obligations a business faces. Whether you are filing ten W-2s or thousands of 1099s, the platform you choose determines whether that process goes smoothly or falls apart at the worst possible moment.
At Voted Number One, we look at the qualities that make business products and services stand out in crowded, high-stakes categories. For filing platforms, reliability is the difference between a clean filing season and a costly compliance problem.
We sat down with Kyle Janssens, Senior Manager at Yearli, to understand what separates a genuinely reliable W-2, 1099, and 1095 filing platform from one that simply checks a box.
Q1: When businesses are evaluating W-2, 1099, and 1095 filing platforms, what is the single most important reliability factor they tend to overlook?
Kyle: I’d point to how well the pieces actually work together, rather than just existing. Almost every platform on the market handles federal filing, state filing, and recipient delivery in some form, that part isn’t the differentiator anymore. What varies a lot more is whether those pieces are built into one platform or stitched together, whether recipient copies actually go out on time, whether state filing is automatic or something you have to configure state-by-state yourself. Businesses tend to confirm “yes, it does federal, state, and recipient” and stop there, without checking how much manual work sits between those three boxes.
Q2: The W-2, 1099, and 1095 filing window is extremely short. How does a reliable platform perform under that kind of deadline pressure?
Kyle: This is where platforms really separate from each other. Most businesses aren’t filing steadily throughout the year, they’re filing in a tight window in January, right alongside everyone else who’s doing the same thing at the same time. That’s exactly when errors are most likely to happen and least likely to get caught in time. Something that works fine on a quiet day in March can feel very different in the last two weeks of January, when there’s no room left to redo anything.
Import has to be fast. Businesses shouldn’t be rebuilding their data by hand every year just because their format doesn’t match what the platform expects. Status visibility matters too, if a form comes back rejected, you need to know immediately, not after the deadline’s passed. And support has to be an actual person, quickly, because some problems can’t sit in a ticket queue during the last week of January.
With clean data and the right setup on the front end, what used to take a business a full week can come down to an afternoon.
Q3: TIN matching is a term that comes up often in 1099 filing. How should businesses think about it, and why does it matter for platform reliability?
Kyle: Here’s the thing about TIN matching, a name-and-number mismatch on a 1099 is one of the most common reasons the IRS flags a filing. Doesn’t matter how carefully the business captured the vendor’s information. If it doesn’t match IRS records, they’re exposed. TIN matching catches that before submission instead of after, when you’re dealing with a notice instead of a keystroke. It’s one of the more underestimated reliability factors out there, and one of the clearest places platforms actually differ. It shouldn’t be reserved for the biggest filers either. No one should be filing blind, whatever their volume.
Q4: The W-2, 1099, and 1095 filing market is crowded with options. What actually distinguishes Yearli from the other platforms businesses will come across?
Kyle: It’s a crowded space: you have payroll providers with filing bolted on, standalone filing tools, big-name providers, all going after the same customers. Most of them can get a basic form submitted. Where it gets more complicated is everything around that.
Pricing is a good example. The rate you see up front often isn’t the rate you end up paying, state filing, print and mail, recipient delivery can each come as separate line items, and those add up fast once you’re filing any real volume. It’s worth asking what’s actually included before comparing two prices side by side.
Fit matters too. A five-person company and a firm managing 200 clients in January need genuinely different things. And there’s category experience: this is a narrow, rules-heavy space, and a team that’s dedicated itself to it since 1975 carries a different kind of institutional memory than a general product with a filing module attached.
Q5: What is the most common mistake businesses make when choosing a year-end filing platform, and how does it cost them?
Kyle: I think it’s assuming the differences between platforms won’t matter until they do. On paper, most options look similar, they all submit forms, they all say they cover federal and state. But similar isn’t identical, and the gaps tend to show up as confusion more than outright failure: a rejected form nobody caught in time, a status you can’t get a straight answer on, a support request that sits unanswered during the one week you can’t afford that.
None of that shows up on a pricing page. It shows up as time lost, stress during an already stressful few weeks, and in the worst cases, an IRS notice you now have to resolve. The real question to ask upfront isn’t “what does this cost”, it’s “what happens when I’m confused or something doesn’t go as expected.”
Yearli is a web-based W-2, 1099, and 1095 filing platform serving small, medium, and large filers, accountants, and service providers nationwide. Yearli is headquartered in Grand Rapids, MI, with 50 years in wage and information reporting behind it. To explore plans and start filing, visit yearli.com.