Mastering Payment Reporting: Why CPRS Certification Matters with Jason Dinesen

Staying compliant with payment reporting regulations is more critical than ever – so how can finance professionals ensure they have the knowledge and skills to do it right? In this episode, IOFM Content Manager Grace Chlosta sits down with returning guest and expert trainer Jason Dinesen to discuss the Certified Payment Reporting Specialist (CPRS) certification.

Jason breaks down why this certification is essential for finance professionals, what attendees can expect from the CPRS training at the upcoming IOFM Spring Conference & Expo, and how certification can enhance career growth and organizational compliance. Whether you're considering certification or just looking to sharpen your expertise, this episode is packed with valuable insights.

Tune in now to learn how CPRS certification can help you stay ahead in the ever-evolving world of payment reporting!

Jason Dinesen

Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason is the founder of Dinesen Tax & Accounting, P.C. and Dinesen Tax Advisory, LLC in the tax and accounting world. He also is founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals, to podcast production to radio and journalism content. 

Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics. Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe's in West Des Moines, Iowa. He still teaches on 1099s and around 30 other tax topics.

Grace Chlosta
Content Manager, IOFM

Grace Chlosta joined the Institute of Finance & Management (IOFM) in 2022 in a new role for the team as the Content Manager. She is responsible for the planning, organization, development, and implementation of all the content for IOFM’s digital products and (virtual and in-person) events. Grace is committed to ensuring that IOFM’s content stays timely, relevant, and actionable for all financial operations professionals, and works closely with a team of content developers, industry leaders, and subject matter experts to guarantee this happens.

Transcription

Grace Chlosta: Welcome to the IOFM podcast. This is a podcast for accounts payable and accounts receivable professionals who want to stay in the know with current AP and AR trends and ideas. We'll be interviewing professionals in this space on a wide variety of subjects, including automation, artificial intelligence, career growth, compliance, leadership, and much more.

Today, we'll be interviewing Jason Dinesen. Jason is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason is the founder of Dinesen Tax & Accounting P.C., and Dinesen Tax Advisory, LLC, in the tax and accounting world. He's also the founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing-education programs for accountants and tax professionals to podcast production to radio and journalism content.

00:01:00

He'll be interviewed by me, Grace Chlosta. I joined the Institute of Finance & Management in 2022 in a new role for our team as the Content Manager. I'm responsible for the planning, organization, development, and implementation of all the content for IOFM's digital products and virtual and in-person events. I'm committed to ensuring that IOFM's content stays timely, relevant, and actionable for all financial operations professionals. I work with a team of content developers, industry leaders, and subject-matter experts to guarantee that this happens. 

Hey, Jason, how are you? 

Jason Dinesen: I'm good, Grace. How are you?

Grace Chlosta: I'm good. Super excited to have you back on the IOFM podcast. As many of you know, Jason is our tax reporting compliance expert, but he's also our Certified Payment Reporting Specialist (or CPRS) trainer at IOFM's upcoming spring conference and expo. So if you work in AP or finance, you know just how critical it is to really stay on top of everything with compliance regulations, everything going on there, and that's exactly where the CPRS certification really comes in.

00:02:02

In today's episode, Jason and I will be diving into why this certification matter, what you can expect from the training at our spring event, and really how it can help you and your organization stay compliant and ahead of the curve going forward. So, Jason, just to start us off, could you just give us a brief overview of CPRS, and really who the idea candidate would be for that certification? 

Jason Dinesen: Yeah. So CPRS is the 1099 certification, basically, and it is for anybody who has a role in the 1099 process, in particular if you're kind of the point person in your organization for 1099s. I know the writeup to CPRS says it's designed for those responsible for compliant 1099 reporting to vendors and the IRS. If that's you, if you're the person dealing with getting those 1099s prepared or pulling the information and determining what needs [to be] reported, who it needs to be sent to, etc., etc., that's really what this program does is it makes you kind of your organization's expert, basically, on 1099s.

00:03:25                     

Grace Chlosta: Exactly, Jason. Yeah, that's right on the money. It's just really for anyone who's looking to stay compliant, who is responsible for all of that at the company. So you hit the nail on the head there. Why do you think it's important for professionals, if they're going to their boss and they're saying, "I really think this is important for us," what could they say to really kind of help them get the A-okay to go ahead? Why do you think that this is a good investment for the company?

00:03:54                     

Jason Dinesen: Well, there's a few things that I say in that regard. One is the penalty amounts go up each year for 1099 filings, and even if you file something on time and you think that you've met the filing deadline, if there's mistakes in what you filed, the IRS could actually penalize you because the rule says that a complete and accurate form must be filed by the deadline. So if your form isn't accurate, even if you filed it by the deadline, you could potentially be penalized.

This stuff is hard. I know, Grace, you (kind of by osmosis, I think) have come across some 1099 stuff where like, "Wow." 

Grace Chlosta: Yeah.

Jason Dinesen: You see "Ask the Expert."

Grace Chlosta: I was going to say, [with] "Ask the Expert," there has been some very complex questioning coming through the inbox, especially in the last couple of months, where there are some unique problems out there. There's a lot – a lot – going on.

00:05:00                     

Jason Dinesen: That is for sure. And what I always tell people – I'm very honest about these things. I learn new things about 1099s. Maybe not every day and not every week, but every now and then I come across something, especially from the "Ask the Expert" questions, where it's like, "You know, I've never thought of that," and I will dig deep on something and it's like, I learned something new.

I think that, [in] this program, we cover all the ins and outs of 1099s, and a little bit of 1042-S. There's just a segment of 1042-S. Most of it's on 1099 issues, but we cover all of those ins and outs. One of the things that I said when I taught this in Las Vegas last fall, at the very beginning, is: When you deal with this stuff and you realize just how complicated it is –

00:06:04

And like I say, I learn new things periodically, too, so it's not so much that you're going to know every single thing that there is to know about 1099s, because I don't know that that's possible, but you learn where to look for the answers, whether it's the Master Guides that IOFM has, which are excellent things, or the regulations, various pieces of IRS guidance, even IRS publications or whatever, you learn where to go to look up the answer and find the answer. 

00:06:51

I think that's a big part of what CPRS does, too, is it lets you know… How do I want to say it? You start learning to know what you don't know and how to find the answers to those things. 

Grace Chlosta: Yeah, there's a lot out there. Even if you just look at the Master Guides, they're really in-depth, long pieces of text. So I guess you're right, just learning where to look, how to use them. You might have them, but where do you even begin to look for an answer that you might need within those, so I think that's a really great point.

Jason Dinesen: Yeah, exactly.

Grace Chlosta: And I think that, too, now that you're answering all of these "Ask the Expert" questions, and like you said, if you're getting not stumped by some but you're learning new things as you're answering, those are all things that can always be incorporated into CPRS, and that's a benefit, I would say, of live, in-person certification as opposed to any other options that we might have. I think that being able to be in class with everyone else around you, asking these questions, and you might even include little tidbits that you might not get just from reading the exam book online.

00:07:56                     

Jason Dinesen: That's exactly right. The in-person is extremely interactive. It's an eight-hour sessions, or thereabouts. It starts at 8:00 or 8:30 in the morning and goes 'til 4:00, and then the exam – whatever. It goes 'til around 4:30 or 5:00, or thereabouts.

Grace Chlosta: Yeah, so give me a little bit of an overview of what that day looks like, because I know you taught at [the] fall [conference]. Like you said, start at 8:00 a.m. Are there breaks in there? What does the sort of flow look like throughout the day?

Jason Dinesen: Yeah. I would say that there are several breaks during the day, and we get lunch. In all seriousness, it's not torture to sit through eight hours on this. It's actually – I didn't think it was that bad, honestly. It really wasn't as tedious as you might think. And actually, in all seriousness, if you think, "You know what? I think that would be really interesting to go to something like that," this is for you.

00:09:07

In Las Vegas, we were joking in the room about how, here we are, trapped in a hotel conference room in Las Vegas. People were like, "Oh, well, there's no place else I'd rather be." And I think they were serious when they said that. 

Grace Chlosta: That's pretty impressive, right. If you're a lifelong learner, that's the place, right?

Jason Dinesen: Exactly. That's right. If the thought of learning about 1099s – these little forms, you wouldn't think they would be that complicated, but they are.

00:09:43

I think that part of CPRS is just demystifying some of these things, and making it less imposing and less scary for you. And again, you know where to turn then to try to find the answers to some of the things that you don't know, but it doesn't scare you anymore like it can when maybe you don't know as much about 1099s and you're kind of coming into it as a newcomer. 

But as far as how the day flows, we start at 8:00 or 8:30, whatever the agenda appoints as our time, and we have a few breaks during the day. We take lunch. And then your exam is from – the last hour, basically, you take the exam. 

Grace Chlosta: So that exam, I feel like I hear from a lot of people that the exam part, taking that in person really scares them. What I will say to you – we always say this on site – [is] it's the most beneficial time to take the exam, when all of that information is fresh in your mind. If you don't pass, that's totally fine; it happens. You get two more chances back at home, within your IOFM account, to take the exam.

00:10:57

But I always say, and I think you would back me up, "The information is fresh in your mind. Just try it." And we do have a high success rate and it's not as scary. Any other tips for the exam that you would say? A lot of people haven't taken an exam or a test or anything since high school or college, right? 

Jason Dinesen: Right. Well, it's an open-book test, so you can use all the resources that you have. Most of the agenda outline of what we cover follows more or less the "Master Guide to 1099 Reporting," and so you have access to that.

Now, obviously, you have an hour to do a test that has 50 questions on it, so you can't look up every single thing, or you won't have time to finish the exam, but you can look things up and take your time. Everything that's on the test is covered during the day, so there really shouldn't be any surprises on the exam. 

00:12:03

I think everybody in Las Vegas passed the test. 

Grace Chlosta: Yes, it's a very, very high success rate, which is awesome. But, again, if you don't pass, I always like to remind people: You do have two more chances to, so you can review everything online. I'm not a great test-taker myself, so I don't know how I would do, so I would probably be excited about the two other options, just as a backup, but it is open-book, which I think does relieve people a lot.

Jason Dinesen: Yes.

Grace Chlosta: I just thought of something, too, as we were chatting, about the importance of certification. So what would you say to someone who's an IOFM member who attends our compliance webinars every month, who listens to these podcasts, reads our articles and updates that we do on 1099 compliance? What kind of sets CPRS apart, would you say, from just attending those member webinars? Why do you think you would want to get certified instead?

00:12:59                     

Jason Dinesen: I think CPRS goes even deeper into things, that's one, so you really learn even more. But the other thing is this is a designation. This is one of those meaningful designations, I think, where you really can become the point person in your organization on this. It's more than just "I went to a webinar on something." The webinars, of course, are quite valuable. I teach multiples ones. They're good to attend. But the CPRS designation shows that you – as I said to the audience – I think I had started saying this and then I went off on a different tangent.

00:13:49

At the beginning, in Las Vegas, I pointed out to people that if you survive this eight-hour course and pass the test, you will be among – I don't even know what the percentage would be, the top one percent of people in the world who know about 1099s. It's probably even less than one percent, if you think about it. 

Grace Chlosta: Totally, yeah.

Jason Dinesen: A fraction of a percent of people who are aware of the 1099 and all of the nuances of it, and that's what this designation does. You become one of the elite, and I don't think that – that's not an exaggeration to say that.

Grace Chlosta: No. It's only going to help your career, too, going forward, if you ever do switch companies or anything. I feel like having this in your back pocket helps you, but also helps you appeal to different groups within your career. So I think you hit the nail on the head there, absolutely. Just the designation and, exactly, [that] you're part of an elite group who know the most you can possibly know about 1099s, so that's super cool.

00:14:58

So more than just certification, we have two other full days jampacked with content at IOFM's spring and our fall event. Tell me a little bit about what the rest of the conference can look like? So, obviously, you do your preconference day. You're teaching a few other sessions. Tell me a little bit about those and some of the other opportunities that folks could look forward to at the event. 

Jason Dinesen: Yeah. Depending on what your interests are, there's all kinds of different things that you can attend throughout the day, on each day, after – day one is the certification courses, but 1099-wise – I believe we're covering the W-9 in a little more depth this year, and we have a few other – I do probably two a day, right? Do you have the agenda in front of you, Grace?

Grace Chlosta: I know. I was just going to pull it up and refresh all of us on what you're teaching. It's crazy.

00:16:02

It's a jampacked schedule. That's what I always like to say. We make sure that you have some fun in there, for sure, with our party, and we like to keep our keynote relatively light. But we have you, obviously, CPRS, first thing in the morning on that preconference day. You're right. The "Form W-9 Compliance, Procedures, and Best Practices. We also have you teaching (which is exciting and we just talked about) "Ask the Expert." So "Ask the Expert" live, some of your top compliance questions that you've asked in 2025 so far – which could be interesting since we've had some really difficult ones. And then, again, "Changes in Form 1099 and 1042-S for 2025." And then "Worker Classification 101: 1099 or W-2?" 

00:16:46

So, yeah, you're busy. And then I think I also just asked you to record a podcast in person, so you're going to be bouncing around from room to room quite a bit. 

Jason Dinesen: There'll be a lot, that's right. Yeah, people can get their fill of 1099, and there's other stuff, too, on accounts payable, accounts receivable, courses on fraud and all sorts of different things, whatever your interests are in the world of… How would you describe it, Grace, vendor management and –

Grace Chlosta: Right. That's what I like to say, too. If you come to preconference day and you take your CPRS certification, I would say you're really good to go there, and then we have so many other sessions throughout the rest of the conference. We have a big leadership track, so if you're looking at not more – I guess a little bit more lighthearted, career growth, how to be a better manager, how to stay positive around negative employees. It's really important stuff to help you feel better and more confident in your career.

00:17:46

Of course, fraud is huge. We have so many fraud sessions at the event with Debra Richardson and Paul Zikmund, among others. We have some great Excel courses as well, and I was going to say, too, if you're listening today and CPRS isn't your thing, but you would like to have a certification under your belt from IOFM, [on] preconference day we also have our AP Manager or Specialist certification. We have AR Manager and Specialist. And if you don't want to be certified, or if you're already certified, we also have a number of workshops going on, on precon day, as well. So again, fraud with Debra Richardson, that's a vendor maintenance and fraud workshop. We have a LinkedIn workshop, again, about enhancing your career; a couple of different Excel workshops; and then Monica Brooks' workshop that she does pretty much every event, which we love, "The 7 Habits of Highly Effective People," which is always really exciting.

00:18:37

Beyond precon day, like we just said, the schedule is jampacked with all of those different buckets of information: Fraud. We have 1099 compliance, leadership. There's just a lot going on. And if you haven't registered yet, there's still plenty of time to do so at IOFM.com. We're gearing up. It's only a couple – not even. We'll be there – well, it'll be over in two months. 

Jason Dinesen: Exactly, yeah. At the time we're recording this, it's not even two months before it starts.

Grace Chlosta: It's crazy, I know. It's exciting, super exciting. So as far as CPRS goes, or anything else about the event, is there anything else you'd like to tell us or any closing thoughts here?

00:19:18                     

Jason Dinesen: I think the only other thing that I would say is that this really is a real designation, a rigorous designation. All of the certificate tracks that you could take are real, rigorous things, and you actually have to – don't you have to re-up, Grace, every two years?

Grace Chlosta: Yeah. Well, you have to maintain your CEUs, so as long as you do that by attending webinars or listening to podcasts, or anything like that, there's ways to maintain your certification. Yeah, it's a rigorous process, but it's so, so rewarding. You'll see if you're there for preconference day and afterwards, as people get their certifications. It's super exciting to say that they passed. We have them all printed for you there. So it's a really, really exciting time.

00:20:11                     

Jason Dinesen: Yeah, I'm looking forward to it.

Grace Chlosta: Yeah, we are, too. We will see you shortly. Thank you all so much for listening today, and we'll see you in just a few weeks, Jason.

[music playing]

Grace Chlosta: Thank you so much for listening to the IOFM podcast. Remember to head on over to the Member Forum to discuss today's episode and provide ideas for our next one. And to stay up to date on IOFM's current events, both in-person and virtually, head on over to IOFM.com.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.