A Smarter Way to Manage Your Bookkeeping: Switching to Accounting Automation

March 23, 2023 Mimi Torrington

Finance VP & CFO setting up bookkeeping automation software

Automation has been a buzzword in the business world for the past decade. But it's still surprising to see how prevalent manual accounting is, with some companies relying on spreadsheets and paper-based systems to manage their finances. If your business is one of them, do not worry – Jason Richelson will walk you through some of the best bookkeeping automation tools and strategies you can implement to improve your accounting & bookkeeping practices.

Jason is the Co-Founder and CEO of Bookkeep, an accounting automation platform for independent bookkeepers, accounting firms, and growing businesses. He is also currently the Owner of Simply Wine and was an EY Entrepreneur Of The Year 2015 Finalist New York Region. Before Bookkeep, Jason was the Founder and Board Member at ShopKeep, Co-Founder of The Greene Grape, and Assistant Trader at Bluefin Trading.

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Welcome back to CFO Weekly, where we're talking with financial leaders about how to build efficiency in their teams, create time for strategy, and ultimately get results. With your host, Megan Weis. Let's jump right in.

Megan - 00:00:18: Today my guest is Jason Richelson. Jason is CEO and co-founder of bookkeep, the smarter accounting automation platform for independent bookkeepers, accounting firms, and growing businesses. More than 850 retailers currently use bookkeep, totaling billions in annualized revenue. Jason, thank you so much for joining me on today's episode of CFO Weekly.

Jason - 00:00:53: Thank you, Megan.

Megan - 00:00:54: Yeah. Today we're going to be learning about you, of course, but we'll also be learning about your accounting automation software bookkeep, which automatically posts daily sales summary financials to accounting platforms such as QuickBooks Online or Zero and reconciles the payment deposits. And I'm really looking forward to our conversation, so let's kick things off with your story and you could share how you've gotten to where you are today.

Jason - 00:01:22: Sure. Oddly enough, accounting was not something that I ever thought I would be part of. That wasn't something that I particularly studied, but I managed to get good grades in accounting. I even studied in Germany. The only class that I passed in German was accounting for some reason. And then my major was finance at NYU. And when I graduated, I actually got recruited to PricewaterhouseCoopers, but not to be an accountant or a CPA or an auditor, to actually work in their software development, which was the computing side, which was sold to IBM. So I actually built accounting systems as part of PricewaterhouseCoopers, and that was my first job out of college. And then I went on to start a payments company, which is, again, accounting. It was in 1999 that blew up. And then I went to work on Wall Street and I did trade desk. I work on a trading desk where I actually did trading, but I also was the trade desk sort of controller. So I reconciled everyone's trades to what they told us we did to the clearing house, and it's basically gone on from there. And then I started my own business. I had a wine store and a grocery store where I did my own accounting. And then that led to the building of a company called ShopKeep, which was a point-of-sale company and again, a point-of-sale system as an accounting system. So it all culminates in what we're doing now at bookkeep.com, which is accounting automation across e-commerce, retail, and restaurant.

Megan - 00:02:54: Yeah. You've had a very diverse and impressive career so far.

Jason - 00:02:58: Thank you. Yeah, without a lot of decision-making, I've just kind of followed what I'm good at and what I like to do, and I'm very lucky that I get to do what I like to do every single day, which is, believe it or not, automating accounting.

Megan - 00:03:12: Yeah, absolutely. And I feel the same for my career, kind of just falling into roles along the way. But have loved every one of them. So as you look back on your career, are there any particular stories or moves that stand out in your mind as turning points?

Jason - 00:03:30: Well, everything that's led into bookkeep has come from my career. One of the biggest problems I had as a retail business owner was finding a bookkeeper who knew what they were doing. I actually was able to find one. She was actually the nanny of our children and was from Eastern Europe, and she was really great. But I trained her exactly on how to do things. She did all the bookkeeping for we had two wine stores and a grocery store at the time. And then when I started a software company and we received VC funding and that was a total whirlwind, but we had a CFO, and we had a CFO office or team, and I was just amazed. I think we had five people on the accounting team. Everything was manual, everything was spreadsheets, and I just couldn't believe that we were a software firm and that everyone was still doing things manually. And it took forever to close the books. And what I realized through a lot of this is where a lot of this comes together. And what we do at bookkeep is on one side you've got most companies don't want to dedicate resources either time, money, or software to the accounting team. A lot of companies feel like they can just hire some more people and you guys will get it done manually with a spreadsheet. And on the flip side, a lot of software vendors and I've been on the other side with Point of Sale. A lot of software vendors like Point of Sale companies and e-commerce companies, they do not know how to. Do accounting. Nor do they care about proper accounting reports, because their job is to help you sell more, sell faster, sell better, not account for it. So what you end up with is where we are at bookkeep is you've got a lot of e-commerce vendors, a lot of software vendors, and point of sale and they don't always build proper summarized reconcilable reports that will match to what's hitting your bank account because that's not their job and they really don't have in house resources to understand that. And on the other side, you have people who have to get the books done who are told you can't use automation, you need to just get spreadsheets or hire someone else. And so we're kind of meeting in the middle there. We're really helping the accounting teams understand the numbers that are coming from sales platforms, reconcile those numbers according to the proper sales days, and then splitting up those batch deposits so they match up to your sales numbers. So basically, daily sales reconciliation. So to answer your question, everything that I've done in my life has led up to what we're doing at bookkeep right now. And I think it's a really interesting space where very few people are focused on because of these dynamics, where accounting teams don't often get automation or get people focused on their automation needs. And sales software companies and payment companies don't focus on the needs of accountants.

Megan - 00:06:16: Yeah, automation has been such a hot topic for at least the last five to ten years and I would think that most of what can be automated has been, but that's just not the case. There are so many companies that are still using Excel and doing things very manually. It always surprises me to find out just how manual accounting still lives.

Jason - 00:06:41: Yeah. And part of it's also that there's just the software engineers and product people. Accounting is always something that if you didn't study accounting or you didn't study business, it's always sort of this black box to you what goes on with the accounting team. Any business owner will say the same thing. Often we don't sell directly to business owners for bookkeep. So, e-commerce vendor, we're not going to go to the owner and say, hey, you should sign up with bookkeep because they're going to say, no, my accountant does that. I don't need this, I don't need this. My accountant does it. Right. The accountants are like, I am completely underwater. This guy just signed up for Woocommerce and he's using Shopify he's got two PayPal accounts and Stripe and I have no clue what's going on but the owner is like, my account handling that right. But what happens is that no one's really focused on this space. No product developers or people who don't understand accounting want to focus on building automation for this space. And so I think that's why it's kind of exciting that this is a place where we really like building software and really focused on reconciliation as automation. And there's really not a lot of tools out there that do that. I mean, there are some at the way enterprise level, but they're generally designed to automate reconciliation within your books. They don't go out and connect to the source systems to get the raw source data to make sure that what you're seeing from the source system is equaling what's in your books. And that's really what we do.

Megan - 00:08:06: I'm just curious, how did you get into grocery and wine? Where did that come from?

Jason - 00:08:11: Well, yeah, that was a long time ago. Well, when I was working on the trading desk and I realized that if you're not a trader, I really was more of the controller for the trading desk. But I did some trading on if you're not a trader working on a trading desk, then you're nothing. So I realized that my life on working on Wall Street wasn't really going to go very far and I decided I always wanted to start a business. I had started a payments company in 1999, and my partner at the time, said, well, why don't we open a wine store in our neighborhood? And I looked and it turned out that wine stores in New York had been banned because of old rules, but they just lifted that ban. And I was like, you know what, this might be a really good idea. So we opened the wine store, and then we opened another wine store in Manhattan and a grocery store. And for me, it wasn't so much about a love of wine or grocery products or anything like that. It literally was, I want to track the numbers. I want to get the books perfect every month. I wanted to see how we're doing. I want to track the profits. So we always had managers who did the managing the team, picking the products and stuff like that. I still own a wine store. My wife runs it in California. She and I put it together and she's running that business in California. So I'm still very close to retail. We use Square in that location so I have access to Square. And we're actually probably the best accounting integration. We are definitely the best accounting integration for Square that's out there. We have customers that have 50-plus locations running Square into one set of books perfectly and everything reconciles every day. I just fell into the wine. But it always comes around to the same thing. It's doing the accounting and now automating the accounting.

Megan - 00:09:55: Yeah, it definitely sounds like bookkeep is the ultimate culmination of your career so far. So maybe you've already done it. But can you tell us a little more about bookkeeping and what inspired you to start this company?

Jason - 00:10:08: Yes, so we actually started as an accounting firm, so we wanted to do just bookkeeping, not tax or audit or any of that stuff. We wanted to get the books done. So we actually started that four or five years ago. We had bookkeepers on staff. We had about 50 clients, restaurants, some e-commerce, and retail. And I wanted to do that because I wanted to go through because the mind of an account or bookkeeper, they're not focused on always improving their process every day. Maybe they want to, and a lot of people do. And we definitely work with some accountants who do have that thought process, but often they're so overwhelmed with, I just have to get these books done. I'm just going to type these numbers in because I got to get it closed by the end of the day. I'm not going to change and focus on anything else. I'm not going to set up new software. I'm just going to type the numbers in to get these books done. So I saw a lot of that. And so what I wanted to do was automate their daily process, make their lives easier, make it automate some of their processes. And so as part of starting to bookkeep as a bookkeeping firm, I had access to a bunch of books to a bunch of clients' data. And I basically cycled through all kinds of different automation opportunities. And what I settled on was what we do now, which is because basically bill pay was available. There are a bunch of tools out there that are available to automate different processes and bookkeeping. But what wasn't really well done was getting the point of sale data from a restaurant to match up to the Grab Hub deposits, to the Uber Eats deposits, to the payment deposits from the terminal, booking all that revenue accurately on a daily basis so that you have accurate daily reporting so that you can do proper comparisons. And no one was really doing that right. Some of the competitors that had popped up in the space over ten years back work backward because they weren't thinking like accountants. So some of our big competitors in e-commerce, look at what was in that deposit. So you get your deposit, and now let's back that deposit into revenue days. And they can only assign that revenue to a single day. So what often happens is your revenue for a four-day weekend hits on a Monday, because that's when that deposit hits. And they might post or backdate that, but it's still not accurate. So we think, like accountants with what we're doing here, we book your revenue the day it happened. It doesn't matter if the money has hit the bank account or not. What matters is you book your proper accrual entry based on what happened that day, and then you reconcile it to the payments. And no one was doing that. That's what we do. And we do it across almost 15 platforms now, point of sale, and e-commerce restaurant Systems. And we're growing that number all the time.

Megan - 00:12:53: So your prime client is a what? small retailer restaurant?

Jason - 00:13:00: No, our customers are accountants. So accounting firms. We just signed a firm that has 350 locations in the pharmacy space. That's an accounting firm. And we're working with them to automate the daily flows from all the point-of-sale systems--s across those locations. We have another accounting firm that I'm not sure exactly how many clients they have a couple of hundred clients. They're mostly working for product brands, so they sell e-commerce mostly. Those are e-commerce clients. But we also work with a lot of awesome, and I would say really sharp, QuickBooks Pro Advisors. When we sign up, QuickBooks Pro Advisors, who might have ten to 30 clients, really understand their stuff, which is great to work with. And they're building their firm, and they want to put automation. And they're really focused on building automation because they know that the automation is what's going to allow them to continue to grow the number of clients they get. And they're a little bit more forward-thinking than some of the larger firms in terms of billing on a monthly basis, which means that they need to get as efficient as possible. So, no, our customers. Now, I should say we do have some very big Shopify stores. We have businesses doing 30 million to about 100 million where we work directly with the CFO, where the CFO has a team in-house and will, you know, the CFO will sign up with bookkeep and we'll get it set up for them and it'll automate for their team. For instance, we have a CFO of a women's clothing brand. They actually have 15 locations, physical brick-and-mortar locations, as well as e-commerce. And our software automates accurate daily postings from each point of sale as well as e-commerce to their accounting platform. And they are using Shopify as their, as their selling platform. So we actually are we can with Shopify, we can handle those types of accurate postings for them. So it's usually the CFO office in those larger firms, but mostly we really focus on accounting firms.

Megan - 00:15:03: And can you discuss some of the key features of bookkeep that are specifically designed for small retailers and e-commerce businesses?

Jason - 00:15:12: Well, if you think about a small business or a small accountant, generally the accountants know what they're doing, but often small businesses don't know how to do accounting properly. So our entries are accurate. If you connect QuickBooks and you connect Square to bookkeep and tell us what day you want to start, we will accurately post accrual entries and match those bank deposits accurately in your QuickBooks. So we do accurate accounting. So if you had to hire someone as a bookkeeper, a lot of bookkeepers aren't always properly trained in how to do those bookings, not to mention the fact that they have to do it manually every day for $40 a month. If you're a small million-dollar business or less, we post these numbers accurately to your books. And so we post daily accrual entries for your sales and then match them to the payment deposits across any different system you're using, whether it's the point of sale or e-commerce platform. But then also one of the things we're announcing this week, we announced yesterday is we just partnered with DAVO by Avalara a division of Avalara. We're taking that same revenue data that has all the sales tax detail. And we're going to allow you to just turn on this feature and send that data to DAVO by Avalara, where DAVO will then take that data. We'll set aside that money from your checking account, and then we'll automatically, at the end of the month, file and pay your sales tax. So that taking that workflow completely off your hands, as well as the risk of filing late. Or I can't tell you, I filed my first sales tax late back in 2003. I actually didn't file it late. It just somehow didn't get postmarked properly. And they charged me, they find me $700. And ever since then, I've been obsessed with making sure sales tax is filed on time. And I've learned as part of being an accounting firm that is a big risk for an accounting firm or even for a CFO office is making sure you file that sales tax on time and accurately. It's a big workflow, it's a big process, and your bookkeeper is sick that week. It doesn't get done right. It's something that is not always top of mind but can really cause problems if you don't do it right every month.

Megan - 00:17:23: So how does bookkeep handle sales tax calculations and reporting for businesses that are operating in multiple states?

Jason - 00:17:31: So what we do is essentially we're a reporting tool. So we collate the numbers. So if you're selling on Shopify, Shopify as an example, Shopify is already properly charging. You have to set up your nexus and everything is Shopify. So you do your settings in Shopify, which is probably already done, but we'll pull that data that Shopify calculated, the jurisdictions, the amounts, the rates, and then we will collate that and send that to DAVO in a format so that you don't have to touch it, you don't have to run spreadsheets. If you ever saw in Shopify, if you've ever seen the report in Shopify for sales tax by state, it's really just a transaction list. It's not a sales tax by state. I mean, if it was rolled up by the state, it would be pretty easy for you to look at those numbers and then go to each state and make your payments. But it doesn't do that. So you still have to do a Pivot table from that data and Shopify, and then you have to go to each state's website and log in and make those payments. So what we do is we send all this data to DAVO. They automatically take those numbers. They actually withdraw the money from your checking out daily, which is a great service, more for smaller businesses who sometimes assume that money belongs to them. And then they will then file and pay that after the month is over.

Megan - 00:18:45: Yeah, that's amazing. I have an Airbnb and it's so nice that that platform does that for me because I wouldn't even know where to start.

Jason - 00:18:58: No, exactly. Marketplaces do that for a lot of customers. But the bigger you get, the you have to start doing it yourself. As we know everyone who listens to the podcast, it's very hard to find staff who know how to do these things. By automating some of these functions that can get you in trouble, I think you can save yourself a lot of pain.

Megan - 00:19:21: Yeah, absolutely. One less thing to worry about. So let's talk about bookkeep and how it integrates with platforms and other tools.

Jason - 00:19:33: Well, we have a direct integration. When you use bookkeep, if, say, you're a Shopify seller, you're going to have Shopify. You're probably also going to be using PayPal. You might use Tesla as after pay you're going to sign up for bookkeep, you're going to connect your Shopify store with an Oauth connection, which if anyone's connected an app to QuickBooks, it's the same pop up window. Are you okay with sharing your data with bookkeep? You're going to do the same thing for Savvy. You're going to do the same thing for PayPal. Once that's done, you're going to also connect your QuickBooks or your Zero. We do also work with Netsuite and Sage intact, so you have to just reach out to us, and we can turn that on for you. Once you make those connections to your accounting platform as well as your sales platforms, you can either allow us to do the mapping because we'll look at how you've been booking before and look for the right accounts, or you can do the mapping yourself. It's pretty simple. But we do have CPAs on staff. Our head of product is a CPA. By the way, I'm not a CPA, but I've been doing accounting software forever. And one of our leads in product and customer care is he was a controller for a restaurant, a five-location restaurant. So our in-house team understands accounting. We're not just app developers. We really understand what accounts have to do every day. So once those are connected, you give us a start date. I want to start for Fed on March 1st with bookkeep and with Shopify. And then we'll start posting those entries every day to your accounting platform so that when you go into QuickBooks, for instance, everything will be a match. When those Shopify deposits hit, when those PayPal deposits hit, when those sales deposits hit, you're going to see match across all of that. And that's what accountants and bookkeepers on a daily basis, they want to see those matches. They don't want to have to then figure out what these deposits are. So then everything will match. And if you just hit the matches on those bank feeds, we can also reconcile the end of the month. But you'll see that your balance and your balance accounts should match. Shopify should match, PayPal should match Tesla, and it really just runs automatically from there.

Megan - 00:21:39: Yeah. That's amazing. Accountants spend so much time reconciling things. This tool must be a game changer for them.

Jason - 00:21:47: It's true. And we're getting better and better at reconciling. One of the things about doing daily sales reconciliation that's so important is that nobody does it, by the way, daily. They should, but our software essentially does it daily for you if you want to make sure that you're getting paid for what you sold. And you think, of course, I've been in retail forever. Yes. When you swipe that card, if you get approval, you're going to get your deposits. That's pretty much 99.9% true. But what happens is, on some of these platforms, Shopify is very good, but there are ways to screw up orders in Shopify, your front end team, if they use draft orders, there are ways that you can create draft orders. They look like in Shopify, those orders are closed and paid for, and they were not paid for. So we've seen holes where draft orders were closed but not batch closed, so they didn't actually get paid for those transactions. And we've also seen issues where other e-commerce platforms don't do calculations right. And we catch those in clearing accounts against what PayPal says. So it can happen. So not only do we book your accurate revenue based on proper accounting, but we also find these problems as long as you're running our system every day.

Megan - 00:23:04: And I'm sure you've touched on this along the way, but can you discuss some common mistakes that small retailers and e-commerce businesses make when it comes to accounting and state sales tax compliance?

Jason - 00:23:16: Well, I think the biggest mistake that small businesses make is not they think that they shouldn't pay very much for an accountant. Unfortunately, you do get what you pay for. You want to hire the right accounting team, whether it's a QuickBooks Pro Advisor or if it's a bookkeeper in general. Bookkeepers. Sometimes small business owners assume that their bookkeeper is an accountant and it's going to book everything accurately. But most people who probably listen to this podcast, if they're an accountant and they see lots of books, every time they see a new set of books, they see they have a mess on their hands to clean up. So what happens is a lot of small businesses, they just don't think that accounting is important. But Warren Buffett says accounting is the language of business. And as a business owner, you do need to understand your accounting. You do need to close your books every month. You need to know how you're doing. You need to understand what those numbers mean on the balance sheet on the PnL. And so you need to hire someone who knows what they're doing. And it's not going to be $15 an hour anymore, unfortunately, but it's really worth the money. So that's the biggest mistake that they make is just not hiring the right accountant. But again, every small business owner will tell you it's so hard to find one, the really good one. We have a lot of partners at bookkeep. They won't take new clients right now. They just can't do it. They don't have the bandwidth to handle new clients. So it's a really tough thing. But you do need to focus on closing your books every month and making sure that your accountant is doing it accurately. And yes, as a small business owner, that means you need to learn accounting which is your own business. And accounting is the language of business.

Megan - 00:24:56: Yeah, too often it is an afterthought. And really, accounting is the heartbeat of any organization. So do you have any favorite success stories as you look across the clients that you serve?

Jason - 00:25:12: In terms of what we've done?

Megan - 00:25:13: Yeah.

Jason - 00:25:14: We learn a lot from our clients. There's really no way around it. So we end up getting I would say, actually, yeah, we have one client in the early days of bookkeep. So like a year and a half ago, I had a special where I allowed some QuickBooks Pro Advisors to sign up and get unlimited clients. They could have as many customers as they wanted for $99. That was a limited-time offer. One of those QuickBooks Pro Advisors, she's picking up a lot of customers, and they're really complex e-commerce customers with multiple PayPal accounts and multiple stripe accounts. Maybe they have two or three Shopify stores as well, all dumping into the same QuickBooks. Right. And she had no idea how any of this worked. She managed to find us, and she's been very helpful to us. I think we've been very helpful to her. She's really learned how these data flows work. And we've found issues with Woocommerce and all kinds of different platforms because she's working with so many different platforms. So that's actually turned out to be a really big success. I've been working with her actually this week in reconciling some of these accounts. And I guess a back and forth. I mean, a lot of people think an app is just, you guys are software developers, you build apps and they're just going to be perfect. But when you're in the accounting space, everyone's still trying to figure things out. And so we see a lot more than your own accounting team is going to see. Your own accounting team might know how Shopify works and PayPal works. We know how Shopify and PayPal work, and we've also seen so many different implementations and errors, and problems. But we've also seen Woocommerce, we've also seen big commerce. We're connected to all the platforms and all the different payment providers. I know that Grab Hub deposits every Wednesday of the month and Grab Hub deposits also on the last day of the month. We understand the full deposit timelines of all these different payment providers as well. So my point here is that our success is when our clients are open to working back and forth with us. And we do, we'll set up slack rooms with your team so that we can have back-and-forth communication. And the way we think about ourselves is not so much an app as we're your back office team for revenue accounting. So our software does most of the work, but if you have a question or you have a new app to connect or you're not sure, do you work with Tesla or do you work with after pay? You can slack us in our slack room or of course chat with us through the app because we do on our staff have team members who are accountants. We understand how this works. We can look at your books and see if something was mapped incorrectly or help you reconcile. So I think the big success for us is really when we work closely with an accounting firm that's willing to trust us. And then we can grow, And then they can grow.

Megan - 00:28:06: Yeah, a lot of value that you guys must add there.

Jason - 00:28:09: And we love this stuff.

Megan - 00:28:11: And what are some of the biggest challenges that small retailers and e-commerce businesses are facing at the moment?

Jason - 00:28:18: Well, they're going to tell you it's going to be getting sales and a lot on the sales side and there's a lot of tools out there to help them with that. I would say also one of the biggest problems is refunds. Refunds now, especially now the economy has changed, there's been a lot more work done in refund processing and basically, there's been a lot more refunds and returns for e-commerce. And there are a bunch of tools out there that are helping automate that process of returning products to e-commerce vendors. But as we're learning, a lot of those tools are not doing the accounting right. And sometimes post entries to QuickBooks, sorry, not to QuickBooks, but to Shopify that we have to handle. And it's the same thing. It's an app developer who is looking to solve a problem for an e-commerce vendor but they don't know how to do the accounting for it and that's not a focus of theirs. So we're one of those things that it hurts the business, of course, when you have to do a lot of refunds and that's hurting their business. But actually accounting for those refunds properly is one thing that we've been seeing recently, and is something that we have to get better at and help out.

Megan - 00:29:29: And if our listeners remember just one piece of advice today, what would you want it to be?

Jason - 00:29:37: Well, I think that you should think of app automation as it's a tool for you. I don't think QuickBooks is not a tool. QuickBooks is a piece of software. It doesn't automate. You have to go in and do things right. But proper automation software is going to do those things for you in QuickBooks and it's not something you should be afraid of. I know if there are CFOs and accountants are on listening to this call, they're not worried about automation because they know the work has to get done. Everyone listening to this podcast knows the work has to get done. And I either have to find someone and train them to do it or give them access to all the tools so that they can get the data so that they can do it. Or I need to find an automation tool that I can show them how to use that helps them and then they can manage the automation tool. So you're not necessarily giving the automation tool to work, it's just a change in workflow. So your team is now managing automation tools and then managing the connections and working with the clients to get the access to the data they need so that the automation tools run and their time isn't spent creating a journal entry, creating a sales receipt, typing the numbers in copy and pasting out of spreadsheets. So I think don't be afraid of automation. Software is the thing. And I do think over time, as we all know, it's very hard to find team members to do this work. Automation is going to be the big solution for this. I need more people more app developers to be more open to working with automation tools. My biggest problem is I cannot get data out of Grab Hub directly. I cannot get data out of Uber Eats. Half the point-of-sale systems we work with do not have APIs. So we have to take data files that the customer still has to download and send to us because there's no automation. And that's one of the biggest problems that we run into is that these vendors don't care about the accounting side, so they don't build automation or automated access to data. And that's really where people listening to this podcast, if you're a big user of Uber Eats or Grab Hub or you have 100 location installations of some point of sale system, you really need to be hard on your vendors to make that data available through APIs or automated emails are fine as well. Or believe it or not, FTP would be fine as well. So that we can than daily process that data without a human having to be getting involved. The humans are always going to need to be there because they need to make the connections they need to set it up, but then the automation can run from there.

Megan - 00:32:23: So lastly, as a finance leader and an entrepreneur, what keeps you motivated? What excites you about what you do?

Jason - 00:32:33: What excites me still? I mean, what I get drawn back to is I am obsessed with the automatic reconciliation of accounts. I know it sounds silly, but I personally work on building our internal tools to automate reconciling or at least find errors in accounts so that you don't have to. That's what I like to do. Unfortunately, I can't do that all day, so I still have to continue to build the business and hire and train and market what we're doing. But I think it's important that someone from outside the accounting industry is I'm not a CPA, I'm not an accountant by training. I'm definitely a software entrepreneur. But I love accounting and I think that's what it takes to get proper automation tools in place because sometimes accountants are so overwhelmed and so underwater and so overworked that they really can't pick their heads up to even think about some of these things. I'm motivated to solve that problem, which is helping accountants and CFOs automate and get their numbers done monthly. I really do think that as a business you need monthly numbers and it shouldn't take a team of five and a bunch of spreadsheets and pivot tables to get those numbers done every month. And of course, it takes weeks and weeks when they do it that way so that's kind of what motivates me.

Megan - 00:33:55: Yeah. Well, it definitely sounds like you're doing just that.

Jason - 00:33:59: We are. Every day, all day long.

Megan - 00:34:02: Jason, thank you so much for being my guest today.

Jason - 00:34:05: It was great to be here. I think this is a super exciting space. It's changing over time. And as we see in the accounting space, there are a lot of companies that are starting to automate accounting and so accounts need to also use automation tools to compete with that. As more firms are starting up to do that and more investment dollars are coming into the accounting space because it's a very fragmented space still. And so it's a huge opportunity and it's a lot of fun.

Megan - 00:34:38: Yeah, and you're right. I mean, it's the only way accounting firms and accountants themselves are going to get ahead is to automate a lot of the stuff that can be automated.

Jason - 00:34:47: Absolutely.

Megan - 00:34:48: Well, I've really enjoyed speaking with you and I appreciate you taking the time to be here with me today. And I wish you and bookkeep all the best. Sounds like you're both doing really great things. And to all of our listeners, please tune in next week. And until then, take care.

If you're ready to boost efficiency and streamline your accounting processes at significant cost savings, it's time to talk with Personiv. Their people-powered solutions have transformed the delivery of back office tasks and general accounting functions for decades, partnering with clients to provide everything from accounts payable to payroll services. See what Personiv can do for you by visiting personiv.com.

You've been listening to CFO weekly presented by Personiv. Please subscribe wherever you get your podcast to hear all of our episodes. Want to learn more? Check out personiv.com. Thanks for listening.

In this episode, we discuss:

  • How does Bookkeep help businesses automate their accounting function?

  • Revolutionizing the accounting industry

  • The benefits of automation for small business owners

  • How does Bookkeep handle sales tax calculations and reporting for businesses operating in multiple states?

  • Overcoming accounting and sales tax compliance mistakes

Key Takeaways

Bookkeeping Automation

Quote bookkeeping automation

Finding a good bookkeeper who knows what they are doing, combined with the difficulties of manual accounting, led Jason to found Bookkeep, which helps companies automate their accounting processes without having to dedicate resources or hire more people.

“We're really helping the accounting teams understand the numbers coming from sales platforms, reconcile those numbers according to the proper sales days, and then splitting up those batch deposits so they match up to your sales numbers,” Richelson said. - 03:22 - 06:16

Integrating Point of Sale Systems with Bookkeeping

Quote point of sale systems with bookkeeping

Bookkeep was founded with the vision of revolutionizing the accounting industry by simplifying and automating the tedious daily processes that bog down accountants. While there are many similar tools available, Bookkeep stands out for its ability to accurately book revenue on a daily basis. This ensures that daily reporting is precise, timely, and reliable. Bookkeep understands that it's crucial to book the proper accrual entry based on what happened that day, which is why their system is designed to capture all relevant data and translate it into actionable insights.

“I wanted to automate accountants' daily processes and make their lives easier,” Richelson said. - 10:00 - 15:04

The Benefits of Bookkeeping Automation for Small Business Owners

Quote Jason Richelson, Co-Founder and CEO of Bookkeep

Often, small businesses don't know how to do accounting and bookings, not to mention they have to do it manually every day. Bookkeep does accurate accounting, posts daily accrual entries for your sales, and then matches the payment deposits across any different system you're using, whether the point of sale or e-commerce platform. The company also announced the partnership with DAVO by Avalara, a technology company dedicated to automating sales tax.

“I've learned, as part of an accounting firm, that a big risk for an accounting firm, or even for a CFO office, is making sure you file that sales tax on time and accurately,” Richelson said. - 15:04 - 17:23

Integrating with Bookkeep

Quote integrating bookkeeping with automation

Bookkeep integrates with other tools such as Shopify, PayPal, Sezzle, Afterpay, QuickBooks, NetSuite, Sage Intact, and more to help automate financial functions such as posting entries daily to the user's accounting platform and reconciling payments across all systems used.

“We're getting better and better at reconciling...our software essentially does it daily for you. You want to make sure you're getting paid for what you sold,” Richelson said. - 19:25 - 23:04

Overcoming Accounting and Sales Tax Compliance Mistakes

Quote overcoming accounting compliance mistakes

Small businesses think that they shouldn't pay very much for an accountant. But you do get what you pay for. Some also assume their bookkeepers are accountants who know how to make everything work well. As a business owner, hire someone who knows what they're doing, start learning and understanding your accounting, close your books monthly, and ensure your accountant does it accurately.

“A lot of small businesses don't think that accounting is important. But Warren Buffett says accounting is the language of business. And as a business owner, you do need to understand your accounting,” Richelson said. - 23:04 - 24:56

For more interviews from the CFO Weekly podcast, check us out on Apple Podcasts, Spotify, and our RSS or your favorite podcast player!

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Learn how you can incorporate automation into your bookkeeping efforts. Get in touch with the Personiv team to find a perfect plan to achieve your goals today.

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