Do you like dealing with people or properties? Most real estate investors and property managers leave dealing with numbers to their accountants.

Today, I am talking to Kyle Redding, Head of Growth and Sales for Proper. The property management tool uses artificial intelligence (AI) and machine learning (ML) to provide accounting and bookkeeping services. As a former CPA, Kyle has extensive knowledge of accounting, bookkeeping, and customer experience.

You’ll Learn…

[05:12] Purpose of Proper: Partner with property management companies to set up accounting automation for back office.

[06:10] Proper Position: Works with, doesn’t replace other property management tools.

[10:00] Sophistication Fog: Property managers who need additional software and staff to optimize accounting automation.

[12:15] Proper Process: Property managers handle invoices via dedicated email inbox, training, and automated processing.

[17:45] Reminders: Rent is due! Rent is late! Proper’s frequency of property management invoices and statements.

[21:10] Proper Competition: Hire bookkeepers/accountants with qualifications, education, and experience to alleviate single point-of-failure.

[29:55] Proper Pricing: Affordable and sliding-fee scale based on price per unit.



Kyle Redding’s Email


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DGS 101: Take Confusion Out of Property Management with the Proper App 

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Jason: Welcome, DoorGrow Hackers, to the DoorGrow Show. If you are a property management entrepreneur that wants to add doors, make a difference, increase revenue, help others, impact lives, and you are interested in growing your business and life, and you are open to doing things a bit differently, then you are a DoorGrow Hacker.

DoorGrow Hackers love the opportunities, daily variety, unique challenges, and freedom that property management brings. Many in real estate think you’re crazy for doing it, you think they’re crazy for not because you realize that property management is the ultimate high-trust gateway to real estate deals, relationships, and residual income.

At DoorGrow, we are on a mission to transform property management businesses and their owners. We want to transform the industry, eliminate the BS, build awareness, change perception, expand the market, and help the best property management entrepreneurs win. I’m your host, property management growth expert, Jason Hull, the founder and CEO of DoorGrow. Now, let’s get into the show.

Today’s guest is Kyle Redding of Proper. We’re going to be learning about what Proper is now. I think we’ve had you guys on the show before and it’s different. Kyle, welcome to the Door Grow Show, glad to have you. Let’s get into your background and maybe you could share with people your entrepreneurial journey, I think you have a cool story and I think it’d be fun to get into first.

Kyle: Yeah, thanks, Jason. This is exciting, thanks for having us. Up at baseball in college really all I wanted to do fell into accounting. That sounds a little crazy, but Accounting 101 was in all those classes that I took and got 100% in. Don’t ask me how, but it just happened. While playing baseball I was like, “Okay, I think I can do this.” You travel a bit, you miss a bunch of classes but still, somehow worked it out.

That revolved into an internship with Ernst & Young and then ultimately, a full-time job. I started up at EY in Orange County, California for about five years or so in the real estate group. A lot of my clients were public REITs or real estate developers. I ultimately then transferred out to Australia where I work at EY. Again with some real estate clients and some other industries.

Ultimately, I got out of the public accounting game and was attracted to start-up life. I found this little start-up in Australia that was looking for an accountant that could sell, and I thought I’d give this a crack. We are a little finance online payment company in the professional services, all of our clients were accounting firms and law firms. We got really deep into the accounting industry and the CPA world and how they run their business.

We grew that business and brought it to the US about four years ago. I took that company public in July last year. While that happened, I’ve always stayed in touch with one of my best friends, Matt, who is our COO and head of finance at Proper and Mark, an old college roommate from USC. We used to make surfboards and Matt and I worked at Ernst & Young together.

At that time, Proper was really trying to solve a lot of different challenges for a property managing company, mainly on the maintenance side, which I think he comes and talks about before. Mark, our COO, was just religious about user research and first principles, light up thinking, breaking down problems, and finding the best solution for those problems; which is how we ended up coming back to Matt and I’s core background from the CPA world and real estate and addressing that […] maintenance side of things, which is a nice to have and people want that to be better.

The real true problem that we found was on the accounting side. A lot of property managers don’t necessarily get into this business because they like doing the accounting, or they do not do the accounting because (like you said) different from the real estate sales. It allows them to grab a hold of these owners and these properties, and develop other business opportunities but at the end of the month, the key deliverable that they all have is a financial package on that owner’s investment. That’s where we are today, helping a lot of property management companies solve that challenge and get better and focus on growth as opposed to running a call center and operations.

Jason: Cool, so let’s get into how would you describe Proper now to those that are listening? What does Proper do?

Kyle: Yep, sure. We partner with company management companies to help automate their back-office essentially, from everything, from AR to AP, to bank […], to owner reporting. We use very high caliber accountants who have all got an accounting degree from big universities, that work in a big board accounting firm, that works at a Fortune 500 accounting firm. We power our team with machine learning, automation, and artificial intelligence to help make their job easier and allow our clients, the property managers, to scale a lot faster without having to worry about hiring more staff for training those people or maybe delaying, bringing on more portfolio because they need to do those things before they can get to that next step. We focus on accounting automation.

Jason: Help me understand then how that works. Most property management entrepreneurs and business owners that are listening to the show right now are probably thinking, “Well, I’ve already got AppFolio, I’ve already got Rent Manager, I’ve already got Buildium. I’ve got a property management back office or accounting solution.” Is Proper something that you guys are positioning yourself to replace these tools or is this something where work in conjunction? How does this work?

Kyle: Good question. We work alongside all of those tools. We’ve got a big mix, we don’t just work in AppFolio, we don’t just work in Propertyware. We’ve got clients that use Buildium, use Yardi, AppFolio, Propertyware, Rent Manager, you name it. We’ve even got clients who start out with QuickBooks and then as we help them grow, we transition into something more appropriate like a property management software.

Right now, we’re not looking to replace any of those tools. We help optimize them for our clients. We help them set up a foundation to better utilize those and then manage those as well. A big part of what we do is helping them set up the appropriate level of internal controls. Are they set up for growth? Is that foundation there to really pile on top of?

When we take on a new client, a lot of times it’s retooling the way they’ve set up AppFolio, Buildium, or Propertyware. It’s helping them get their […] matrices set up. It’s all of those things to create efficiency, get them out of the weeds of the mundane repetitive low-level tasks that are […] time set from their day, put that on to our plate, and get them back out to the field, so they can grow their business.

Jason: It’s not just accounting because you’re helping with some of the operational aspects as well.

Kyle: Correct. What we found is depending on a property manager and the company and the way they’re staffed, there’s a lot of leaving in and out of that accounting process. There’s a property manager who might spend 10%–15% of their day doing some accounting function that they probably shouldn’t be doing. The other side of that is you might be the owner or the broker-owner going, “I wish my PMs are out there losing these vacant apartments I’ve got, but they’re stuck doing this paperwork because there’s no one else to do it,” or it’s part of a process that they set up that hasn’t been revisited or fine-tuned. So, we help alleviate all those little bits of pieces there, then create more capacity for them to focus on what they want to focus on.

Jason: Is this difficult to get going, get set up, and is there a certain level that a property management business owner has to be at before it would make sense to work with you guys?

Kyle: Let me tackle that second question first which is do we have a minimum or a certain size. The short answer is no. We’ve got clients who have as little as six units. We’ve got clients who start with us at say 30 units and grow to 50–60 within three months. I’d probably say where it starts to make the most sense where they can move away from that one part-time admin or office staff handling some of these admin related tasks or accounting related tasks. Generally, to make it to that 30–40 unit mark and they’re starting to gain some momentum and get a little serious is where we can usually help them get to that next level.

Where we see a clear difference is with somebody’s property managers who we call in the sophistication fog. They’ve half thought on their AppFolio or Yardi to do some things for them, but they still have some low-level staff that may or may not have an accounting background. They’re essentially taking off things on the checklist on a daily basis to help get that job done but there really isn’t an optimization to that process yet, it hasn’t really been optimized. We can come in and create efficiencies for them and help them, ultimately, have them repurpose those people to maybe a more interesting role or a more revenue-generating role, and then start to use some automation and fine-tune their property management software to do more for them.

Jason: When it comes to automation and the technology side, do you guys have a homegrown software that’s running and doing the stuff? Are you using a certain software platform that you work within?

Kyle: We continue to optimize and build other tools mainly around AP. Our goal is to attack one of these functions at a time. We found by measuring our accountants’ time that on average it takes about 5 minutes and 59 seconds to process an invoice. We built a proprietary tool that allows us to take that 5 minutes and 59 seconds down to (say) 30 seconds. From a scaling perspective, that property manager then takes on another 200 units. There isn’t the fear of being able to handle that, and we don’t need to staff another five people on their account to get that work done. We can continue getting through that work at a very high accuracy rate by training our model over and over with the different touches and windows that we see.

Jason: How are the property managers feeding stuff into the system as if they’re feeding it into Proper?

Kyle: Just like maybe a more specific property manager we may have set up where, let’s say 70%–80% of their invoices from their […] vendors are coming in by email. They might have a dedicated inbox, or If they don’t already have something like that set-up, then we’ll help create something like that. We’ll work with their vendors and their team to start training those invoices to come through to that inbox, at which point we can then adjust them and start processing them through our automation tools.

Jason: What are some of the big questions that you’ve been getting? Everybody’s using their property management software, they probably have their systems and processes going to where they’re afraid to even mess with it a little bit, they feel comfortable. Then hearing you say, “Hey, we can help you make things faster. We can make it better, we can help you utilize things better, we work alongside,” and they’re probably thinking, “This is going to be really expensive, I don’t know if this makes sense. I’m going to have to do something different or something new.” What are some of the concerns and how are you addressing those? Maybe you can address them here so people listening, they’re popping up in their head.

Kyle: Sure. I’ll probably revisit one of the questions you asked earlier which I didn’t address, which was what does it look like to get started or to start working with us? What does that process […]? Our onboarding process, usually depending on the size of the PM, say, between two and four weeks to where we’ve fully taken over the accounting work off of their plate.

When we start working with a new client we’ll basically do a deep dive walkthrough through every single one of their processes that they have. We’ll then document that process, so if they do continue to grow or they want these policies, procedures, and manuals for their own internal use, they’ll have those and we can use those to hire additional staff as they continue to grow.

That’s probably a big first step, is understanding what they do, how they do it, what is being done, who’s doing what, et cetera. During that onboarding process, if we see a glaring opportunity for an improvement or an optimization, we’ll help them execute it right there on the spot. In the first instance, we’re going to match what they do so there’s the least amount of distraction to their day. Then over time, the next 30-60 days, we’ll tweak that some more and optimize it a little bit further to where they’ve got a smooth running engine behind […] essentially.

That’s a big question for a lot of prospects of clients that we take on is how do we get started, how does this work? That’s a very high level.

Jason: Let me recap that. Some of these direct out with accounting, they’re frustrated with some of their internal processes connected to these, their day-to-day, and in 2–4 weeks you feel like Proper can significantly lighten their load and allow them to breathe.

Kyle: Yeah. For example, just in the last month, 80% of our clients had increased their unit count on a month-to-month basis. Obviously, there are ebbs and flows, they might lose an owner (which drops the units), but generally speaking, once Proper gets in there, we alleviate and free up. We have one client, we freed up 35 hours a month of their time. This is a seasoned property manager who’s just, at the end of the day having to review work, or they were using another accounting partner.

Jason: Then roughly how many doors did they have that they were freeing up that much time?

Kyle: About 200, let’s say. Not a massive one but a decent-sized property managing company. Working with Proper, we generally saved in terms of card cost of headcount, up to 30% of their accounting staff wages over time. Maybe not on day one because if we’re not going to replace a team, that comes in phases, but over time, we generally see about a 30% cost reduction. We can fix this cost for them as opposed to them running a call center. They want to be making more money so let us fix this cost for you. Keep the quality at a very high level so that financial output and what you’re delivering to your owners.

We also see a significant reduction in the number of questions or queries that our clients get from owners every single month because now our accountants are coming in and doing things may be the way they should’ve been done before or at a slightly better cadence or faster cadence which helps them keep their relationships.

Jason: What are you seeing in all the property management businesses that you’re working with? How often are they sending out statements? Rent is sometimes trickling in. Rent […] coming […] a month. Sometimes it’s late, rent is really late. In these situations, what are you seeing as a frequency for invoices going out?

Kyle: Definitely ranges depending on who it is that we’re taking on board but ultimately during that onboarding and stabilization period, generally it’s within 60 days or so. We have them all recording on the 10th of the following month and that’s a pretty standard cadence across the industry, but we make sure it’s consistent. There isn’t that, “We’d like to get it done by the 10th. Sometimes it’s the 15th or sometimes it’s the 20th.” We try and help standardize that across all of their owners. That might even come down to giving them some advice around, “Hey, you don’t have this clause in your owner agreement negotiated property, let’s help you fix that real quick.” That way you have some consistency. There are fewer exemptions and less, “Oh, this one requires that and this one requires that.” Again, building for scale, they can make those tweaks and continue to pile on top of what they’ve already built.

Jason: One of the questions that pop up in my head hearing about this and owners giving some of their subs, they’re concerned about checks and balances. How am I going to make sure everything between my management software reconciles with my trust accounts, banking accounts, and everything is going in and out? How do I make sure everything is legit and stable? If I’m going to hand it off to somebody, I want to feel safe that these checks and balances are in place otherwise I’m going to have to check everything. Isn’t that true?

Kyle: Yeah. A big way that we approach that is through those onboarding walkthroughs. When we do a deep dive into each process, whether it’s collecting rent or AP, or with the owner recording if there are only […] there, we go into extreme detail, we document and create a manual for that process. Then there is a consistent agreed way of doing it, whether we try to make recommendations to improve it, or we say, “Hey, you guys have got some great process here.” We just formalize it in that way there’s a clear line of, “This is how it’s going to work.”

Then we use tools to keep people accountable. Set reminders for (say) someone on the PM side, they haven’t approved an invoice for us yet, we need to garnish their approval. We use tools that allow us to keep those people accountable, so we can keep them […].

Jason: Short callers and text messages?

Kyle: We communicate daily pretty much with all of our clients from Google Hangouts, workflow collaboration tools, things like that, so there’s clear visibility.

Jason: What are some of the other frequently asked questions that people give you when they’re going through the sales prospects sort of process with you?

Kyle: What are our qualifications, what makes us qualified to do this sort of thing. As I said, Matt and I—Matt is our head of operations—we’re both CPAs with extensive real estate experience at Ernst & Young. All of our accounting team—I think I mentioned this before—got an accounting degree from college, they’ve worked at a Fortune 500 company, or […] accounting firms. Our staff is not your run-of-the-mill bookkeepers. They’re highly trained, they’ve got extensive experience, we require our team to do at least 10 hours of CP in real estate accounting every year, that generally gives them some confidence.

Then we’ve got some clients out of their really sticky situation with back books and unreconciled accounts for a long period of time and if we can come in and clean that up in a very short amount of time. We have one client who had nine months of unreconciled accounts, and we helped clean that up in about 3½ weeks. When we can show our clients that we can do this for them and help them get to a part where they can sell all their managing company and their portfolio, that speaks volumes for the rest of the people that we talk to.

Jason: Let’s throw stones at some of the competition.

Kyle: Sure.

Jason: One of the main competitors is going to be the property management that’s like, “I’m just going to go higher because the alternative will be I’m going to go higher than somebody. She’ll help me with my bookkeeping or my accounting, or data entry with checks and invoices and all this kind of stuff.” They bring in somebody, they’re probably one of the lowest-paying members of their team, and they’re trying to teach them how they do it and it gets really messy. I don’t know if you want to say anything else, maybe I already threw stones at it.

Kyle: No, that’s good. It’s definitely a challenge that we come across, where they’re weighing up, “Do we do this in-house or do we bring on a partner like you guys?” What we often see or hear from people who maybe have gone down that road and then maybe come back to someone like Proper is that it’s a single point of failure. It’s one person who’s a real accountant. They go on vacation, things get missed or they get tired if they’re growing quickly, and they’re not organized. All of those things are risks that a team like Proper doesn’t let happen because we have more than one person while working on your portfolio. We could do that and your pricing is still fixed. That’s one of the ways that we help alleviate those sorts of risks from that setup but that might be the right set up for some people.

Jason: Yeah, I’m sure every property manager that’s brought anybody else in to touch anything financial in their business has noticed some really ugly mistakes that they’re having to clean up. They’re having to reissue their statements, they’re having to undo or apologize for a notice to quit or something that went out to the tenant that shouldn’t have.

Let’s compare this now to just going and getting an accountant, like somebody maybe, “I’m going to go hire a local accountant. They know my area, they’ll get to know my business. Steve down the street, this guy, CPA.” Let’s throw stones at that now.

Kyle: The biggest downside to that scenario is that they’re often doing things in arrears. The accountant isn’t there, the CPA isn’t there every day to do and process invoices or reconcile the bank account. They usually come in the first week of the next month to catch up on everything. The client isn’t super organized, they’re going to have to be digging through things, distracting their clients, asking them questions about stuff that happened three or four weeks ago. Which can be a big challenge. You might be able to navigate through that and create some processes, but that can be burdensome. Even more at a time sucks especially if people on the go are not doing things the way they should be along the way.

With our team, we’re reconciling bank accounts on a daily basis as transactions go through. We’re processing invoices instantaneously as they come through. There are benefits of us essentially being an extension of your team, just maybe not sitting in your office, but having the same people every day in and out doing that work for you as you go.

The other thing about the traditional CPA firm is they’d rather do the higher margin advisory work, tax consulting. It’s expensive for them to do the low-level bookkeeping. They’ll do it for a relationship, but they don’t necessarily like doing it. We actually get a lot of referrals from CPA firms who have clients who need property accounting done at an affordable price.

Jason: You go get an accountant, they’re looking at things after the fact, they’re pointing out things you need to clean up, they’re disrupting your day. You’re having to communicate with them, you’re trying to find the problem they’re pointing out rather than these things being taken care of on a day-to-day basis. If you guys fix something that’s messed up within a day or even two, it’s dealt with. Thirty days later, some stuff to undo your mess.

Kyle: Correct.

Jason: What are some other alternatives to going without Proper? I guess doing it themselves.

Kyle: Yeah, doing it themselves but again you’re constantly fighting that growth battle. How do I get to the next stage, whether it’s right? We all look for leverage to put us into that next zone. We get a lot of clients coming to us who want to grow. They get to the point of, “I can’t do anymore. I need a partner to get to the next stage.”

We get people who’ve been burned by other accounting partners who maybe just don’t have the same quality control so now they’re looking for a new partner that isn’t going to mess things up that they don’t have to keep an eye on.

I think because we focus exclusively on property managing companies, we’re not doing restaurants, we’re not doing eCommerce businesses. We’re 100% real estate accounting. That gives a bit of confidence in partnering with someone like us.

Jason: Got it. If you’re working with some sort of accounting bookkeeping firm, you’re having to force the system, and you’re having to explain to them what you do and that rent’s going to come in, and certain amounts are going to be taken out, and all of those kinds of mess, and they just don’t get it. You’re having to use every time, like change the account rep that’s working with you this company has turned over. That can be a mess, you can guess it.

Any other frequently asked questions that people come in to look at your firm would maybe want to hear on this podcast?

Kyle: How quickly we can get started with people or whether we can help them retool their software stack. Another one we get quite a bit and gotten quite a bit recently is “Can you handle our overflow accounting?” As in they might already have a full accounting team with that capacity that they’re hungry to grow, and they want to buy four portfolios in the next quarter 400–500 units each. “Can we engage you guys to help do the mapping and the chart of accounts to our chart of accounts and the monthly accounting into a ready to transition them from whatever software they are on now to ours?”

We handle a bit of our work as well or even maybe some ad hoc research of which one would outgrow this solution, what else should we look to do. We can scope in that sort of work and continue to partner with them on their growth.

Jason: Okay, pricing. If we can really give any numbers here but if you can help people understand how do you price this out, how affordable this is, how does this work?

Kyle: Great question. Our pricing scale is part of our client’s scale. As in the price per unit drops, the number of units continues to rise. We might start out someone with $12.99 per unit, we might have 100 units. Then if they get up to 2000 plus, we could get as low as $6.99 per unit. We calculate on a monthly basis and as the unit count fluctuates we adjust the pricing, so it’s a fixed note cost for them each month based on their unit count. If we don’t have to work on 100 units that they lost last month then cool, their fees are going to reflect that. So, between $12.99 a unit and $6.99 per unit per month for a full suite service.

Jason: Got it. Well no matter how you work the numbers, doing that here at my screen, it’s going to be a lot cheaper than even a part-time employee generally would be. That’s handling the stuff, that’s a single weak link in the chain, that can be a bottleneck, that might get sick, go on vacation, or whatever, or yourself holding the entire company back because maybe this is not your area of genius or your life’s purpose to handle all this stuff.

Kyle: Yup, exactly. We don’t necessarily provide à la carte services or our different functions of the accounting process other than accounts payable. We know that AP typically takes up about 60% of the time across the entire accounting function. We can get scale on AP pretty quickly especially with automation.

If we’ve got someone who’s looking to maybe test us out, try before they buy sort of thing, we might take on just AP for them or maybe 60% of their workload at an appropriate price point for them to handle just AP, then move that into taking on the rest of their accounting services. Otherwise, we get people who just say, “We need this, let’s get started right now.” We’ll work with their team, get up to speed in a very short period of time, and then take everything off their plate.

Jason: It’s just crazy to imagine that some of the property managers are going to listen to this. You’re dealing with some of the stuff, you’re running into headaches, you’re frustrated, this could be dealt with based on what Kyle’s saying here in like a month. It could be literally off your plate and your life could be infinitely easier.

Kyle: That’s very true. We do start taking stuff off their plate in the first week or two but that first 2–4 weeks we like to really just make sure we’ve got a good understanding of what’s going on so that mistakes don’t happen, so that by week 4, we’re fully optimizing, we’re ready to roll.

Jason: Cool. Well, I’ve gotten too deep with you and some of the members of your team and I know you guys are sharp. This sounds even better than what I thought we were going to be talking about today, so it sounds pretty exciting. I’m sure you’ll get some people reaching out that are running into some difficulties […] off the top of my head that has been complaining about some of the stuff so it should be interesting to see the attraction you get on this episode.

Kyle: The main thing, Jason, that we wanted to do is really give our clients their time back and give them the confidence and reliance on this financial that every month they got to deliver to their owners without having to worry, want it to be consistent, and want it to be high quality. We want them to not have to fear about getting right or spending time checking things. We want to be their partner in growth. We look for clients who want to grow and are like-minded with us to really help transform their business.

Jason: I think those types of clients are my type of clients. These are the people that are focused on growth, so awesome. This is the Door Grow Show so hopefully, the people listening are that type of people. How do people get in touch with Proper? How do they get started? What’s the next step for those who might be listening that might be interested?

Kyle: My email is You can check out our site Shoot us a note. We’d love to do a free consultation for you, show you a little bit about how we work. We’re happy to be in touch with any of our customers as well if you want to reference check us. Please reach out, and we’d love to work with anyone who’s interested.

Jason: Awesome. Kyle, thanks for being on the DoorGrow Show.

Kyle: Thanks for having us, Jason. I appreciate it.

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About Jason Hull

Jason's mission is "to inspire others to love true principles." This means he enjoys digging up gold nuggets of wisdom & sharing them with property managers to help them improve their business. He founded OpenPotion, DoorGrow, & GatherKudos.