At first, automating invoice processing and vendor payments feels like a dream. You’re speeding up invoice approvals, doing less data clean-up, and writing fewer checks. As time passes, though, small glitches often begin to surface. You start to wonder if you made the right choice with your accounts payable (AP) automation solution.
Over time, you begin to realize that not all AP automation tools are built to scale with your real estate business or adapt to changing needs. Like any relationship, companies can simply outgrow systems as well as the vendors supporting those systems.
Here are four red flags you shouldn’t ignore with your current AP automation solution. If left unaddressed, they can create more work, increase risk, and limit AP’s contributions to the business.
1. Invoice Processing is Less Automated Than You Thought
Maybe you started with your current AP automation partner when you only had a few properties, but you’ve grown substantially since then. Now, your invoices come from many different vendors and locations and cover a wider range of expense types. This complexity requires extremely flexible and customizable invoice approval workflows since different stakeholders need to be involved in approving invoices, depending on what they are for. Here are some of the specific approval workflows you might need:
- Route invoices by location or Property ID: invoices in the Midwest need to be approved by the Midwestern regional manager before coming to the AP manager
- Route invoices by GL code: invoices with GL codes related to capital expenditure (CapEx) need to be seen by both your Project Manager and Director of Asset Management
- Route invoices based on certain exceptions: invoices that don’t have an associated purchase order (PO) or contain a mismatch with the price on the associated PO must trigger an exception-based approval workflow that routes the invoice to the right stakeholder (like procurement or the requesting department) for review and investigation.
If the invoice processing functionality in your AP tool can’t handle these more complex routing and approval needs, you might need to use workarounds or, worse yet, revert to emailing invoices around to colleagues for final signoff. As invoice approval timelines extend, it can push payment dates out, which puts you at risk for late payments and frustrated vendors calling you to ask about their outstanding payments.
Certain AP automation solutions understand the varied routing needs of real estate companies, however, and offer robust invoice approval workflow capabilities to match them. They also make managing these workflows extremely easy. Without specialized training or help from IT, users can adjust workflows, copy existing workflows so they don’t need to start from scratch when creating a new one, see the projected workflow an invoice will go through, and pull reports about what approval workflows are being used.
With these solutions, real estate companies can set up these solutions to match their specific structure, rather than adjusting how they do things because the software can’t support it.
2. You Question How Secure Things Really Are
You likely wanted to automate your invoice processing and payments to increase the security of your AP, at least in part. Consider this: 79% of organizations were victims of payment fraud attacks and/or attempts in 2024, per the AFP Payments Fraud and Control Report 2025.
In many ways, your current AP automation provider may be doing and saying the right things to help you in this arena by offering features like automatic detection of invoices that are duplicates or near-duplicates, so slightly altered copies of legitimate invoices don’t slip through unnoticed. The provider is also probably hyper-focused on converting your vendors from easily manipulatable paper checks to more secure payment types, like ACH and virtual card, which are much harder to intercept and steal.
But if concerning signs begin to emerge about your AP provider’s security (or lack thereof) – either in the news, heard from peers, or from other vendors – it’s worth taking seriously and investigating further. Problems might include failure to notify you of (or to even notice) a compromised supplier, suspicious invoices being uncovered only after the system has finished ingesting them without warning, or reports that other businesses using your same AP automation solution have been compromised in some way.
These kinds of incidents can signal trouble ahead.
You should be able to have frank conversations with your provider if a security incident ever occurs, or if specific questions arise related to security protocols or fraud prevention. They should be able to give you details around the scope of what’s happening, what’s being done to address the problem, and how they are working to ensure the security of your data, your vendors, and your invoices and payments moving forward.
Should your provider’s answers prove insufficient, it may be time to investigate other security-first AP automation and payments technologies in the market. Here’s a starting point of what to look for in terms of fraud prevention:
- Strong vendor vetting process – Ensure the provider authenticates vendors attempting to join the payments network against many different data points, so that fraudsters are blocked from gaining access. Examples might include verifying that the vendor’s tax ID matches the data in third-party databases, or ensuring that the location they’re enrolling matches the address of the business. It can be helpful to take a look at the provider’s existing vendor network to understand how many vendors have already been vetted and verified and are ready to transact with you immediately; this can impact how much of a running start you’d have by using them, plus better security.
- Real-time fraud monitoring – The payments network should perform continuous automated checks for suspicious log in times, unusual devices, potentially fraudulent account change requests, and other markers. If there’s a red flag, there should be a specific action plan in place, such as preventing that specific user from logging in and alerting a team of specialists to review said access attempt, so that the situation doesn’t escalate to outright fraud.
- Controlled account access – Access to the AP automation tool itself should be protected with multi-factor authentication, requiring users to provide two or more forms of identification before they can access it.
- Secure storage of vendors’ bank account information – You don’t want to be responsible for storing bank account data for your vendors who receive ACH payments, or updating that data when they want to change bank accounts. Ensure your AP automation provider allows vendors to input and manage their own bank account details via a highly secure vendor portal, and that this bank account data is stored behind multiple layers of protection (e.g. account tokenization and multi-factor authentication) so fraudsters can’t access sensitive data and systems.
3. Technical Support and System Up Time Are Falling Short
If a property ID isn’t mapping correctly to invoices, or one of your vendors is having trouble enrolling in your electronic payments offering, you may need to call your AP automation provider’s technical support team.
Ideally, a rep is reachable via phone or chat without excruciating wait times. Once connected, your representative can see all the same information you’re seeing, knows how all the back-end parts work together, and can help you fix the data mapping issue painlessly and professionally.
On the vendor enrollment side, a knowledgeable onboarding specialist should be able to talk the vendor through the steps to start receiving payments electronically, anticipating where there might be questions, handling objections masterfully, and reaffirming why that vendor should be enrolling in that specific payment type.
Your solution should also be running without hiccups or unplanned outages. How else can you expect to handle the huge influx of summer turn invoices from your student housing properties in late July/early August? What about when you need to get several payments out to your plow company for a recent bout of heavy snow?
If your experience looks more like the below, however, you should be wary of your provider’s ability to help you.
- Support is slow or unresponsive: You and your vendors must wait forever for calls to be picked up or for support tickets to be acknowledged. You have no real sense of how long it’ll take for an issue to be resolved.
- Support doesn’t grasp the context or understand your business: You often spend more time explaining why you’re trying to do something in the tool, when the support specialist should have the support skills of a Jedi. If it feels like support reps don’t understand the ins and outs of how real estate AP works and lack the know-how to configure the solution for your needs, it’s time to upgrade.
- Software outages are common: Your AP system is going down unexpectedly and/or you’re experiencing service spottiness. There are limited explanations as to why such things happen repeatedly, or what the plans are for fixing it in the future, impacting your ability to get day-to-day tasks done.
4. You Don’t Know Where the Product is Headed
Your business is constantly evolving, with new properties coming online, shifting regulations, increased reporting needs, and higher expectations from leadership and stakeholders. You need technology partners who can keep up, not ones who leave you wondering what’s coming next.
A strong AP automation provider should have a clearly defined product roadmap that not only supports your current needs but also anticipates what’s you’re going to need in the future, whether that’s smarter and faster invoice ingestion and coding, expanded integrations, or even more sophisticated fraud detection and prevention tools that lock out the savviest of AI-enabled fraudsters.
If your current provider is vague about future enhancements or releases, it may be a sign they’re either not building with your business in mind or that they’re not even sure where things are headed for themselves. Keep an eye out for these happenings as well:
- You ask for the same features repeatedly and receive no timeline or follow-up.
- Features that don’t align with real estate get prioritized over ones that do, despite their stated focus on your industry.
- You’re not kept in the loop on conversations about product roadmap and development, and it’s tough getting a list of new features.
Find a provider who you know – and can tell – values your partnership and keeps you abreast of where the product is headed, inviting you to help shape the direction. Without this visibility and collaboration, you’re left guessing about what’s coming next, and there’s no telling if your solution will keep up with how fast you need to move.
AP Automation Should Make Your Life Easier, Not Harder
Take a critical look at the AP automation and payments provider you’re already using. You’ll be assessing for a match with the needs of your growing real estate company. It is an undertaking. But ignoring warning signs, such as those outlined above, and “sticking it out” with something that just isn’t working can leave you in a bind. Not only can it introduce hidden complexities, costs, and risks, but it can also wear down your AP team and your vendor relationships.