If AI Can Replace 4,000 Tech Workers, What Happens to Property Management?
Jack Dorsey’s decision at Block is a warning shot for an industry built on repetitive, admin-heavy roles.
Yesterday, Jack Dorsey announced the layoff of 4,000 of his 10,000 employees at Block Inc., the company you are likely familiar with because it owns financial services providers like Square and Cash App. Dorsey didn’t mince words. He directly blamed AI and said that he had two choices: either layoff employees slowly over the next couple of years, or just rip the bandaid off now. Ultimately, the jobs would have to go, because competition will demand it as all of the other FinTech companies roll out the use of AI and eliminate positions themselves.
The question for our industry here is simple: if AI can replace tens of thousands of tech workers, most of whom have what were widely desirable skills until just recently in things like software engineering, then what does that mean for an industry like property management that is heavily operational and admin-driven?
This Isn’t Just About Tech Companies
Yes, tech is leading the way on this. Meta (Facebook), Google, and Microsoft have all recently announced job losses, and it’s not hard to see that this is likely a result of AI boosting efficiencies at their companies. And by “boosting efficiencies” what I really mean in plain language is that AI is taking the jobs that were previously done by humans. There’s just no other way to put it.
The gap between capitalist and laborer might never have been as wide as it is today. Yes, even the industrial revolution which brought literal riots and dead people in the streets as workers clashed with industry robber-barons didn’t compare to what we’re seeing now. The “robber-barons” of yesteryear are now the billionaire CEOs who are creating entire companies on top of an AI infrastructure that will eliminate millions of jobs, and not just at their own companies.
Because the thing to remember here is that AI isn’t eliminating companies or industries; it’s eliminating roles. Or, more accurately, those roles are simply being replaced by AI “agents.” The role is still there, it’s just being handled by a computer instead of by a person. Essentially any role that is repetitive, administrative, or process-driven can be replaced by an AI agent, so long as it doesn’t require “boots on the ground” (and even that will eventually give way once the AI humanoid robots that are currently in development by companies like Tesla are set loose on the world).
It’s easy to see why this is a giant red flag for those of us in property management. Virtually every role in this business is repetitive, administrative, or process-driven. The safest roles right now are those that are driven by human connection, so BDMs and Client Success roles. Everything else is vulnerable.
Where Property Management is Vulnerable to AI
Let’s take a look at this by categories to see where the opportunities are for PM companies to replace humans with AI:
Leasing
AI text and voice to handle lead inquiries
Automated scheduling of showings, even if not using self-showing lockboxes
AI automatic application screening
Automated lead nurturing
The only human you need is basically the person who goes out to take photos, put up signs and lockboxes, and do inspections. Everything else can be handled by AI. And you’ll also notice that every one of those tasks can be outsourced if you don’t want in-house labor. Depending on your market and your operation, outsourcing the boots-on-the-ground portion might be more cost-effective than having an employee.
Maintenance Coordination
AI triaging & troubleshooting of service requests
Automatic vendor selection & dispatching
Predictive maintenance analytics
We’ve all seen the AI companies out there who have already rolled out solutions to this over the past couple of years. There are the companies doing it smartly in my view (Property Meld), and then there are the companies who I think have been recklessly irresponsible with their rollout and promises (*cough*Vendoroo*cough*).
But this is no longer something that relies upon a SaaS vendor’s framework. You can literally build yourself an AI maintenance coordination agent in OpenClaw now in a matter of hours, trained specifically on how YOU want things to work. The complaints about the SaaS provider’s algorithm for vendor selection? No longer important. Just have the AI create you your own algorithm based on your own instructions. And again, this takes literally only hours.
Bookkeeping & Accounting
Automated rent collection follow-up
AI reconciliation of bank accounts
Automated invoice parsing & entry
Detailed financial analytics in seconds
Sure, you’ll still need someone to do the high level financial decision making. But for many small to medium sized PM companies, that’s just the CEO/broker. All of the other daily routine bookkeeping work can be done by AI.
Routine Owner & Tenant Communications
Automated AI responses to common questions
Automated handling of tasks like sending out eviction notices, creating leases in the PM accounting software, processing lease renewals, etc.
Automated quarterly account reviews
What once took one employee per 100 doors will now take one employee per 1,000 doors. The only thing the Client Success Manager or Resident Service Manager (or whatever you call these roles) needs to do is the high level decision-making work that the AI can’t quite do yet (or wouldn’t be wise to let it do in light of licensing laws in most states). And the AI can automatically escalate those matters to the human so that you’re not having to constantly monitor it.
Will Property Management Lay Off 40% Too?
I’m not going to mince words with you here: yes. The answer is yes. The only question is timeframe, not outcome. In fact, 40% is way on the low side. I suspect it’s going to be something closer to 80% when all of the dust settles.
That said, there are differences here that will make it take longer in our industry than it is in tech, which is where the bloodbath is already starting. Unlike tech companies, property management is operationally complex. Which is the same reason that no giant corporation has ever been able to come along and roll up the entire industry to create a near monopoly. Operational challenges vary not only state-to-state, but county-to-county, and even city-to-city. Training an AI to handle all of that isn’t as simple as just telling it the functionality of the app that you want to create and then letting Codex write all of the code for you. The various permutations of just how an eviction can go would take a whole lot of work to properly train the AI, let alone all of the other functions we do.
In addition, human judgment is sometimes required. Conflict resolution is still a very human endeavor. While AI is actually pretty damned good at making recommendations for you about how to diffuse a volatile situation, it isn’t good at actually delivering that communication to people in a way that will diffuse things. People still don’t like talking to robots, so a perfect message delivered by AI will not be received in the same way as an imperfect message delivered by a human. At least for now. The way we’ve seen all of this tech play out is that new generations get more and more comfortable with it. For example, my father wouldn’t even consider giving an AI his personal information to do tasks for him. He’s from a generation that zealously protected things like their SSN and refused to even give them to a person, let alone a machine. But a Gen Zer? Trust me, they have no qualms about giving an AI their personal details if it will get things done more quickly and easily for them.
So the answer is an unequivocal yes. Property management companies will end up laying off most of their employees, it’s just a matter of when. That NARPM Benchmark of 60 doors per direct employee is about to be a thing of the past. It may only be 100 doors per employee in the next 18 months, but then it will 200. And then 300. And it isn’t going to stop there.
From Labor-Heavy to Tech-Enabled
Tech-centric PM companies have never worked out. We can go back a decade or more to Castle Property Management, which ended up burning through millions of investor dollars in a pre-AI world trying to make property management a primarily tech-based play, or we can look at more recent examples of the same idea that are still waiting to IPO this supposedly groundbreaking tech replacement for property managers. So I don’t think we’re going to end up in a world where property owners and residents are only talking to AI and there’s just a broker sitting at the top of these AI agents making all of the money. But we are shifting to a new world where labor-heavy processes are replaced by tech-enabled high-level labor.
Where I think this is all heading is to an industry where day-to-day tasks are handled by the AI, along with most routine communications, and then decision-making, relationship building, and high level conflict resolution are handled by experienced humans. And those experienced humans will use the AI to assist them with their role.
Human staff will continue to be necessary for:
Sales (at least at the closing level)
Relationships
Owner & resident retention
Complex decision-making (like whether to accept a legal settlement or not)
Boots-on-the-ground grunt work
Aside from that, five years from now, I don’t foresee humans doing a lot of the process-driven work that they’re doing today at all but the most boutique of PM companies.
The Risk for Small PM Companies
This newsletter is predominantly for PM companies managing 1,000 doors and fewer, so let’s focus on that segment and ignore the “big boys.” This is where it gets really interesting.
Those large players are going to be dumping enormous amounts of money into AI to reduce payroll and expand aggressively after cutting costs and prices. Some of these players (think PURE Homeriver) have already been heavily tech-focused since their founding, and this is just the next iteration of technology.
This leaves those of us in the small-to-mid-sized realm competing with companies who have millions of dollars to deploy in AI development. That sounds scary.
But the truth is, it’s not really all that scary. The weird paradox of AI is that it’s somewhat of a great equalizer. AI is dirt cheap. I use it quite a bit in my PM business, and I still only spend a few dollars a month in AI data processing. When you look at OpenAI’s fee schedule, for example, it looks very confusing and intimidating. After all, what the hell is a “token,” anyway? But when you actually start using the tech, even for data-intensive things like deep research and coding, you realize that each thing you’re having it do is only pennies in cost. Coding that would have cost you tens of thousands of dollars from human software engineers can be done for a few dollars and in a tiny fraction of the time. The AI will even test its own coding, find errors, and correct them. Or, better yet, you can have one agent who does the coding and another agent on a different LLM double check the first agent’s work.
So, while these big companies have nearly limitless money to spend on AI development, the truth is that they really don’t need all of that money for that. The big lift is actually being done by the AI companies like Anthropic and OpenAI, and their technology is available to you the same as it’s available to Evernest and their 20,000+ doors.
So the real risk isn’t that the big players can destroy you with their massive AI investment. The real risk is that you simply rest on your laurels and don’t use the tech that’s available to you because you don’t understand it or are taking a principled stand against AI. I promise you, I understand the principled stand. I don’t like the sound of a world dominated by AI, either. But that world is upon us, and if you don’t adapt to it, it will sink your business.
Ultimately, AI won’t eliminate property managers. But property managers who use AI will eliminate the property managers who don’t (or won’t).
What to Do Right Now
It’s time to get started on this if you want to be one of the PMs who survives and thrives after the AI invasion. And I don’t mean that you need to go out and sign up for a bunch of new AI SaaS solutions. But you do need to start getting ready for the big change.
First, start working on identifying the repetitive tasks in your PM business. Figure out which workflows are almost entirely done on a computer and require no human to step foot in a house. Keep a list of those tasks, because that’s what you’re going to start working on transitioning to AI.
Next, start researching AI. I want you to be watching so much AI educational content on YouTube that the algorithm starts only recommending you AI related content. Your start page in YouTube should be nothing but videos talking about AI.
Next, put off any plans for hiring new employees. Instead, when things start to get busy and you’d normally start looking for an additional human, automate with AI some of the things that your existing humans are doing. The technology is already there for it.
Finally, it’s time to start re-skilling your staff to work in this new environment. The employees who are going to be needed in the future are those who have people skills. In other words, it’s a good thing that I’m the owner of the business instead of the employee, because the business otherwise will have absolutely no need for introverted semi-autistic nerds like me who hate small talk. The business needs customer-facing employees who have high emotional intelligence and can resolve conflicts as smooth as butter. Existing employees who are mostly doing administrative work will need to be transitioned into more customer-facing work as you grow and that admin work no longer requires a human.
To be clear, I am not advocating for you to build a bunch of AI and then lay off 40% of your workers like Dorsey did. While I can’t really say that I blame him, I also don’t really like what he did. I’m a former labor union leader, and that’s ingrained in my psyche. I simply cannot toss humans aside like Dorsey can. But I certainly can plan on hiring a lot fewer people in the future as we grow. And that’s what I do encourage you to start planning for. Keep your employees. But transition them to more relationship-based roles as you roll out the AI. This actually creates new opportunities. Instead of employees spending all of their time doing rote repetitive tasks like filling out lease forms and reconciling bank accounts, they can have one-on-one conversations with clients and residents. If you handle this right, you can watch your NPS or CSAT soar.
Final Thoughts
I’m not going to sugarcoat things. I see mass structural unemployment as an inevitable problem on the horizon that policymakers are going to have to deal with. And it’s coming much faster than many people think. But I’m also not going to be so doom-and-gloom as to tell you that property management is going to die as a business as a result of AI. One way or another, government will have to see to it that the average person can afford to live, and the average person is going to need a place to stay. Our industry is not going away. But it is definitely going to evolve. Our industry has always been on the trailing edge of technology adoption. I still talk to PMs who are keeping paper files and organizing processes on white boards or spreadsheets. This time, with this technology, that hesitancy to adapt could be quite costly. Don’t get behind. Recognize where things are heading now, and start to prepare for it. If you do that, you’ll be ahead of most of your competitors who are still keeping their heads thoroughly covered in sand.
Open to Work
Are you an experienced PM industry employee looking for work? Or are you a PM company or vendor seeking the best talent? Send me your info and I’ll feature it here!
Each week we also feature a Remote Team Member available through VPM Solutions. See this week’s below! Click on the image to get more info:
Newsletter Stats
Here are our statistics for the last 30 days:
73,028 impressions
41.79%% open rate
Issue with the highest readership:
“The Giant Squeeze: Why 2026 Will Separate Professional PMs from the Rest”
7,602 impressions
Looking for Advertisers!
We always have ad slots available for industry vendors. Sign up for an ad or ad package here. Pricing and ad details can also be found at that link. Questions about advertising? Email abio@propertymanagerassist.com or book a time here.
Debate Me
Disagree with my take here? Have a different perspective? There’s nothing I love more than a good debate or even just an intelligent conversation. If you’d like to jump on a podcast recording with me to discuss this topic, please let me know!
The views expressed in this publication are the views of the author only and not any advertisers, sponsors, partners, affiliates, or organizations that the author may be a member of.