The “AI Ready” Myth Holding Property Managers Back During The Holidays

The Holidays Aren’t Always Fair To Property Managers…

🎧 Listen to the Audio Version

The rest of the world is slowing down. Out-of-office replies are lighting up inboxes everywhere. But for property managers? You don’t get that luxury.

Residents are home. They’re hosting families. The heat is running full blast. And suddenly, a tiny issue isn't just a maintenance ticket.  It’s a late-night, full-blown emergency because the in-laws are freezing and the turkey is in the oven.

Now, picture this dream scenario:

The most talented Property Manager you’ve ever met moves to your city today. They walk into your office and say: “I want to start now. I’ll take the holiday shift. I’ll handle the noise while you enjoy your family.”

Would you tell them no? Would you look them in the eye and say, “Actually, come back in six months when our processes are perfect”?

Of course not. You’d grab that chance immediately. You wouldn't let "imperfect SOPs" stop you from getting the help you desperately need.  

You’d trust this person to do a good job based on their skillset.  You’d trust their judgment in stopping before they do something you may not like.  You’d trust their experience to help inform how you could improve your own processes.

Could an AI make that promise? How could I possibly believe it?

That question is the real reason so many PMs believe they “aren’t ready” for AI.

If you can figure that out, then you can develop your own BS meter to cut through the AI cacophony… and maybe find a faster way to spend less time on your phone during holidays.

Vendoroo’s AI agents want to take work off your plate for the holidays. Risk free offer only if you sign up by 12/31/2025.

‍

The Old Belief

A recent post from Peter Lohmann caught my attention. Peter made a thoughtful, grounded point: before rushing to AI, you should first identify the biggest constraint in your business. Constraint theory matters. Diagnose before you prescribe.

I completely agree there.

However, this point caught my eye: suggesting that even the best AI cannot fix broken processes or standards, and that adding AI too early might actually make things worse.

Oof.

That belief is incredibly common.

But today? It’s outdated.

Most property managers using AI today are using:

• ChatGPT, Gemini, Claude, and other generative AI solutions
• AI that was rolled out inside an existing SaaS platform
• AI that automates fragments instead of owning outcomes
• AI that executes instructions without questioning them

In that world, AI absolutely scales dysfunction.
If your standards are unclear, AI just makes the chaos faster.

So yes- MOST AI plugged into incomplete processes can be detrimental.

But as you know, AI doubles in power every six months.  So instead of declaring what AI can and can’t do, let’s challenge our assumptions on it.

The Outdated Assumption

The assumption is that all AI behaves like software.

That it:

• Waits for instructions
• Executes what you tell it to do
• Can't question whether you're telling it the right thing
• Scales whatever you give it—good or bad

If that's your benchmark? Then Peter's logic is sound. You'd better have everything figured out before AI enters the picture.

But here's the thing: the promise of agentic AI is completely different.  It’s built to behave as a teammate.  You just haven’t seen it (unless you’re a Vendoroo client😉), but there are solutions coming out every day trying to deliver on this promise.

So how do you know what to look for?

The Proof is in the Onboarding

Think back to the best hire you've ever made. They didn't just do the job you gave them.

They also:

• Noticed gaps you missed
• Asked better questions than you expected
• Flagged inconsistencies (even when it was uncomfortable)
• Made the work itself better (not just faster)

But here's the telltale sign of a great hire: they made an impact while they were getting up to speed.  They didn't wait 90 days to prove their value. They started adding value in week one.

So here's the question you need to ask any AI provider selling you "agents":

How does your AI make an impact during onboarding?

And they better have a damn good answer. Because if they're telling you it depends on how quickly you do your homework, you're not getting an employee. You're getting software.  It's the difference between hiring AI to run your playbook vs hiring AI to help you build a better playbook.

This is something we had to learn the right way at Vendoroo, but we’re really glad we did (and so are our clients!) Here is what we figured out-

What Agentic Onboarding Looks Like

Like most tech companies we started with the usual onboarding process: lectures about best practices, homework, and meetings to make track your progress.  Just like typical tech our clients were waiting 30-60 days before really feeling results.

That’s when we realized this wasn’t what we set out to create.

We challenged the team to not settle until bringing on an AI agent should feel like bringing on an rockstar employee.  And here is what it looks like now:

• An AI agent looks through your maintenance history and tells you how your actions compare to your SOPs and vendor notes
• The AI receptionist reads your lease, FAQs on your website, and any notes you give it for who on your team handles what calls
• You then have an opportunity to correct what they found or let the agent follow your current practices
• Our team plugs the agents into your existing tech stack (PMS, phone line, Slack, etc)
• The AI starts working for you while you learn how to manage it through a cohort class, watching your peers, and 1 on 1 check ins with an AI coach

See how a Vendoroo AI maintenance coordinator helps your team get better.

Everything is designed to match the expectation of hiring a great teammate, giving them the homework, having them bring you what they found, reviewing it with them, and letting them get to work while you get to know each over time.

Just like a new hire, true agentic AI knows that if it isn’t sure how you like it done, it should “raise it’s hand” and ask before proceeding.  We call these “escalations.”

And we think these “escalations” are vastly underrated.

From “Policy” to Truth

This is where language really matters. Static policies assume clarity already exists.

But burnout hides misalignment.

When teams are overloaded, they don’t fix broken rules. They work around them. They patch, improvise, and move on, because stopping to redesign the system feels harder than surviving it.  Agentic AI changes this because it doesn’t just follow rules.  It holds up a mirror.

Instead of asking your team to explain how things work, the AI shows you how things actually work.

No opinions.
No blame.
Just reality.

And here’s why that’s such a different experience than a new hire, a consultant, or an all-hands offsite:

An AI agent isn’t emotional about feedback.  It doesn’t feel embarrassing for not knowing your preferences.  It doesn’t get defensive when something breaks.  It doesn’t forget the answer once you give it.

When it finds a gap, it raises its hand, asks the question, and then remembers the answer forever.

You don’t have to think through every process in advance.
You don’t have to fix everything at once.
You don’t have to step away from the business to redesign it in theory.

The system gets pressure-tested in real time, while work is happening, in the safest way possible.

That’s the difference between trying to design perfection in a vacuum and letting a tireless, unbiased teammate reflect the truth back to you, one decision at a time.  And when your “teammate” is built to surface reality instead of protecting egos, improvement stops being exhausting.  It becomes guided.

When the system is designed to safely raise its hand every time reality doesn’t match expectations, those moments stop being interruptions. They become the engine of improvement.

Especially when you only answer each question once, and the system never forgets.

The TLDR Non-Obvious Insight

Here’s the non-obvious lesson in all of this:

The common belief in our industry is that you’re not ready for AI until your processes are perfect.  And with most AI, that belief is justified.

Typical AI takes broken processes and makes them louder. Faster. Worse.

But when agentic AI is done right, something fundamentally different happens.

Instead of amplifying process problems, it helps you see them clearly.  Instead of asking you to fix everything first, it helps you improve as you go.  And instead of adding more work to your plate, it starts taking work off of it.

That’s the shift.

The question isn’t whether your processes are perfect.  It’s whether you want help discovering where they actually break, while still getting through the day.

Constraint theory still applies.
Business problems still come first.

But here’s the update:

Modern agentic AI doesn’t require perfect standards to start.
It helps you discover what your standards actually are.

And for an overburdened team, that helps them go from thinking AI is a threat to finding new hope in it.

Especially during the holidays, when the pressure is highest and the margin for error is lowest.

So Back to Your Holiday

That’s why we’re doing something a little different right now.

We’re offering a free, 90-day, risk-free trial of Vendoroo to give property management teams extra support through the holidays.

No long-term commitment.
No requirement to have everything figured out.
Just a chance to experience what it feels like to have an AI teammate that can help shoulder the load, surface the truth, and ask the right questions while your team stays in control.

If you’ve ever thought, “This sounds helpful, but now isn’t the right time,” this is exactly for you.

If you want help ASAP, book a demo here.

Remember that dream PM who walks in and says, “I’ll take the shift”?

You’d trust them because:

• They have the skills to handle it
• They have the judgment to know when to ask for help
• They’re invested in making your operation better, not just getting through the day

Give your team a break on the holidays and let AI take those calls! This is a risk free way to give Vendoroo a try if you’ve ever been curious.

That’s me and my team at Vendoroo- offering to work for you risk free for 90 days.  But the offer is only good until December 31st.

Pablo Gonzalez,

Chief Evangelist at Vendoroo

‍