What Winning With AI Looks Like For PM

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We used to think “winning with AI” meant plugging it in and watching it perform. But during a working session with our Chief PM, David Normand, and Executive Director, Nick Jacobson, we realized something bigger.

AI doesn’t fix your business. It shows you exactly where it’s broken.

And when you treat AI like a teammate, not a tool, something wild happens. You start uncovering the gaps, closing them, and creating a business that runs 85 to 95 percent on its own. That’s when you reach what we call the 5 Percent Club.

Most people are still missing the bigger picture. They think AI is another SaaS tool.

But this is something else. This is agentic AI. A new kind of system that doesn’t just support decisions. It makes them. But to work, it needs context. And that means property managers need a new playbook.

This newsletter is that playbook. Based on our most recent findings, this is what’s actually working on the front lines right now.  But it all starts by answering one question: How should you actually think about this new teammate you're about to hire?

If You Want an AI Teammate, You Have to Treat It Like One

Hiring AI is like onboarding a superstar employee. It shows up smart, experienced, and eager to help. But like any new teammate, it still needs to learn how your business works.

That means asking questions. Lots of them.

And this is where most people slip back into “software thinking.” They expect perfect performance on day one.

But real agentic AI doesn’t work like SaaS. It learns fast, but it needs your feedback to get sharp inside your business.

Every one of those “annoying” questions the AI asks? That’s actually a signal. It’s a cue that says, “Hey, we don’t have a rule for this yet.” And that’s a gift.

Because every time you add a rule, your business gets tighter and smarter. So, what does the process of finding and fixing those rules actually look like in the first two weeks?

PHASE 1: THE FORCING FUNCTION

This Is Where the Mirror Does Its Best Work

For the first two weeks, AI should function as a diagnostic mirror. It doesn't just execute tasks. It shows you every crack in your policies, vendor lists, and escalation paths.

Here’s how the loop works:

• See the decision
• Ask why
• Approve or change
• Codify the rule
• Move on, permanently

This is what it means to work with agentic AI. It's not just about automation.

It's about decision-making. Your AI reaches a fork in the road, checks its training, and if it doesn’t find a rule, it flags it for you.

When that happens, your job isn’t to get frustrated. It’s to say, “Show me the logic,” and then write the new rule together. The moment you do, that rule is baked in forever. The AI never asks again.

That’s not how software behaves. That’s your best-ever employee, absorbing every lesson the first time.

Pro Tip: Run this loop for two weeks. Ruthlessly. It’s your forcing function to upgrade every policy, vendor list, and escalation pathway in your business. The more decisions you fix, the faster you scale.

PHASE 2: THE MULTIPLIER

It’s not plug and play. It’s teach and scale.

This is where the leverage kicks in. Once the AI knows your playbook, it stops asking and starts executing.

What does that look like?

• 60 open work orders now only need 5 to 7 human touch points
• Your team isn’t routing jobs, they’re reading dashboards
  Instead of guessing, you’re optimizing

The numbers get clearer too:

• Percent of work assigned per vendor
• Average days to completion
• Messages per work order

You start spotting trends. You notice when a top vendor is slowing down and you can ask if they’re overwhelmed or just had a bad week. You catch when a vendor is taking 15 messages per job and you can fix the communication gap.

And here's the bigger point. The industry still thinks AI should be judged by how many tasks it can automate. But that’s outdated. The real metric is how many decisions it can own.

That’s what agentic AI does.

It doesn’t just help you do the work.

It does it for you.

WHAT THE JOURNEY LOOKS LIKE

Safe House Went From 40 to 95 Percent. Here's How

Back in December, Safe House was sitting around 40 percent automation. Their policies were loose. One vendor handled everything. Escalation rules were unclear. It was a mess.

By April, they were at 95 percent. Calm. Scalable. Operationally sound.

What changed?

• They customized and committed to SFR policies
• Rebuilt their vendor list with rankings, specialties, and notes
• Tuned routing and receptionist workflows
• Set clear escalation rules
• Embedded their preferences into the system, permanently

Now their broker isn’t in the weeds, and their Ops Manager only steps in for true exceptions. That's the view from the top of the mountain. But...

You Don’t Land at the Top. You Climb

This is a mountain you will have to climb eventually. The only question is whether you want to start now while the path is clear.

We’ve seen the cadence that works.

• Two weeks of closing gaps
• Thirty days of coaching and review
• Thirty more days of refining your system

That’s what it looks like to work with agentic AI. This is not SaaS. This is your last, best hire.

These aren’t guesses. This is what’s working right now across our client base. It’s the latest version of the Vendoroo playbook, and it’s built for property managers who want to get out of the forever firefight and build businesses that scale.  You want a plan that is incremental and easy to reason about.

That is why we packaged this into a simple two-week, thirty-day, thirty-day path you can adopt AI in small steps, see measurable wins each week, and keep climbing with confidence.

It's time to jump on board and join the 5% Club. Hear the simple two-week → 30-day → 30-day cadence here.

—

Pablo Gonzalez,

Chief Evangelist at Vendoroo

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