How do maintenance demands change when you shift from a single-family rental portfolio to a high-density multifamily community?

In this episode, Pablo Gonzalez sits down with operations insider Frank Barbarena from Highmark Residential and Connor Hassett from Vendoroo for an open dialogue comparing these two worlds. On paper, the software systems look about 80% identical. But on the ground, the workflows require a completely different approach.

You'll Learn:

🔀 How single-family vendor management differs from managing an on-site, in-house team
👥 Why prioritizing your crew's daily work experience directly reduces employee turnover
🚨 Using AI to shield techs from midnight false alarms while maintaining a high-quality resident experience
⚡ How modern property automation completely wipes out daily manual friction

🎧 Listen now to discover how to automate your backend busywork and buy back the time needed for true customer connection.

🌟 Stay Connected with Us:

🤝 Connect with Frank Barberena on LinkedIn
🤝 Connect with Connor Hassett on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:40 — Challenging The Resident-First Mentality
03:59 — Vetting AI For Multifamily Demands
06:28 — Multifamily Vs. Single-Family
09:44 — Quarterbacking Maintenance via 24/7 Phone Triage
11:37 — Blueprint of the 48-Hour Ticket Window
11:59 — The Manual Reality of the Property Supervisor
12:31 — Stripping the Complexity from Mobile Work Orders
13:59 — Automating the Front Desk with 24/7 Phone Reception
15:11 — The White-Glove Approach to Human-in-the-Loop Automation
15:53 — The 50% Rule: Filtering Real Midnight Emergencies
16:09 — A Team That Has Thought Out Maintenance
18:07 — Why This Must Be Everyone’s True First Priority
22:48 — Live Demo: Stress-Testing the AI Voice Agent
29:23 — Erasing the Backlog with 30-Second Text Troubleshooting
35:14 — Training AI Like a Local Crew Member
40:07 — The Command Center: Managing by Exception
48:47 — The Real Top 5 Reasons Techs Quit
49:29 — Streamlining Complex Unit Turns
54:09 — Using AI to Protect the Human Experience

Touching every ticket used to look like ownership.
Now, it can keep your maintenance team tied to the old way of working.

Pablo Gonzalez, Chief Evangelist at Vendoroo, breaks down the new maintenance scorecard - protect the experience, improve the system, and catch embers before they become fires.

You'll Learn:

🤖 Why ticket activity is no longer the best measure of maintenance performance
👀 How the coordinator’s role shifts from touching every task to watching the system
🔥 Why protecting staff capacity helps teams catch resident frustration earlier
📊 How to build KPIs around the workflow your business actually runs
🧠 Why teaching the system your judgment makes future maintenance decisions stronger

🎧 Listen now to see how AI-native autonomous execution gives maintenance teams the space to focus on the experience, not repetitive work.

🌟 Stay Connected with Us

🤝 Connect with David Normand on LinkedIn
🤝 Connect with Rob Kazen on LinkedIn
🤝 Connect with Chris Weidley on LinkedIn
🤝 Connect with Stacia Davis on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

0:11 – The Hardest Part Of AI Adoption
01:47 – When Activity Starts Becoming Interference
03:06 – The Scoreboard Built For Manual Maintenance
05:10 – The Human Work That Still Matters
07:10 – The Hidden Cost Of Just Handling It
09:29 – Freshness As A Maintenance Advantage
11:22 – A KPI Cannot Be Copy And Pasted
13:24 – Teaching The System Your Business Judgment
16:13 – Measure The Work AI Makes Possible

Think 60% AI automation is the limit for property management? Think again.

In this episode, we are sharing the webinar replay featuring David Normand, Pablo Gonzalez, Brian Bean (Broker/Owner of Dream Big Property Management), and Kogi Hoyos (Operations Manager at Dream Big).

Dream Big broke through a 60% ceiling to reach 90%+ maintenance automation by treating their AI as an employee, not software. If you are already getting value from AI but suspect your team hasn't unlocked its full potential, this masterclass is exactly why you need to tune in.

You'll Learn:

📉 How to break through operational ceilings keeping teams stuck at partial automation
🧠 Why treating AI as an internal employee transforms trust and software compliance
⚙️ The exact framework to pivot from daily fires to global scalable systems
📊 What logic logs do to shift your maintenance workflow to trust-but-verify
🏖️ How system optimization eliminates manual tasks, lowering stress to buy back time

🎧 Listen now so you won't miss what achieving 90%+ automation actually looks like in practice.

🌟 Stay Connected with Us:

🤝 Connect with Kogi Hoyos on LinkedIn
🤝 Connect with Brian Bean on LinkedIn
🤝 Connect with David Normand on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 — The 60% Automation Ceiling Trap
07:42 — Why Knowing the Software Inside and Out Still Left Us Stuck
10:36 — Crushing Industry Averages Even With Underutilized Automation
12:47 — The Real Cost of the One Minute Maintenance Call
15:48 — The True Promise Of AI Is Carrying The Burden
16:16 — Treating Your AI Like A New Hire
17:13 — How High Automation Scales Resident Satisfaction
18:46 — Detaching From Daily Operations to Focus on Portfolio Growth
20:18 — Breaking the Cycle of Shifting the Operational Burden
23:21 — Realizing Ninety Percent Automation Is Possible Through Peer Proof
27:00 — Breaking the Third Party Vendor Mindset in the AI Era
29:45 — Why Investing Time Training ROO Guarantees High Automation
30:49 — Stopping the Mind Reading Expectation With AI
32:26 — Scaling System Changes Portfolio Wide in Thirty Seconds
34:54 — Separating Property Context From Global System Policies
37:43 — How to Instantly Uncover the "Why" Behind a Vendor Assignment
39:34 — Moving From Constant Supervision to Trust But Verify
41:02 — When AI Communications Are Clean Enough to Mimic a Human
42:34 — From Third-Party Vendor to AI Employee
44:06 — Visualizing the "Up and to the Right" Shift in Automation Data
53:44 — Betting Big on Human-in-the-Loop Support
59:06 — Taking Off the Emergency Brake: Letting the System Drive
01:01:29 — Product Sneak Peek For Broker-Owners
01:06:51 — The Ultimate ROI: Buying Back a Sunday Off

When the world is rapidly automating with AI, this property manager is leaning into something that will always deliver value- the service mindset.

In this episode, Pablo Gonzalez, Chief Evangelist at Vendoroo, is joined by Thomas Patchin of Real Property Management Peace, to prove that automation doesn't take away from personal connection. Together, they show how top operators use smart AI assistants to handle backend tasks to put true service back at the center of your business.

You'll Learn:

🤝 Why connecting deeply makes prospects feel understood
❓ What questions to ask to uncover true intentions and pain points
🎯 Shifting away from traditional property management
🤖 Freeing property managers of manual work to achieve deeper human connections.

🎧 Listen now to discover how to automate your backend busywork and buy back the time needed for true customer connection.

🌟 Stay Connected with Us:

🤝 Connect with Thomas Patchin on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters: 

02:01 — The Power Of Authentic Connection In Sales
04:33 — Using AI To Have More Conversations, Not Less
06:44 — Understanding Pain Points To Close Deals
07:57 — Navigating Competing Priorities of Stakeholders In Property Management
10:01 — Uncovering Why An Investor Is Calling
12:23 — Why Making People Feel Understood Matters More Than Your Sales Pitch
17:35 — Using Self Deprecation To Break The Ice On Discovery Calls
19:44 — Designing Question Trees That Reveal True Client Priorities
23:54 — Business Development Through An Active Service Mindset
29:44 — Measuring Success Through Impact
30:53 — Replacing Task Clutter With High Value Conversations
34:27 — Why The Future Of AI Is Still Service
38:23 — Differentiating Your Operations Beyond Generic AI Wrappers
40:11 — Human And Technology In Delivering Custom Client Experiences
41:50 — Using AI To Give Property Owners Exactly What They Want
43:52 — The Industry Shift Creating Demand For Boutique Property Management
45:43 — Building Deep Market Niches Beyond Standard Property Management
49:27 — Breaking Traditional Property Management To 10X Your Value Stack
51:17 — Showing Up In The Service Of Others
55:55 — From Customer Relationship Management To Relationship Development
57:52 — Voice Tech Is Shifting From A Simple Tool To Your Biggest Differentiator
01:02:11 — The Completeness Of An AI Solution Means Better Human Conversations

The 2026 Property Management Trends Report 2026 just came out.

And while everyone is rushing to dissect how AI is rewriting owner behavior and expectations, the conversations around it are focused on the wrong metrics.

In this mini-episode, Pablo Gonzalez, Chief Evangelist at Vendoroo, dives deep into the raw data. He details the obvious trends around speed and expectations but uncovers ONE BIG THING that the data is showing us. Once you see it, it will make total sense to you. And it's shocking that nobody's talking about it!

You'll Learn:

🤖 Why tracking surface metrics forces you to chase market symptoms rather than the actual root cause
📉 Moving past speed to understand what a fast response actually signals to a client
🧠 Unpacking a hidden statistic that uncovers the top emotional driver for hiring a PM
🤝 How forward-thinking operators leverage live agentic AI inside their sales pitch to win competitive accounts
🔄 How shifting your maintenance workflows to a deep delegation framework that scales capacity up to 1,500 units
🎯 Why future market winners will focus entirely on delegation to sell certainty

Download the PM Trends Report HERE

🎧 Listen now so you won't miss what the PM Trends Report 2026 is actually telling you.

🌟 Stay Connected with Us:

🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

0:00 — The 2026 PM Trends Report is Out
01:58 — Obvious Takeaways Everyone is Discussing
02:46 — Using AI To Find The Best Property Managers
03:52 — Landlords Value Tenant Experience Over Short-Term Cash Flow
04:47 — The Misleading Focus On Response Times
05:42 — What Owners Really Demand Beyond A Faster Work Order
06:17 — The Number One Reason Owners Hire a Property Manager
07:07 — Owners Want Fewer Problems Reaching Their Desk
07:45 — How Smart Operators Use AI As Their Differentiator To Win New Accounts
09:51 — What Landlords Actually Feel When They See AI Working
11:50 — Why Property Managers Must Trust Their Own Technology First
12:41 — The Difference Between Halfway Automation and Real Delegation
14:23 — Real Stats from the Dream Big Property Management Case Study
16:22 — Redefining the Operational North Star for Future Winners

If you are still staffing your maintenance department based on the old 200-door per coordinator benchmark, you are missing a massive opportunity to scale your business and reclaim your team's time from a 24-hour firefighting loop.

Pablo Gonzalez, Chief Evangelist at Vendoroo, and Nicholas Jacobsen, Executive Director, break down the new maintenance math and explain how shifting to agentic AI takes the repetitive work completely off your staff's plate, allowing PMCs to scale up to thousand doors.

You'll Learn:

🤖 Separating basic software functions from true autonomous workflows
📈 Scaling your door count without increasing human headcount
🔧 Moving high-volume administrative tasks entirely off your staff's plate
🛡️ Filtering out maintenance requests automatically through resident troubleshooting
🛑 Defusing internal staff fear and protecting team culture
📅 Training your system like a teammate instead of configuring software
🌲 Shifting human focus from task firefighting to relationship management

🎧 Listen now to discover how to update your maintenance math, scale your door count, and reclaim your operational freedom.

🌟 Stay Connected with Us:

🤝 Connect with Nicholas Jacobsen on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

02:26 — Agentic AI Vs. Generative AI
05:09 — The Old Math Of Maintenance
08:02 — The New Math Of Maintenance
12:44 — What The New Math Actually Means
15:00 — From Managing The Trees To Managing The Forest
18:39 — Leveraging Real Time Data For Better Resident Experience
24:25 — Mistake #1: Treating Agentic AI As A Software Implementation
29:12 — Mistake #2: Babysitting Agentic AI
31:44 — Mistake #3: Employee Sabotage
34:27 — Vendoroo Had To Own The Outcome First
37:05 — Automate Towards People, Not Away From Them
37:59 — De-Risking AI Implementation
40:31 — Using ROO As Your PMC's Differentiator
41:39 — The Need For Human-In-The-Loop During AI Implementation
43:35 — How ROO Closes A Work Order
47:29 — Where ROO's Knowledge Comes From
51:44 — ROO's Integration Capabilities With Meld
53:12 — How Resident Sentiment Feature Works

500+ agentic AI rollouts into it, and ROO has shown us the same 3 mistakes keep being made:

- Treating an agent as software
- Turning it on to scale chaos
- Unnecessary internal sabotage

In this episode, Pablo Gonzalez, Chief Evangelist at Vendoroo, shows you why these mistakes are being made and how to avoid them.

You'll Learn:

🔧 Why owners churn when maintenance creates stress, not just when returns drop
⚡ How AI speeds up responses, troubleshooting, and vendor dispatch
🎯 How AI adapts workflows by property, owner, and resident
🤖 The difference between AI that helps and AI that handles the job
🚨 Why software thinking, interruptions, and fear can break adoption

🎧 Listen now to learn how the best property management companies build trust in AI, accelerate maintenance operations, and create teams that embrace automation instead of resisting it.

Want to see how to avoid these mistakes in real time? Register for our upcoming webinar on Thursday, June 11 at 3 PM EST and see how to break through these exact roadblocks to hit 90%+ automation!

REGISTER HERE: https://us06web.zoom.us/webinar/register/3617805667417/WN_gwDCizSpR0qFn3WfWtpGZA#/registration

🌟 Stay Connected with Us:
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

02:29 — Why AI Feels More Overwhelming Than Ever
05:40 — Vendoroo's Track Record Across 500 Deployments
06:39 — Securing Team Buy-In For Safe AI Adoption
07:39 — The Core Thesis Behind Play Bigger
08:58 — Why Churn Gets Worse As You Scale
11:30 — Brian Rosenthal's Ten-Year Portfolio Exit
12:34 — Pablo's KTA Story And Investor Churn
15:29 — What Owners Really Want According To PM Trends
16:10 — Ending The Three-Hour Work Order Investigation
17:05 — How AI Troubleshoots Maintenance Around The Clock
18:59 — Creating Owner-Specific Maintenance Workflows
23:36 — Generative AI Versus Agentic AI
25:24 — Why Legacy Software Breaks In Modern Workflows
26:59 — The Four Paths To Agentic AI Adoption
28:48 — What 500 Deployments Reveal About Maintenance
31:09 — Risk One The Software Mindset
36:24 — Risk Two Interruptions Kill Momentum
40:34 — Risk Three Fear Leads To Sabotage
47:45 — The Story Behind Automating Toward Humans

Your team can’t answer every maintenance request in 15 seconds.

But residents are starting to expect it. Owners still want updates, vendors still need coordination, and your staff is already buried trying to keep the workflow moving.

In this mini episode, David Normand and Robert Dell’Osso break down why the next generation of owners, residents, and operators are forcing property management companies to rethink how work gets done.

You'll Learn:

🔍 Why software fails when it’s bought before the constraint is clear
⚡ How owner and resident expectations changed the definition of efficiency
📱 Why texting is becoming the new front door for maintenance
🧠 Where form-based AI stops and agentic AI starts
📊 Why off-platform communication creates operational blind spots
🤝 How AI moves teams from task management to human engagement

🎧 Listen now to understand where maintenance operations are headed- and what it takes to meet the service standard owners and residents already expect.

🌟 Stay Connected with Us
🤝 Connect with David Normand on LinkedIn
🤝 Connect with Robert Dell’Osso on LinkedIn
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬 Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:45 – Why Technology Fails After The Demo
01:15 – The Shiny Object Trap In Property Management
02:02 – Keeping Up With The Context Shifts
02:17 – What The New Level Of Owners Expect
02:41 – The One Business Day Standard Is Dead
02:41 – The New Standard Is Not Just Speed
04:10 – Texting Reveals A Bigger Service Shift
06:19 – Where Form-Based AI Reaches Its Limit
07:40 – Off-Platform Communication Kills Visibility
08:26 – Let ROO Own Maintenance
09:42 – Set It, Forget It, Be Human
10:02 – Humans Had To Own The Outcome First Before AI

Maintenance runs 24/7.
It does not wait for office hours. And owners do not trust a process they cannot see.

That is why the shift from operator-managed coordination to AI-native autonomous execution.

In this conversation, David Normand (Chief PM of Vendoroo) and Marc Cunningham (CEO of Grace Property Management & Real Estate) break down how ROO turns maintenance from a reactive bottleneck into a controlled, around-the-clock workflow- and what becomes possible when AI stops generating answers and starts helping operators make decisions.

You’ll Learn:

⚙️ Why office hours no longer match resident expectations
🤖 How ROO moves beyond rigid troubleshooting
🧠 Why your best maintenance logic cannot stay trapped in one person’s head
📲 What happens after the resident submits the request
📈 What today’s automation numbers reveal about maintenance scale
🛡️ Where AI still needs human support

🎧 Listen now to hear how agentic AI helps property managers stop sleeping next to the emergency phone and start building a maintenance operation that works around the clock.

🌟 Stay Connected with Us

🤝 Connect with David Normand on LinkedIn
🎙️ Connect with Marc Cunningham on LinkedIn
📬Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 Show Kickoff
02:01 Meet David Normand
02:33 Northeast PM Challenges
03:38 Bravado And Candor
05:51 Getting Into Property Management
07:04 Scaling To 600 Doors
09:18 Burnout And Going Big
10:31 FedEx Workflow System
12:45 From PM To AI Maintenance
16:41 Vendoroo Automation Today
19:23 How The AI Handles Calls
21:37 Instant Work Orders
21:57 AI Maintenance Texts
22:41 July 4th Washer Save
24:44 Smart Tips From Data
25:34 Custom Workflows Context
27:11 Vendor Selection Logic
28:14 Owner Trust Reporting
31:40 Scheduling And NTEs
33:05 Reviews And Vendor Chasing
34:10 AI Maturity Journey
35:46 Two Takeaways For PMs
37:05 Guarantee And Accuracy
37:39 Where To Find Vendoroo
39:17 Final Advice On Edge Cases

If you are treating net operating income as your ultimate defense against owner churn, you are banking on a metric that 92% of rental property investors say they are willing to sacrifice for a better experience.

The gap between delivering returns and keeping owner trust has never been clearer.

Pablo Gonzalez, Chief Evangelist at Vendoroo, breaks down the new PM Trends Report from Jordan Muela and Peter Lohman and the propertymanagement.com Maintenance Software Report - and the bigger story they begin to reveal when viewed together.

You'll Learn:

📊 Why 92% of owners would trade cash flow for a better experience
🏠 How maintenance friction creates kitchen table arguments and churn risk
🤝 Why AI gives teams bandwidth to protect owner trust
🏆 What the PM.com rankings reveal about perception versus performance
⚙️ How maintenance AI is shifting from task support to owning more of the work

🎧 Listen now to understand why owner retention is no longer defended by NOI alone, and what the latest PM reports reveal about the future of maintenance operations.

🌟 Stay Connected with Us:
🎙️ Connect with Pablo Gonzalez on LinkedIn
📬Subscribe to Vendoroo's Weekly Newsletter
💼 Follow Vendoroo on LinkedIn
🌐 Visit Vendoroo's Website

Chapters:

00:00 – Two Industry Reports Point To One Misconception
01:45 – The Gap Between PM Output And Owner Expectations
03:20 – Why Owners Trade Cash Flow For Fewer Headaches
04:14 – The Headache That Pushed An Investor Out Of Real Estate
06:12 – One Maintenance Bill Can Break Owner Trust
07:30 – Kitchen Table Arguments Create Churn Risk
08:12 – Why Net Operating Income Will Not Prevent Churn
09:16 – AI Bandwidth Protects The Owner Relationship
10:58 – Performance Outcomes Versus Market Perception
11:41 – The Architectural Shift From Coordination To Execution
14:14 – Putting Out Embers Before Resident Issues Escalate
15:55 – Are You Playing On Hard Mode With Legacy Software? (The Threat)
16:48 – Playing The New Maintenance Game (The Opportunity)