
Robert Dell'Osso
CEO, Broker-in-Charge, and founder of MasterKey Property Management in the Raleigh/Cary, NC Triangle area, and active NARPM leader (MPM, RMP designations).
3
APPEARANCES
2
PODCASTS
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Oct 21, 2026
Conference ROI: Why Walking In With Three Problems Beats Walking Out With Fifteen
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Pete NeubigHOST
Like, how, you know, the mindset going in and then the mindset coming out of the conference.

Robert Dell’OssoGUEST
Yeah, and, uh, I have been going to conferences for a while, and I was actually fortunate enough to speak on something similar a couple weeks ago at the AppFolio Future Conference, so it's perfect timing.

Robert Dell’OssoGUEST
You know, try to brainstorm and identify what kind of bottlenecks do you have in your company, or things that are just repetitive administrative type things that you do over and over but they take up a lot of your time when you add them all up.

Robert Dell’OssoGUEST
Like, how can I solve these, these, uh, operational constraints or bottlenecks I have? Instead of just going in and learning about every vendor solution, I, I, you know, pick my own topics and then I narrow it down and talk to those vendors and see what they have to offer and see if I can come up with, uh, solutions to my problems, right? And maybe that solution is signing up with a vendor.

Robert Dell’OssoGUEST
Maybe that solution is creating some sort of a new process or automation, or utilizing AI even.
6 MINS LATER
Ep 145 | If AI Owns the Work Order, What Does the PM Own?
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David NormandGUEST
That's when we start moving to tenant sentiment, vendor performance, human interactions, calling people in real time.

Robert Dell'OssoGUEST
Like you mentioned, we're control freaks, right? I know when I have less doors somebody had submitted a maintenance request in their portal and popped in my email and we all live on our phones i'd see it i want to jump in there no matter what time of day and it really had to like mentally change my mindset to let it do its job the whole idea is to offload the heavy lift from you and the stress and let it do what it's supposed to yes and you kind of have to force yourself it will take you
Ep 137 | Is Your PMC Ready for the New Maintenance Standard?
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Robert Dell’OssoGUEST
then you're paying for technology and not getting any of the efficiencies, right? You really need to make sure when you sign up with a vendor, you're not just looking at the cost, but does it solve an operational constraint you have? Will it help you run your business more efficient? That's a hard decision to make, right? Because you're affecting humans' lives, right? But at the end of the day, you also...

Robert Dell’OssoGUEST
have an obligation to do what's best for your business to try to make it successful.

Robert Dell’OssoGUEST
We do have maintenance coordinators on staff because a human element is needed as an escalation process.