Getting to Hell Yes! with Sean Landsberg from AppWork

There’s something about Sean’s energy that hits you before he even finishes his first sentence. He is refreshingly direct, it’s captivating. Every time I talk to him, I walk away with ideas and a sharper sense of where our industry is heading. Sean is rebuilding how property management sees maintenance.

I started our conversation the way I usually do: by asking “why in the world would anyone start a property maintenance software company.” He just laughed.

“I realized the hard way that property management and startups are two completely different worlds,” Sean told me.

We both laughed (and maybe shed a tear! 😂).  Every founder I’ve met has that same moment – the one where you discover you’ve signed up to unlearn everything you thought you knew. But Sean’s advantage was unique: he’d lived the pain firsthand. He wasn’t guessing at what property managers needed; he’d been one. That’s why his product didn’t start with code. It started with a clipboard and a problem.

He knew the tech had to serve the people actually doing the work, not the ones sitting in conference rooms talking about it. That’s something I’ve learned too: empathy is the best product manager in the room.

“The biggest problem we have isn’t selling our product,” Sean said. “It’s convincing people they even have a problem.”

We live this together. Even though ALL the data points to it as the most important part of the revenue experience. Companies are willing to spend thousands on new marketing campaigns while their maintenance teams drown in work orders. It’s not willful ignorance; it’s just familiarity. Decision-makers solve the problems they understand.

I told Sean that I’ve been guilty of this too. Focusing on optics when the real leak is under the floorboards. He nodded. The two of us agreed: most properties don’t have a marketing problem; they have a maintenance problem that’s being disguised as a marketing problem.

“Maintenance has a direct impact on every KPI in property management,” he said. “If your AC’s broken in 103-degree heat, why are you paying rent?”

BAM! I’ve spent my whole career in and around maintenance and yet I still catch myself forgetting how deeply it touches everything – occupancy, retention, delinquency, morale. It’s the one department everyone relies on and the one that gets thanked the least.

Sean’s passion for the techs are the real first responders of property management. It reminded me of why I do what I do. These are the people keeping residents comfortable, safe, and loyal. They’re also the people burning out the fastest.

“We built a gamification program so maintenance teams can actually get recognized for their work,” he explained.

Now, that was something I didn’t expect. Digital badges, shoutouts, company-wide recognition, it sounded simple but the psychology behind it is powerful. Maintenance is a constant stream of complaints. Creating moments to celebrate small wins keeps morale alive.

I told him how I’d seen too many teams lose their best techs because no one ever said, “good job.” Sean laughed knowingly. “Exactly,” he said. “If you don’t recognize the right people, you start losing them.”

Hearing him talk about this reminded me that technology can be human too. When it celebrates people, it becomes culture.

“People like solving the problems they’re comfortable with,” Sean said near the end. “That’s why we keep buying CRMs instead of fixing maintenance.”

That truth is hard to hear, hard to accept. It’s easier to polish the front door than fix the plumbing but as Sean put it, the only amenity every single resident uses is maintenance. You can’t lease your way out of a broken water heater.

What I learned from Sean is that maintenance isn’t just a cost center, it’s a trust center. When it runs well, everything else gets easier: occupancy, reputation, employee retention. When it fails, the business bleeds quietly.

From my side of the table, here’s what I took away and what I’m still asking myself:

• How often are we mistaking visibility for value? Just because we see leasing doesn’t mean it matters more than maintenance.
  
• Are we building products that empower the people doing the work or just reporting on their output?
  
• What if our goal wasn’t just to “digitize” maintenance but to dignify it?
  
• How do we make our recognition systems louder than our complaints?

Sean reminded me that getting to “Hell Yes!” starts with solving the problems that matter most even if they’re not the ones we’re used to solving. Maintenance is the heartbeat of this business. Ignore it, and the rest stops working.