Article 4 of 4 — The NAA Series

A Different Path to the Future of Leasing.

By Steve Bonaventure · Founder & CEO, Pineapple

This is my last article before NAA, and I want to use it to do something different. I'm not going to talk about Pineapple's product. I'm not going to talk about kiosks or chatbots or concession strategies. I want to talk about where this industry is going — and offer a different map for how to get there.

Because right now, most operators are being told there are only two options.

Option one: stay the course with traditional leasing. Full onsite teams, office hours, the model we've all known for decades. Increasingly expensive, increasingly hard to staff, and increasingly out of step with how renters actually behave.

Option two: go all-in on AI. Automate everything. Replace leasing agents with chatbots. Cut headcount. Let the technology handle it.

I've spent the last few weeks laying out why option two isn't working the way it was promised. But I'm not here to argue for option one either. Traditional leasing in its current form is not sustainable.

What I want to lay out is option three. A path that gets you to fewer people on site, lower operating costs, and a better renter experience — without gutting the human element that actually closes leases.

The Destination

Let me describe where I think the best-run properties will be in two to three years. Not ten. Not five. This isn't a moonshot. This is an achievable near-term future.

Where This Goes

One person on site. That's it. One person whose primary job is not leasing — it's resident support. Taking care of the people who already live there. Being the face of the community.

Leasing support lives offsite. A dedicated concierge — a real person, not an AI — who knows your property, knows your available inventory, and handles the entire prospect journey from first inquiry through signed lease.

Technology handles the infrastructure. Scheduling. Access control. Navigation. Data. The things that technology is actually good at.

This isn't science fiction. This is already working at properties on our platform today. The question is how you get there from where you are now without blowing up your operations in the process.

The Migration

Here's what I'd tell any operator who's looking at their leasing costs, looking at their vacancy rates, and looking at the gap between what they're spending and what they're getting.

Don't rip and replace. Migrate.

1

Start with self-touring.

Not the model-tour version — real self-touring, where prospects can access actual available units on their own schedule. This extends your leasing hours without adding staff, and starts training your organization to operate differently.

2

Add offsite leasing support.

Keep your onsite team exactly as it is, but layer in a concierge who handles the pre-tour and post-tour experience. Don't take anything away — add capability. Let your onsite team see what it feels like when prospects arrive warmer, more informed, and further along in the decision process.

3

Then — and only then — right-size.

Once the offsite support is handling the top of the funnel reliably, you'll see that your onsite team's highest-value work is closing and resident care. The rebalancing will happen naturally as you see where the value is actually being created.

The end state is one onsite person focused on residents, a dedicated offsite leasing partner, and technology handling the plumbing. You get there gradually, and at every step, the renter experience gets better, not worse.

Why This Protects Your Margins

The concession wars are destroying margins. Properties in competitive markets are giving away months of free rent to fill units. That's not a marketing strategy — that's a sign that the leasing process itself isn't working.

The hybrid model protects margins differently. You pay for leasing support that's tied to outcomes — tours completed, leases influenced, problems solved. You're not carrying the fixed cost of a full leasing team during slow months, and you're not leaving money on the table during peak months because your chatbot can't close.

When a renter has a great experience — when someone helped them find the building, walked them through the process, and followed up like they mattered — the need for a massive concession drops. You're not buying their attention anymore. You've earned it.

The Larger Portfolio Play

For operators managing larger portfolios, there's an additional opportunity that most people aren't thinking about yet.

Imagine assigning a dedicated concierge to your portfolio — not just a property, but the full group. Someone who knows every community you operate, what's available across all of them, and can match a renter's needs to the right unit at the right property.

A prospect tours a one-bedroom at your downtown property and loves the community but needs more space? Your concierge already knows you have two-bedrooms opening up at your suburban property ten minutes away. That's not a lost lead — it's an internal transfer that keeps the renter in your portfolio.

This kind of cross-property leasing doesn't happen in a world of isolated AI chatbots, each one only aware of its own property.

It requires a person who sees the full picture and is empowered to act on it.

What I'm Not Saying

I want to be clear: I'm not anti-AI. I'm not anti-technology. I've spent my entire career building technology for this industry.

What I am against is the idea that technology alone can replace the human judgment, empathy, and adaptability that closes leases and retains residents. The last few years have been a real-time experiment in what happens when you try, and the results are in.

The future of leasing involves AI. It involves automation. It involves fewer people on site. I believe all of that. But it also involves humans — in the right places, doing the right work, available when the renter needs them. That's not a step backward. It's the step the industry skipped.

If any of this resonates — if you're an operator who's been feeling the tension between the pressure to automate and the knowledge that your renters deserve better — come find us at NAA. I'm not going to pitch you from a booth. I want to hear what you're seeing in your markets. What's working, what's not, and what keeps you up at night.

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Steve Bonaventure is a three-time proptech founder with 20 years in multifamily. He founded Apartment Guardian, Checkpoint ID, and now Pineapple. Headquartered outside Boston, MA.

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