The Leasing Machine Wins Fast—But Retention Builds Value

Multifamily operators have mastered leasing. They’ve optimized websites, deployed AI chatbots, and trained high-performing leasing teams—all to lock in that confident “hell yes” from prospective residents.

But what happens after the lease is signed?

Jude Chiy, CEO and founder of Flamingo, asked that question—and built a company around the answer. Flamingo began by managing resident events, but Jude quickly realized that events alone couldn’t plug the holes in the resident journey.

“Leasing is sophisticated,” Jude said. “But retention? Most companies still treat it like an afterthought.”

Instead of dismissing the problem, Jude leaned in. He saw what others missed: leaks. Small missteps—miscommunications, unmet expectations, slow responses—that quietly drive residents out the door.

Residents Don’t Leave Over One Thing—They Leave Over Everything

The first leak starts with the lease. A prospect signs for $2,000 a month, then finds out there are $500 in hidden fees. Move-in day arrives, but the leasing agent is unavailable. The unit isn’t clean. The welcome email never comes.

Each moment erodes trust.

“We’re hardwired to avoid pain,” Jude explained. “And when something hurts—even a little—we start looking for patterns of failure.”

Residents don’t just compare apartments. They compare every interaction to Uber, Amazon, and Netflix. If they can’t get fast answers or seamless experiences, they feel like the property doesn’t care.

“Once trust starts falling, every issue feels bigger than it is,” Jude said. “A late maintenance ticket becomes proof that no one’s listening.”

And when lease renewal time comes, that stack of disappointments outweighs convenience—and they leave.

Turning Engagement into Retention Intelligence

Instead of adding more events or discounts, Jude did something different—he built Flamingo into a central hub for the entire resident journey.

“We turned events into data, data into insight, and insight into action,” Jude said.

What started as a simple RSVP tool became an intelligent app that tracks every interaction—from surveys and service requests to amenity usage and peer-to-peer messaging.

“We don’t guess,” he added. “We know which residents are likely to renew based on what they do, what they say, and what they don’t use.”

If a resident never touches the gym, Flamingo flags it. If they frequently post frustrations on the bulletin board, it alerts the team. Every data point contributes to a living retention score.

“Most companies have the data—they just don’t act on it,” Jude said. “We make it visible and actionable.”

Finding the Right Buyer

Not everyone’s ready for that kind of visibility. And that’s exactly the point.

Jude doesn’t try to sell to everyone. He looks for what he calls philosophical alignment—buyers who already know retention matters and want to fix it.

“The best customers feel the pain already,” he said. “They’re not window shopping. They’re ready to get serious.”

Flamingo typically works with owners or revenue managers, not site-level staff. These roles tie retention directly to bottom-line metrics like NOI and asset value.

“Every lost resident costs $3,000–$5,000 to replace,” Jude explained. “Improving retention by just 10% can add hundreds of thousands in value.”

Owners see the return immediately. They’re not just chasing leads—they’re protecting investments.

Retention Isn’t a Role—It’s a Culture

Flamingo doesn’t just plug into a team—it reshapes how teams think.

“We don’t just deliver software,” Jude said. “We drive a mindset shift.”

High-performing clients rethink how they onboard, communicate, resolve issues, and celebrate wins. They create accountability across departments—not just in leasing.

“If your building has a VP of leasing but no VP of retention, you’ve already shown your priorities,” Jude said. “Retention needs a seat at the table.”

Jude even shared a story about one client—a property owner—who logged into Flamingo on a weekend to personally respond to a resident ticket. That level of engagement isn’t just rare—it’s powerful.

“That’s how you create trust,” Jude said. “By showing residents that someone cares, even when no one’s watching.”

Throwing Parties Won’t Fix the Problem

When residents complain, some teams rush to throw another pizza party. But Jude sees that as a missed opportunity.

“Events are the cherry on top—not the cake,” he said. “If you’ve got 200 unresolved tickets, a party won’t solve anything.”

Instead of masking pain with gifts or gimmicks, Flamingo urges clients to address root causes.

“Fix what’s broken first,” Jude said. “Then celebrate.”

Every response, every fix, every piece of clear communication contributes to retention. Residents don’t just want fun—they want consistency, clarity, and respect.

3 Takeaways to Get to Hell Yes in Retention

1. Sell to Alignment, Not Just Interest

Look for buyers who already believe in the value of retention and have the power to act on it. Don’t chase everyone—chase the right ones.

2. Make Retention a Company Strategy

Stop treating retention like a site-level side hustle. Build it into how the entire organization operates—from the front line to the C-suite.

3. Lead with Outcomes

Focus on results, not features. Align every conversation around a single outcome—like 75% retention—and let that guide the journey.

Practical Rebels Win the Long Game

Jude doesn’t sell to skeptics. He partners with practical rebels—those rare leaders who believe retention can and should be radically better.

“Flamingo isn’t for everyone,” he said. “But for the rebels who believe 75% retention is not just possible—but necessary, we’re ready.”

Improving retention isn’t complicated. It just requires discipline, data, and a real commitment to people.

“This is the four-minute mile,” Jude said. “Once one person does it, everyone else will follow.”

Ready to Get to Hell Yes?

If you’re tired of throwing money at leasing while watching current residents walk out the door, it’s time to shift the conversation.

Start with trust. Start with insight. Start with Flamingo.

• 🔗 Visit getflamingo.com
• 🎧 Listen to the Apartment Rebels podcast
• 💬 Connect with Jude Chiy on LinkedIn