In a world where real estate tech often overwhelms and underdelivers, Justin Dilley flips the sales script. He doesn’t just sell software. He guides people through complexity, clears up confusion, and makes it easier for them to say, “Hell yes!”This is the story of how one multifamily leader uses empathy, insight, and deep customer understanding to move people past indecision and toward confident choices. And what he teaches about modern selling is worth every word.
From Improv to Proptech
Justin Dilley doesn’t start out in software. He begins on the stage, with a background in teaching and performance. That experience—reading people, listening, telling stories—becomes his greatest sales asset.He tries out real estate leasing during grad school, pounding the pavement and learning the business from the ground up. Eventually, he joins MRI Software, a global real estate tech company that serves everything from commercial buildings to multifamily properties. Today, Justin leads strategic accounts and writes Multifamily Weekly, a punchy, insight-packed newsletter that industry insiders love.“I didn’t plan for a career in proptech,” Justin says. “But once I got in, I realized how powerful software could be for solving real-world problems.”But Justin isn’t just a relationship manager or sales pro. He advocates. He advises. He cares deeply about helping operators make better choices in a noisy marketplace.And that’s where the story really begins.The Problem with Selling to Everyone
MRI Software has been around for over 50 years. Some see that as a badge of trust. Others remember clunky systems from years past.“You knew MRI in 1970 or 1989 or 1999,” Justin says. “But what is MRI today?”The challenge isn’t that MRI lacks value. The challenge is that buyers can’t always see it through the clutter. Multifamily tech stacks overflow with overlapping, underperforming tools. Operators hesitate to rip and replace unless they’re sure it matters.“People don’t change because of price,” Justin says. “They change because of how a problem makes them feel—the anxiety, the friction, the frustration. That’s where the energy for change comes from.”Understanding those feelings takes time. It takes listening. It takes trust.“Every client I work with has history with other platforms,” he says. “So I don’t walk in assuming anything. I walk in asking everything.”That’s why Justin doesn’t rush the sale. He spots patterns, starts conversations, and plays the long game—especially in a fragmented industry like multifamily.When Selling Becomes Serving
Justin’s most powerful strategy comes from improv: “Yes, and.”In improv, you never block the story. You say yes to what your partner gives you—and then build on it. Justin uses the same mindset in sales.“When someone says no, I don’t fight it,” he says. “I accept it. Then I ask, what next? I keep the door open. I look for another way to help.”He doesn’t manipulate. He collaborates. He respects his clients. He avoids one-size-fits-all pitches and instead digs deep to understand what’s really happening.Is the client navigating a merger? Managing new regulations? Struggling with resident renewals? Justin tailors each conversation to that context.“I always ask, what’s changed recently in your world?” he says. “That usually uncovers more than any sales demo ever could.”He watches for external events that create urgency—legal shifts, economic changes, new tech trends. These are the moments when people open up to change. When they do, Justin helps them connect the dots.“Data without context doesn’t mean much,” he says. “People don’t just want dashboards. They want insights that move them forward.”He positions MRI as a flexible ecosystem, not a rigid system. Clients don’t need to replace everything—they can plug in what they need. That’s a major relief in a world of bloated stacks.“That’s when you hear it—the real ‘hell yes,’” Justin says. “It’s not loud. It’s confident.”That’s how Justin helps clients go from skeptical to sold.Team Everyone, for the Right Few
Justin doesn’t try to sell to everyone. He focuses on the right people, at the right time. He doesn’t push product. He solves for vision.“It’s not about being team blue or red or orange,” he says. “It’s about being team everyone—for the accounts I serve.”That’s account-based selling at its best. Justin studies his clients. He reads what they write, tracks their markets, notices changes in leadership and even details like murals on their buildings. Then he shows up prepared.“Most of the work happens before the meeting,” he says. “That’s where the advantage lives.”That help might include a new data tool, a security feature, or a reporting solution—but it always connects to what the client wants to build.“If someone wants to go this way,” he asks, “how can I help them do it better?”This approach isn’t just about retention. It’s about renewal—not only of leases, but of trust and shared purpose. As multifamily leans toward hospitality-style branding and consistency, that kind of relationship-building becomes a superpower.“You can’t be everything to everybody,” Justin says. “But you can be everything to the right few.”Three Takeaways on “Getting to Hell Yes!”
1. Embrace the "Yes, and" MindsetA "no" doesn’t end the story. It starts a new scene. Great sellers don’t resist rejection. They respond with curiosity, empathy, and follow-up. Accept the no. Then offer a way forward.2. Use External Events as CatalystsPeople change when outside forces push them to. Mergers, legal shifts, and economic pressure all create urgency. Spot these signals early and speak to them.3. Know Your Customer Better Than Your ProductYou don’t need to know every feature. You need to know your client. What stresses them? What inspires them? What do they value? Understand their goals and your solution will click into place.Say Yes to the Long Game
Sales isn’t about clever tricks or perfect pitches. It’s about patience, empathy, and showing up to help.“I’m not chasing wins,” Justin says. “I’m chasing clarity.”Justin Dilley doesn’t chase quick wins. He builds long-term partnerships. And when clients finally see the value, connect the dots, and commit to change, they say it with confidence:“Hell yes.”Our mission is to simplify the homeowners & home builders customer experience. Let Iris do the work.
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