The Journey Begins with Ray Hespen

Ray Hespen, CEO of Property Meld, doesn’t follow the typical path of a tech founder. His journey into property maintenance and innovation started as a mining engineer.“I barely passed engineering school with a 2.9 GPA,” Hespen quips during our conversation. His early days in mining taught him the value of operational efficiency. When the 2008 financial crisis hit, Ray took on roles that required him to do more with less. This experience shaped his passion for optimization.During a frustrating experience as a renter, Ray’s co-founder asked him a pivotal question: “Is it normal for maintenance to be this bad?” Intrigued, Ray analyzed the workflows of 25 property management companies. He discovered outdated systems and endless opportunities for automation. This realization planted the seed for Property Meld, which he founded in 2014 with a mission to simplify and improve property maintenance.Today, Property Meld leads the way in automating maintenance processes, from communication to scheduling. But Ray’s path wasn’t without challenges.

The Challenges of Maintenance and Selling Solutions

Property maintenance often takes a backseat in the property management industry. Many see it as a cost center, ranking low in priority until something goes wrong.“When we started pitching, property managers didn’t see maintenance as a pain point,” Hespen recalls. “They’d say, ‘We’ve got property management software, we’re fine.’” This mindset ignored the hidden costs of inefficiency: high staff turnover, negative resident experiences, and reduced NOI (Net Operating Income).Maintenance teams operated in constant firefighting mode. Follow-ups were inconsistent, communication was fragmented, and the sheer volume of tasks overwhelmed staff. “Firefighting is expensive. And it’s a system designed to fail,” Hespen explains.This operational chaos stressed maintenance coordinators, who needed soft skills for resident communication but also logistical expertise—a nearly impossible combination. The result? High turnover and unhappy residents. Maintenance professionals found themselves in an unwinnable game, simply trying to minimize losses.Meanwhile, selling solutions to these problems required more than a sales pitch. Convincing property managers to prioritize maintenance demanded a complete shift in mindset.

The Hell Yes Mindset

Ray Hespen’s breakthrough came with a powerful shift: a great example of “Getting to Hell Yes!”. This philosophy goes beyond traditional selling. It centers on understanding the customer’s pain points and helping them see the urgency of solving them.“We judge our sales team on whether the customer has meaningful pain that we know we can solve,” Hespen says. “If they do, that’s a deal. If not, we walk away.”This approach stems from Zig Ziglar’s principles of ethical selling: identify the customer’s problem and help them recognize its importance. Hespen elaborates, “I already know their problems because I’ve talked to thousands of operators. But the key is, do they know their problems?”The process stays intentionally question-driven. Instead of pitching a product, Property Meld’s team uncovers the root causes of inefficiency. For example, Hespen might ask, “Why are your residents unhappy?” or “What’s causing your staff turnover?” These questions often lead to moments of clarity for potential customers.“The best feeling in the world is helping someone realize they don’t have to deal with these problems anymore,” Hespen shares. “There’s visible relief on their face. That’s when you know you’ve hit ‘Hell Yes.’”

Building a Better Sales and Maintenance Ecosystem

Prioritizing maintenance has delivered tangible results for Property Meld and its clients. Here’s how Hespen and his team turned the tide:

Automating Processes

Property Meld streamlines the maintenance process by automating follow-ups and communication. For every thousand rental units, there are roughly 400 individual maintenance instances requiring multiple follow-ups. Expecting humans to manage this manually guarantees failure.Automation reduces errors and lets staff focus on what truly matters: building relationships with residents and vendors. The result? Higher efficiency and happier teams.

Using AI for Smarter Maintenance

A game-changer for Property Meld came with its acquisition of Mezzo, an AI-driven solution featuring Max, a virtual assistant. Max helps residents troubleshoot issues or gives technicians all the necessary information for a single-trip resolution.“It’s like having a patient, empathetic technician sitting on your shoulder,” Hespen jokes. Max eliminates redundant work orders and equips technicians to handle problems efficiently. This proactive approach cuts costs and improves resident satisfaction.

Changing Maintenance Culture

Beyond the technology, Hespen drives a cultural shift in how maintenance is viewed. Once a reactive function, maintenance now drives NOI and tenant retention. This shift leads to smarter hiring practices, focusing on soft skills for maintenance coordinators and better tools to support them.“The goal is to create a system where maintenance teams thrive,” Hespen says. “When you empower them with the right tools and training, everyone benefits—from the residents to the property owners.”

Key Takeaways for Getting to Hell Yes!

Ray Hespen’s journey offers valuable lessons for anyone aiming to excel in sales or operations. Here are three takeaways:

1. Empathy and Listening Are Key: Truly understanding your customer’s pain points requires active listening and empathy. Ask the right questions to help them see the importance of solving their problems.
2. Focus on the Right Fit: Don’t waste time chasing deals with customers who don’t align with your solution. Spend your energy on those who genuinely need and value what you offer.
3. Sell Solutions, Not Products: Frame your offering as a resolution to specific problems. Show how your solution creates tangible value—whether it saves time, reduces costs, or improves satisfaction.

The Power of Persistence and Empathy

Ray Hespen’s story proves the power of persistence, empathy, and innovation. By solving meaningful problems and building trust with customers, Property Meld has transformed its business and the property management industry.Getting to Hell Yes isn’t just about closing a deal. It’s about creating moments of clarity and relief for your customers, helping them overcome challenges they once thought were insurmountable. When you see that look of relief on their face, you’ll know you’ve done your job.So, what’s your next ‘Hell Yes’ opportunity? As Ray Hespen says, it starts with understanding the problem and making it go away.

Listen to the “Getting to Hell Yes!” podcast on apple or spotify here:

https://open.spotify.com/show/4TY87ToVuLK7eqkZZvZA5T

https://podcasts.apple.com/gm/podcast/getting-to-hell-yes/id1772602174