Scaling Property Management with Systems & Tech with Sean Miller CRO of Lessen
In this episode of Uncontested Investing, we sit down with Sean Miller, Chief Revenue Officer at Lessen, to explore how technology is reshaping property management. From single-family rentals to multifamily and commercial portfolios, Sean shares how Lessen streamlines maintenance operations, uses AI and IoT to anticipate repairs, and helps investors scale more efficiently without losing control of their assets.
Whether you’re a landlord managing two homes or a professional operator with hundreds of units, this conversation unpacks how to combine local expertise, operational systems, and smart technology to stay ahead in today’s evolving real estate landscape.
Key Talking Points of the Episode
00:00 Introduction 01:00 How Sean got into real estate investing 02:06 The common characteristics of successful leaders 03:09 Building Lessen and scaling to 3.5M+ work orders 04:37 Property management as a tech-enabled service 06:30 Sean’s Deal Breaker/Deal Maker: the most pivotal moment in his career 08:02 When should a real estate investor hire a property manager? 10:22 Leveraging tech in property management with Lessen 11:36 Core features every scalable property management system needs 13:49 IoT use cases: From smart fridges to HVAC monitoring 16:23 The resident experience & retention strategies 17:40 What is IoT? 19:03 Managing turnover timelines & vendor reliability 20:46 Lessen’s use of AI for task routing & QC optimization 22:19 What’s next for Lessen and how to partner with them
Quotables
“Tech is powerful, but it has to solve a real need. For us, it’s about making operations more efficient and predictable.”
“You miss 100% of the shots you don’t take—and if you’re afraid of mistakes, you’ll never innovate.”
“Cost is what you pay. Value is what you get. And faster turns mean more value, even if the price is higher.”
Links:
Lessen
RCN Capital
https://www.rcncapital.com/podcast
https://www.instagram.com/rcn_capital/
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