Ilya Drozdov, Co-Founder & CEO of Dwelly. Scaling AI-Powered Property Management Rollup
One of the most interesting themes emerging in the serial acquisition ecosystem today is the rise of AI-enabled roll-up platforms.
In this live session, we move beyond theory and explore what happens when AI is embedded directly into day-to-day operations — from tenant screening and maintenance coordination to portfolio pricing and integration workflows.
Join Ilya Drozdov— Co-Founder & CEO of Dwelly — for a practical discussion on how AI-native operating models can transform fragmented service industries such as property management.
Before launching Dwelly in the UK, Ilya built and exited a 10,000-unit residential management platform in Moscow and previously served as one of Uber’s youngest global General Managers, overseeing multi-city operations at scale.
At Dwelly, he is now applying AI agents and automation to fundamentally rethink how rental portfolios are operated and consolidated.
We’ll cover:
• Where AI is creating measurable operational impact inside roll-up platforms
• What integration looks like in the first 90 days after acquiring a property manager
• Whether AI-enablement creates durable competitive advantage — or simply becomes table stakes
• How aspiring roll-up entrepreneurs should think about building an AI roadmap from day one
Who is Dwelly?
Dwelly is an AI-powered property management platform focused on acquiring and scaling residential rental portfolios.
Rather than layering software onto traditional workflows, Dwelly is building infrastructure designed specifically for AI agents — enabling automation across compliance, maintenance coordination, tenant communication, and pricing optimization.
Who Should Join
This session is designed for:
• Private equity investors and independent sponsors
• Serial acquisition entrepreneurs and holdco founders
• Operators in property management or other fragmented service industries
• Anyone interested in how AI can drive real operational leverage in roll-up strategies
If you want to understand how AI can move from pitch-deck narrative to operational reality inside acquired businesses, this session will provide a practical playbook.