Top STR Voices Every Professional Property Manager Should Learn From

The short-term rental industry isn’t just growing—it’s maturing. What started as a fragmented, host-led ecosystem is now moving toward consolidation, institutional investment, and operational complexity at scale. Regulations are tightening, tech stacks are becoming non-negotiable, and profitability—not just growth—is back in focus.

For professional property managers (100+ units), the game is fundamentally different. It’s no longer about just acquiring more units—it’s about building resilient systems, navigating market shifts, and making high-stakes strategic decisions. The voices below are shaping how that playbook is being written.

Simon Lehmann

Few people have had a front-row seat to the STR industry's evolution quite like Simon. With over two decades across travel, tech, and vacation rentals, his perspective is both deeply strategic and refreshingly current. As the founder of AJL Atelier and former leader at companies like Vacasa Europe and PhocusWright, he sits at the intersection of operators, investors, and technology.

Through the STR Unlocked podcast, he regularly convenes founders and industry leaders shaping the future of hospitality—bringing large PMs closer to the conversations driving change. What makes his voice stand out is his ability to connect macro trends—regulation, consolidation, AI—to real business decisions. His insights consistently challenge leaders to think beyond short-term wins and build businesses designed to last.

Steve Schwab

Steve Schwab represents what disciplined, long-term scaling in STR actually looks like. As the founder of Casago, he built a business centered on sustainable growth, local expertise, strong owner relationships, and operational consistency—not aggressive expansion at all costs.

In an industry long obsessed with rapid growth, his focus on profitability and resilience feels both countercultural and necessary. For large PMs navigating today's volatility, his perspective is a steady reminder that durable businesses are built on fundamentals, not just scale.

Jamie Lane

Jamie Lane brings a data-first lens to understanding the STR landscape at scale. As Chief Economist at AirDNA, his insights are grounded in market-wide trends — occupancy shifts, pricing dynamics, supply growth, and demand patterns across regions. His analysis helps large PMs zoom out and see the bigger picture beyond their own portfolio performance.

What makes his perspective particularly valuable is how he translates complex data into clear, actionable insights. Whether it's understanding shifts in travel behavior or anticipating seasonal fluctuations, his work helps operators make smarter, more informed decisions.

Tim Rosolio

Tim Rosolio offers a platform-level perspective that few others can. With experience spanning Vrbo and Expedia Group, he brings rare insight into how large operators fit into the broader ecosystem of distribution, demand, and platform strategy — bridging the gap between what platforms prioritize and how property managers can align with those dynamics.

As the industry continues to professionalise, that alignment becomes increasingly important. For large PMs, his perspective provides a clearer understanding of how to navigate — and leverage — the platforms that drive a significant share of their business.

Graham Donoghue

Graham Donoghue operates at the helm of one of the largest vacation rental businesses in Europe, giving him a unique vantage point on scaling in a highly competitive market. As CEO of Sykes Holiday Cottages, he's focused on balancing growth with customer experience, brand strength, and operational efficiency.

His approach reflects the realities of running a large, established organization — where decisions are not just about expansion, but about maintaining quality at scale. For large PMs, it's a case study in how to grow without diluting what makes the business work in the first place.

Thibault Masson

Thibault Masson has carved out a distinct voice in the STR space by focusing on one of the most important levers at scale: distribution. He consistently challenges operators to rethink overreliance on OTAs in favour of stronger direct booking channels and a more intentional channel mix.

What sets him apart is his ability to simplify complex distribution strategies into practical, actionable frameworks—from optimizing channel performance to improving direct conversion. We're also grateful to have his perspective as part of the broader PriceLabs ecosystem, where his insights continue to shape smarter conversations around growth and distribution. For large PMs, his work turns distribution from a dependency into a strategic advantage.

Jessica Gillingham

Jessica Gillingham operates at the intersection of marketing, brand, and industry narrative. As the founder of Abode Worldwide, she works closely with STR operators, hospitality brands, and tech companies on positioning and growth strategy.

Her perspective focuses on how STR companies show up—not just to guests, but to investors, regulators, and the broader market.At scale, reputation becomes infrastructure. Her insights are a reminder that how you're perceived—by guests, investors, and regulators alike—shapes the runway you have to grow.

Sally Henry

Sally Henry brings a sharp focus on what actually holds large STR businesses together—people, process, and leadership. Drawing from senior roles across hospitality and vacation rentals, including VP at Key Data, she emphasizes building high-performing teams and operational clarity as portfolios scale.

Her perspective consistently returns to the fundamentals: culture, alignment, and disciplined execution. The message is consistent: growth without the right people and processes underneath it is fragile. At scale, success is driven less by adding units and more by running better operations.

Dustin Abney

Dustin Abney arrives at Portoro with a résumé few STR operators can match — VP of Homes at AvantStay, Vice President at Zillow Group, and co-founder of D. Alexander before building Portoro into a premium, tech-enabled property management company operating across top leisure markets in the US.

What runs through all of it is a focus on execution at scale. He's vocal about the things large operators tend to underestimate — team alignment, operational accountability, and the compounding cost of small inefficiencies across a big portfolio. For large PMs, his insights are grounded in having actually built and stress-tested these systems, not just observed them.

At scale, the STR business becomes less about individual wins and more about building systems that hold under pressure. The operators and thinkers above reflect that shift—prioritizing structure, strategy, and long-term positioning over quick growth hacks. If you're managing a large portfolio, these are the voices helping define what sustainable scale actually looks like.

And if you're earlier in your journey—or still building toward that level—our companion piece on scaling property managers is where you'll find more hands-on, ground-level insights. The operators featured there are figuring things out in real time—and the lessons they share are often the ones that matter most before scale makes everything harder to change.