Keynotes by Steve Schwab

Booking.com’s Betsy Steckler on Experimentation, AI, and What Travelers Really Want

Host Steve Schwab interviews Betsy Steckler, Regional Director Partner Services of North America at Booking.com, about how the company uses data-driven experimentation and iteration—running about 1,000 experiments a day—to optimize traveler experiences and partner conversion rather than relying on opinions or flashy design. Betsy explains why Booking sometimes “zigs” when competitors “zag,” and shares lessons from launching and shutting down Villas.com, framed as a “fail fast” learning that reinforced travelers’ desire to compare all accommodation types in one place and helped shape the Connected Trip vision. She outlines three traveler truths from Booking’s annual survey of about 30,000 people: accountability, value for money, and authenticity, and discusses AI’s role in speeding decisions while keeping final booking decisions human. Betsy advises property managers to focus on differentiation, content, reviews, cancellations, and traveler mix, emphasizing partnership and collaboration with Booking.com.

00:00 Welcome and Guest Intro
00:27 Betsy Background and Role
01:36 AI and Staying Relevant
03:07 Competition and Data Culture
05:39 A Thousand Experiments Daily
08:36 Why Booking Zigz
14:01 Villas.com Lessons Learned
17:10 Fail Fast Culture
21:01 Onboarding for Experimentation
25:06 Connected Trip Expansion
28:13 Three Traveler Truths
30:44 AI Trust and Human Choice
33:37 Advice for Property Managers
38:50 Signals Reviews and Cancellations
41:42 Using Competition to Grow
44:44 Ranking Risks and Reviews
45:53 Future Partnership and Wrap Up

Mike Mears on Extend Team’s Shared Services: Blending AI and Human Support for Vacation Rentals

Host Steve Schwab interviews Mike Mears, Extend Team’s global head of revenue, about his shift from OTAs and AI tools into staffing and why he prioritizes a people-first approach. Mears describes building an AI-driven vacation rental education library for newcomers and explains how Extend Team is evolving from traditional staffing (30–45 day hiring) to a shared services, plug-and-play model combining trained human support with AI handling routine guest inquiries for faster response times and better reviews. He argues AI can cover up to 80% of tasks but struggles with high-empathy, high-stakes situations like lockouts at 3:00 AM or emergencies, making human coverage a key differentiator. Extend Team offers shared services packages priced roughly $25–$100 per unit, onboarding in 3–10 days, plus direct staffing for specialized roles; an AI-only model is planned for flexible, seasonal use.

00:00 Welcome and Introductions

00:57 Mike’s Industry Journey

02:43 People First and Education

03:45 Extend Team Shared Services

05:43 AI vs Humans in Guest Service

08:34 When to Use Staffing or AI

10:54 Onboarding and Service Pillars

14:07 Pricing and Scaling Packages

16:09 AI Investment and Margins

17:42 AI Only Model and Risk

20:25 How to Contact Extend Team

21:02 Closing Thanks and Wrap Up

Steve Schwab interviews Tim Rosolio, VP of Vacation Rental Partnerships at Expedia Group, about VRBO’s recent transition to a common Expedia tech stack that expands VRBO inventory across Expedia demand and a growing B2B network (including Uber), enables hotel-style promotional tools, and intensifies a focus on quality and trust to reduce traveler anxiety. Rosolio explains how quality signals—acceptance rate, cancellation rate, and reviews—drive conversion, badges, and search ranking, with last-minute cancellations the fastest way to lose position. They discuss VRBO Care’s protections (accuracy, 24/7 assistance, fraud protection, rebooking support) and common failure points like SNAD and denied entry. Rosolio notes operators delivering consistent experiences are winning as weaker supply exits, and highlights conversion drivers like strong photos, disclosed amenities, and tangible hospitality upgrades. They also cover distribution shifts, upcoming flight-plus-rental packaging, AI features (chatbots, Q&A, review summaries, natural language search), and preparing for AI-based discovery.

00:00 Welcome and Introductions

01:09 Tim as a Host

02:23 Expedia VRBO Strategy

04:41 Trust and Quality Shift

08:14 Vrbo Care Explained

10:13 Ranking and Quality Signals

13:11 Conversion Boosting Amenities

15:37 Distribution Channels Today

18:16 AI Reality Check

21:41 What Works and Whats Next

22:41 OTA vs Book Direct

24:07 Final Tip and Wrap Up

In this episode of Casago Keynotes, host Steve Schwab sits down with Jennifer Hsieh, Managing Vice President and Global Category Leader for Premium and Endorsed Brands at Marriott International.

Jennifer leads the strategy behind some of Marriott’s most influential brand extensions, including Marriott Homes & Villas and the broader Marriott Bonvoy ecosystem. In a wide-ranging conversation designed specifically for professional property managers and homeowners, she explains how Marriott successfully entered the vacation rental space without compromising brand trust—or the uniqueness guests expect from private homes.

Key Topics Covered

• Why Marriott Entered Homes & Villas
  The consumer insight that drove the strategy: nearly 27% of Marriott Bonvoy guests were leaving the ecosystem to book short-term rentals elsewhere—and how that gap became an opportunity.
• Standards vs. Standardization
  Why guests do not want cookie-cutter homes, but do demand consistent cleanliness, safety, reliability, and service recovery—and how Marriott enforces that balance globally.
• What Qualifies a Home (and What Disqualifies One)
  Jennifer breaks down the “signals of quality” Marriott looks for, from interior design coherence to maintenance details, outdoor spaces, and neighborhood context.
• The Power of Professional Property Management
  Why Marriott partners exclusively with professional operators—and how that model protects homeowners, elevates guest experience, and enables scalable quality control.
• The Role of Reviews, Scores, and Algorithms
  How guest feedback directly influences visibility, placement, and long-term performance within the Marriott Homes & Villas platform.
• Loyalty as a Demand Engine
  With over 45% of bookings involving points usage, Jennifer explains how Bonvoy drives high-quality demand—and why Marriott guests tend to be better, more respectful renters.
• AI Search and Differentiation
  What generative AI means for homeowners, why detailed property descriptions matter more than ever, and how features—not price alone—will increasingly drive bookings.
• Where Hospitality Must Stay Human
  Why technology should handle transactions—but people still define memorable stays, service recovery, and five-star reviews.

Key Takeaway for Homeowners

Quality over quantity. Homes that deliver consistent excellence—supported by strong operators and human-led service—will continue to outperform as global brands like Marriott shape the future of vacation rentals.

This episode offers a rare, inside look at how the world’s largest hospitality company evaluates homes, partners with operators, and protects long-term value for homeowners in an increasingly competitive market. 

Enhancing Revenue Management and Owner Experience with Wheelhouse: An Interview with Matt Hope

In this episode, Steve Schwab, founder of Casago, interviews Matt Hope, VP of Revenue Management and Analytics at Vacasa and founder and CEO of Wheelhouse, about the recent implementation of Wheelhouse into Vacasa. They discuss the benefits and challenges of this integration, particularly how it simplifies and improves revenue management for homeowners and franchise partners. The conversation also covers the impact on local teams, the transition process, homeowner satisfaction, and future enhancements. Key points include the significant reduction in support tickets, the importance of clear and owner-centric revenue management, and the role of continuous education and proactive communication in fostering strong relationships with homeowners.

00:00 Introduction and Guest Introduction
00:38 Integrating Wheelhouse into Vacasa
02:31 Challenges with Previous Systems
04:17 Benefits of Wheelhouse for Revenue Management
05:31 Owner Feedback and System Improvements
07:51 Future Plans and Owner Engagement
11:20 Designing Owner-Centric Revenue Management
30:44 Franchise Model and Local Teams
35:50 Closing Remarks and Future Outlook

Maximizing Vacation Rental Bookings with David Angotti: Strategies and Insights

In this episode of Keynote, host Steve Schwab interviews David Angotti, a multifaceted expert in web development, marketing, and property management. David discusses his extensive experience in the industry, which includes pioneering online learning platforms, working as a pilot, and managing properties. The conversation includes insights into the merger between vacasa and Casago, aiming to create a leading vacation rental website capable of competing with major platforms like Airbnb. They explore strategies for increasing website traffic, optimizing user experience, and leveraging relationships to drive bookings. David also emphasizes the importance of an owner-centric approach in decision-making. Together, they look forward to future opportunities and initiatives that will benefit homeowners and enhance the vacation rental ecosystem.

00:00 Introduction and Guest Introduction
00:07 David's Background and Experience
00:52 Property Management Insights
01:39 The Vacasa Opportunity
03:00 Marketing Strategies and Website Optimization
05:34 Conversion Rate Optimization
11:19 Future Opportunities and Content Marketing
12:52 The Orange Reto and Owner-Centric Approach
14:41 Final Thoughts and Conclusion

Empowering Homeowners with Owner-Centric Revenue Management

In this episode of Keynotes, hosted by Steve Schwab, founder of Casago, we dive into an insightful discussion with Andrew Kitchell, founder of Wheelhouse. The focus is on 'owner-centric' revenue management and its applications in the vacation rental industry. Andrew shares the journey of creating Wheelhouse, a platform designed to bring transparency and control over the revenue and performance of short-term rental properties. Key topics include the importance of empowering homeowners with clear, visual information, the impact of personalized pricing strategies, and the collaboration between Wheelhouse and Casago to enhance revenue management systems. The episode underscores the commitment to excellence, transparency, and rapid problem resolution, aiming to create a seamless, informed experience for homeowners.

00:00 Welcome and Introduction
01:04 Meet Andrew Kitchell: Founder of Wheelhouse
01:49 The Journey of Wheelhouse
04:17 Understanding Owner-Centric Revenue Management
07:43 The Casago and Wheelhouse Partnership
10:29 Empowering Homeowners with Data and Tools
15:21 Building a One-of-a-Kind Dashboard
21:40 Training and Empowerment for Better Service
25:24 Final Thoughts and Farewell

Transforming Vacation Home Management with Craig Rashkow: Introducing the Casago Franchise Model

In this episode of Keynotes, host Steve Schwab speaks with Craig Rashkow, a seasoned professional in the hospitality industry, about his recent transition to managing several Vacasa markets under the Casago franchise model. 

Craig shares his journey from working in operational roles to entering the vacation rental industry with Sonder and Roofstock. Emphasizing local support and personalized service, Craig discusses his vision for improving homeowner and guest experiences through better technology and operational practices. He also highlights the importance of community and interpersonal relationships in successful property management. Listen in to learn about the operational changes and improvements Craig plans to implement as part of the Casago team.

Reach out to Craig at *1-312-504-3462* or *[email protected]*

00:00 Welcome to Keynotes with Steve Schwab

00:54 Meet Craig: A Journey in Hospitality

01:56 Transition to Casago: What Homeowners Need to Know

03:42 Building Strong Local Teams

05:31 Craig's Personal Touch: Family and Music

07:03 Operational Improvements for Homeowners

09:57 The Importance of Local Decision Making

12:58 The Orange Credo: Stewardship and Values

14:27 How to Reach Craig and Final Thoughts

The Inspiring Journey of Hospitality. 

In this episode, Steve Schwab, founder and CEO of Casago, sits down with Kish, Jay, and Shirin Kanji, the newest partners of Casago, to discuss the legacy and future of their family business, Impact Properties. They delve into the rich history of their family's move from India to Africa and ultimately to the United States, where they ventured into the hospitality industry. The trio shares personal anecdotes, their long-term vision focusing on owner-centric values, excellence, and anticipation in the business. Highlights include their experiences at Casago University, the importance of transparency and relationship-building in hospitality, and their plans for embracing the team and developing their strategy for success. 

For more information, please email: [email protected]

00:00 Introduction and Guest Introductions

02:09 Kish's Family Journey into Hospitality

09:48 Shirin and Jay's Perspectives

11:19 The Importance of Relationships in Business

17:59 Experiences at Casago University

27:38 Vision for Homeowners and Future Plans

34:23 Closing Remarks and Contact Information

Owner-Centric Property Management with Michael Austad of Casago

In this episode of Keynotes, host Steve Schwab talks with Michael Austad, owner of Casago in Willamette Valley, about his transition from a long career in retail to the hospitality industry. Michael discusses the importance of simplicity, authenticity, and owner-centric property management. Highlighting Casago's unique value, Michael illustrates how the company maintains a delicate balance between the advantages of a large corporation and the personalized touch of a local owner, fostering close relationships and effective management for homeowners.

00:00 Introduction to Keynotes Podcast
00:39 Meet Michael Austad: From Retail to Casago
02:06 Transition to Hospitality Industry
03:25 Choosing Casago: Values Over Profit
05:16 The KISS Principle in Vacation Rentals
06:31 Authentic Conversations and Relationships
06:51 Casago's Unique Value Proposition
08:52 Owner-Centric Approach
10:01 Advocating for Homeowners
10:50 Handling Homeowner Issues
12:04 Contacting Casago for Property Management
12:52 Conclusion and Final Thoughts