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Who should attend?
- Invite Only
Host: Expedia and Women in Short Term Rentals supported by YHangry
Who should attend?
- Property Owners and Managers
Host: Trusted Stays and Guesty
Who should attend?
- Property Owners and Managers
Host: Justin Ford Director of Safety & Certification Programs at Breezeway International Vacation Rental Safety Expert
Guests say they want to book direct, but most abandon at checkout. In this interactive session, we’ll unpack the Payment Trust Gap—the moment where confidence breaks and OTAs win. You’ll analyse real booking experiences, identify the trust signals guests subconsciously look for, and walk away with practical, proven ways to make your payment flow feel as safe and seamless as the big platforms.
- Why guests hesitate at checkout—even when price and availability are right
- How OTAs have trained travellers to trust their payment experience over yours
- The exact trust signals that increase confidence and boost conversion
- How Wander achieved nearly 70% direct bookings—and what you can replicate immediately
Who should attend?
- Property managers and vacation rental operators
- Hospitality and revenue leaders focused on direct bookings
- Marketing, growth, and UX teams responsible for conversion
- Anyone frustrated by losing guests at the last step of the booking journey
Host: Emilia Sperandeo, VP of Sales, Wander
You will walk out of the workshop with 10 high-quality leads for you to go win a signed contract; we will walk through the tactical step-by-step approach to get there:
- Learn how to find high-quality property leads
- Learn how to accurately forecast their revenue
- Learn how to win homeowners using data
Who should attend?
- Property Managers looking to grow their portfolio
Host: Scott Sage, SVP of Marketing and CX, Airdna
Guests now expect hotel-style flexible cancellation, yet many operators still see it as a costly risk. This session shows how flexibility can be re-engineered as a paid add-on that boosts conversion, generates revenue, and builds owner confidence. Drawing on work with leading short-term rental operators, Louise Birritteri, CEO of Pikl, explains how to price and package cancellation options, identify the real revenue risk, and use insurance-enabled models to protect income. The focus is practical and commercial: replacing refunds and goodwill gestures with a clearly priced, profitable flexibility model.
Key takeaways
- How to measure the real P&L impact of cancellations
- Proven paid-flexibility models guests will accept
- Using protection and guarantees to safeguard income
- Positioning flexible cancellation to owners as a growth driver
- Real examples of increased booking value and loyalty
Who should attend?
- Property Owners and Managers
Host: Louise Birritteri, CEO, Pikl
Build or optimize a scalable, hands off short-stay rental business using the exact systems, software, and remote teams that power a 70+ property portfolio.
Running a growing short-stay rental portfolio doesn’t have to mean being on call 24/7 or tied to one location. In this highly interactive Learning Lab, you’ll get a behind the scenes breakdown of the complete tech stack and remote team structure used to operate 70+ properties entirely remotely. From property management systems and pricing tools to CRMs and AI employee training softwares, you’ll see how the right technology paired with the right people creates scale, consistency, and freedom.
This session goes beyond theory. After walking through each component of my tech stack, you’ll have the opportunity to engage directly with the partners themselves. Attendees will rotate into focused discussions with the vendors they’re most interested in, making this a hands-on, collaborative session designed to help you leave with clarity, confidence, and a roadmap you can implement immediately.
What you’ll learn:
- The full tech stack required to manage and scale a short-term rental portfolio remotely. Including PMS, pricing tools, CRMs, AI training platforms and how they all work together.
- How to hire, train, and retain a high-performing remote team that runs 100% of operations without constant owner involvement.
- Practical workflows and systems that reduce owner workload while improving guest experience and operational efficiency.
- How to evaluate, select, and implement the right technology partners for your business with direct access to vendors for real-time questions and insights.
Who should attend:
- This session is designed for short-stay rental property owners, operators, and managers who want to scale their businesses without scaling their stress. It’s ideal for hosts managing multiple properties, operators looking to systemise and go remote, and anyone serious about leveraging technology and teams to build a sustainable, hands-off short-stay rental business.
Host: Hailie Maarie, Founder & CEO, CMH BNB
In this session, Patryk will share the strategies he used on his journey to scaling to 150 units, including how he established himself as the go-to expert that homeowners actively seek out. He'll lead interactive workshop activities where you'll practise applying thought leadership principles and demonstrating expertise within your own local markets. You'll leave with actionable tactics you can implement immediately to start attracting inbound enquiries.
You’ll gain:
- Battle-tested strategies for growing your management company's inventory through inbound leads
- Practical methods for establishing yourself as the go-to expert in your market
- Hands-on techniques to position yourself as a local market authority and attract homeowners proactively
- Real-world examples of how to demonstrate thought leadership that converts into new business
Who should attend?
- Property managers and hosts looking to grow their portfolios through inbound lead generation rather than outbound prospecting
Host: Patryk Swietek, Owner, The Cohost Company
Most people use AI in short bursts. They ask questions, copy answers, and move on. The result is generic output, more noise, and no real impact on the business. In this Learning Lab, Mark Simpson will break down his actual AI tech stack and show you how to turn it into a single, working system that supports bookings, guest communication, and day-to-day operations.
This is not a tools overview or a prompt dump. You’ll learn how to connect prompts, projects, and workflows so AI understands your business, works in your voice, and produces consistent outputs you can reuse every day.
You’ll build this system live during the session. By the end, you’ll have a practical setup you can immediately use to reduce admin, improve consistency, and save hours every week while supporting more bookings. This lab is designed for operators who want AI to do real work inside the business, not become another experiment or distraction.
You’ll learn:
- How to create a Master Prompt and System Prompt so AI understands your business and responds in your voice
- How to organise ChatGPT Projects so you stop repeating yourself and can run ongoing work streams (pricing, comms, marketing, ops) in one place
- How to use Canvas to refine outputs properly (emails, SOPs, guest comms) and then turn the final version into a reusable System Prompt
- How to set Custom Instructions and build Custom GPTs so repeatable tasks become one click outputs
Who should attend?
- Hosts and operators who are busy and want AI to remove admin, not add another tool to learn
- Property managers who want to increase output without adding headcount
- Anyone responsible for guest comms, ops, or marketing who wants a repeatable setup, not random prompting
- People who have tried ChatGPT and felt the results were generic, inconsistent, or unreliable
Host: Mark Simpson, Founder, Boostly
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