2-5 p.m.
Registration Open (The Ritz-Carlton Ballroom Foyer)
3-4 p.m.
A Case Study of +25 Years of Failure of National Hospitality Management Companies: Lessons Learned for Vacation Rental Executives (optional session)
On December 30th, 2024, Vacasa announced its proposed merger with Casago, marking the end of its journey as a public company. What most people don't know is that Aimbridge Hospitality, the largest hotel management company in the US (managing over 1,500 hotels at its peak) announced an out-of-court bankruptcy restructuring 2 weeks later on January 16, 2025.
Join us for a detailed case study and Q&A discussion on the rise and fall of +25 years of attempts to create national hospitality management companies across the vacation rental, hotel and restaurant industries. The case study covers the journeys of 10 different hospitality companies through discussion with executives, employees, owners, investors and bankers across the hospitality industry.
Learn from their biggest mistakes and how to position your vacation rental business for long-term success.
Speaker: Ashley Ching, Founder & CEO, Inhaven
4-5 p.m.
Fireside Chat with Sarah: Undercover Boss The Vacation Rental Edition (optional session)
When’s the last time you actually slept in one of the homes you manage? In this laid-back fireside chat, we’ll talk about why staying in your own properties is one of the smartest (and most overlooked) ways to uncover what guests really experience. From missing USB plugs to mysterious light switches, we’ll cover a punchy checklist of what to look for—plus the tiny things that make a huge difference in reviews and rebookings. Spoiler alert: it’s probably not the throw pillows.
Speaker: Sarah Bradford, Consultant and Industry Luminary
5-7 p.m.
Registration Open (Starr Bar)
6-8 p.m.
Reception (sponsored by TRACK)
7 a.m.–4 p.m.
Registration Hours
7:30–8:30 a.m.
Breakfast (sponsored by Grand Welcome)
8:30–9 a.m.
Welcome to the Executive Summit!
9–10 a.m.
Stop Watching, Start Winning: AI Strategies You Can Implement Before This Conference Ends
AI isn’t the future—it’s the now, and the property managers who embrace it will gain an undeniable edge. This fast-paced, no-fluff keynote skips the speculation about where AI might go in five years and instead delivers immediately actionable strategies that drive efficiency, profitability, and competitive advantage today.
Whether you’re looking to streamline operations, make better data-driven decisions, or scale without adding overhead, this session will equip you with practical tools you can implement before you leave the room. No jargon, no endless hype—just clear, tactical takeaways designed for real-world impact. AI is already reshaping the vacation rental industry, and those who understand how to leverage it will outpace the competition.
If you’re tired of theoretical discussions and want actual results, this is the session you’ve been waiting for. Walk away with strategies that save time, increase revenue, and position your business for long-term success.
Speaker: David Angotti, Chief Evangelist, Guesty
10–10:30 a.m.
Humans at the Helm: Scaling Empathy in the Age of AI
Fresh off the historic Casago/Vacasa merger, Steve Schwab joins David Angotti to talk about a future that isn’t just automated—but elevated. In this candid fireside chat, they’ll explore how AI can remove friction, empower frontline teams, and create space for more authentic human connection. From the boardroom to the booking process, discover how top operators are using AI not to replace people—but to help them be more human and deliver exceptional hospitality.
Speakers:
David Angotti, Chief Evangelist, Guesty
Steve Schwab, Founder and CEO, Casago
10:30–11 a.m.
Networking Break with Exhibitors
11 a.m.–12 p.m.
How to Reclaim Your Time and Attention in a World That Steals Both
In a market where competition is fierce and demands are relentless, success isn’t just about strategy—it’s about sustainability. As high-achieving entrepreneurs, it’s easy to pour everything into your business, only to find yourself running on empty.
With Steven, we’ll explore how to cultivate a thriving business and a thriving life—so you’re not just more productive, but more present, energized, and effective. Discover how to steward your time, attention, and well-being in a way that fuels both your success and your fulfillment.
Speaker: Steven Lawson, CEO & Founder, Monk Manual
12–12:15 p.m.
Rachel's Book Club
Join us for a relaxed and engaging networking session designed to inspire and connect. Rachel Alday, known for curating an in-house library and motivating her team through reading incentives, will share how she uses books as powerful tools for leadership and professional growth. Discover how Rachel cultivates a culture of continuous learning—and how you can do the same within your own team. All Executive Summit attendees are encouraged to bring two books that have influenced your journey as a leader, decision maker, or simply as a person. Share your favorites, swap stories, and exchange books with fellow attendees in this informal, interactive gathering.
Speaker: Rachel Alday, Co-founder, Abode Luxury Rentals
12:15–1:45 p.m.
Lunch (sponsored by Savvy, formerly bnbfinder)
12:15–1:45 p.m.
Networking Break with Exhibitors
1:45–2:30 p.m.
Deal or No Deal: When Do You Buy?
Hear directly from companies actively seeking acquisitions about the strategies they use to enter new markets. Discover what business owners should be thinking about now, especially if you're considering exiting within the next five years. Our expert panel will dive into key considerations for owners, including industry consolidation trends, what buyers are looking for, and why they decide to pass. Don't miss this opportunity to get strategic insights for navigating the acquisition landscape.
Moderator: Jacobie Olin, President, C2G Advisors
Speakers:
Dustin Abney, CEO, Portoro
Jakob Dwyer, CEO, Awayday Vacation Rentals
Rafi Haramati, Managing Director, Garnett Station Partners
Joesph Riley, President, Casago
2:30–3 p.m.
Networking Break with Exhibitors
3–4 p.m.
Networking Roundtables
Join us for our networking roundtables, a forum for networking and discussion on key industry topics. Choose from pre-selected topics at designated tables, each led by an expert facilitator to guide conversations and spark insights. This is your chance to delve into emerging trends, share experiences, build valuable connections, and get those tough questions answered with your peers. Here you can find the list of topics:
- Insurance Insights & Programs for Property Managers
- Managing Merchant Risk and Fraud
- Tackling Revenue Challenges Together
- Financial Margins and KPIs
- Understand the Return on Your Investment
- Adoption of Tech & Your Tech Stack
- AI & Automation as a Lever for Revenue Optimization
- Owner Growth
- Elevating Retention & Acquisition Strategies for Guests & Owners
- Scaling Operations without Losing Control
- Concierge
- Guest Communications
- State of the STR Industry
- Create 5-Star Stays at Scale
- Session Follow Up with Steven Lawson
- KPIs within Your Organization
- Hotel-Style Loyalty for VRMs
4:05–5:15 p.m.
What I’d Tell My Younger VRM-Self If I Could Do It All Over Again
Sarah offers a refreshingly honest look back at her experience in the short term vacation rental industry as owner of two successful businesses she sold at their peak in 2022. She shares the surprises and challenges she faced, from managing homeowner expectations to navigating financial ups and downs. With a blend of humor and vulnerability, Sarah reflects on the lessons she’s learned and the turning points that helped her grow as a business owner. Gain practical insights and connect with others who understand the unique rewards and challenges of running a short term vacation rental business.
Speaker: Sarah Bradford, Consultant and Industry Luminary
5:15 p.m.
Closing Reflections
5:30–7:30 p.m.
Reception (sponsored by BookingPal)
7:30–11 a.m.
Registration Open
7:30–8:30 a.m.
Breakfast (sponsored by Summer) and Meet the VRMA Board
8:30–8:45 a.m.
Welcome and Relaunch of VRMA Advocacy Fund
8:45–9:45 a.m.
The VR Exec’s Reputation Currency: Building a High-Value Personal Brand for Maximum ROI
Your reputation is more than a reflection—it's a powerful asset. In this session designed for CEOs and senior leaders, discover how to build an authentic personal brand that drives trust, influence, and business results without adding to your workload. Learn how to turn everyday leadership moments into strategic visibility, use tech-savvy tools to stay relevant, and position yourself as a high-value authority with homeowners, investors, and your team.
Speaker: Amber Hurdle, Chief Executive Officer, Amber Hurdle Consulting
9:45–10 a.m.
Networking Break with Exhibitors
10–10:45 a.m.
Vacation Rentals in the Crosswinds: Trends, Recession Watch, and What’s Next
In this session, we’ll use today's headlines to provide a clear picture of what you can expect in 2025 and 2026. We’ll analyze the broader trends shaping the future, including potential "collateral damage"—how policies that may not directly impact you still have ripple effects across the industry. Gain insights into navigating a rapidly evolving landscape, understanding how current developments will influence your strategy, and identifying opportunities amidst the chaos. This session will equip you with the foresight to anticipate changes and make informed decisions for the years ahead.
Moderator: Matt Varabkanich, Sr. Research Associate, Cleveland Research Company
Speakers:
John deRoulet, Head of Revenue Management Education, Wheelhouse
Rohit Bezewada, CEO, AirDNA
Jason Sprenkle, CEO, Key Data Dashboard
10:45 a.m.–11:45 a.m.
Using Data to Build a Scalable VR Business
Scaling your business profitably is no small feat. In this session, we’ll explore how to pivot your business and implement strategic changes that ensure long-term profitability. Learn about new models for achieving scalable and sustainable success and gain valuable insights from lessons learned through failure including why what got you here won’t necessarily get you there. We’ll dive into how to use the data you’re already capturing to run your business more efficiently, making smarter decisions and setting the stage for growth.
Moderators:
Steve Trover, Founder, Better Talent
Speakers:
Eric Breon, Founder, Fairly
Ben Gross, Co-Founder and CEO, Minty Living
Jennifer Mucha, Founder and President, Arrived
Michael Pedenko, Co-Founder/ Associate Broker, Porter Vacation Rental Management
11:45 a.m.–12 p.m.
Closing and Key Takeaways