2026 User Conference

About

Set sail with us at the beautiful Annapolis Waterfront Hotel for the Barefoot User Conference, a event designed to inspire, educate, and connect our clients and partners. Our goal is to provide you with the essential tools and knowledge to steer your business toward a more profitable and efficient future. This year’s theme, “Charting Your Course: Navigating Towards Success with Barefoot,” focuses on giving you the strategies and insights to confidently guide your business forward.

A centerpiece of the conference is an exclusive Naval Academy tour, where attendees will gain firsthand insights into how the Navy equips teams and individuals for success. You will learn how one of the world's most respected institutions fosters exceptional teamwork, drives collective achievement, and grows great individuals. Discover practical strategies to anchor these lessons in your own team and organization.

Through interactive workshops, engaging sessions, and meaningful discussions, attendees will explore ways to strengthen leadership skills, drive team performance, and foster a culture of excellence within their organizations. With Annapolis’ historic waterfront as your backdrop, this conference offers an unmatched opportunity to learn, connect, and be inspired.

$695

Buy 2 Get 1 free

2.5 days of engaging sessions and workshops focused on leadership, team development, and property management best practices.
Exclusive Naval Academy Leadership Tour – explore the Academy’s storied history and uncover leadership lessons that can transform your team. *see the access requirements here.
Dinner at the Admirals Club – connect with peers and Barefoot team members. *see the access requirements here.
Opportunities to network with industry professionals and share strategies and experiences.
Morning breakfasts, lunches, coffee breaks, and light refreshments throughout the conference.
Conference materials and swag to enhance your experience and takeaways.

Conference Schedule (Subject to change)

Wednesday, March 4, 2026
	Session	Location	Description
1 p.m. - 5:00 p.m.	Office Hours / Q&A	Breakout Room	First come first served, 20 min sessions available once registered
4:30 p.m. – 5:30 p.m.	CEO & Leadership Book Discussion	Main Room	Guided discussion of 'Leaders Eat Last' focusing on leadership resilience and culture development.
6:00 p.m. – 7:30 p.m.	Kickoff Party Cocktails	Hotel Lounge	Welcome reception for attendees to connect before sessions begin.

Thursday, March 5, 2026
	Session	Location	Description
7:30 a.m. –8:30 a.m.	Registration & Breakfast	Main Room	Conference check‑in and light breakfast.
8:30 a.m. –9:15 a.m.	Welcome & Opening Remarks	Main Room	Opening statements, conference orientation, introductions
9:15 a.m. –10:00 a.m.	Keynote: Julie Brinkman, CEO of Beyond	Main Room	Beyond CEO Julie Brinkman will share hard-earned lessons from leading through disruption, change, and adversity - using the lens of the last few years as defining moments to help show you how to shape strong and nimble teams - ones that are built for sustainability and growth. Rather than focusing on crisis management alone, the session explores how leaders can turn periods of instability into catalysts for resilience, trust, and long-term business performance. This session is designed for founders, operators, and team leaders who want to build resilient, high-performing teams that don’t just survive disruption, but are stronger because of it.
10:00 a.m. –10:30 a.m.	Break and Networking
10:30 a.m. –11:15 a.m.	Product Roadmap 2026–2027 and Vote for Enhancements	Main Room	Feature updates and enhancements coming to Barefoot to support operations.
11:15 a.m.–12:00 p.m.	Partner Connection	Main Room	Technology partners present updates for 2026, including AI.
12:00 p.m. –1:00 p.m.	Lunch and Networking	Main Room
1:00 a.m. –2:00 p.m.	Signal In, Strategy Out: A Modern Framework for Revenue Management	Main Room	With so much industry data available, it can be hard to know which signals truly matter. This session introduces a clear framework for using revenue management signals across three levels — manually interpreted signals, automated signals, and emerging micro-signals. Through real-world examples, Beyond will show how to evaluate pricing, benchmarking, and channel visibility challenges, and how to turn those insights into a smarter revenue strategy using AI and efficiency tools.
2:00 p.m. –2:30 p.m.	Keeping the Balance: The Strategies and Date Behind the New Search Marketing Environment	Main Room	As AI-driven search experiences reshape how travelers discover vacation rentals, marketers must evolve thoughtfully—integrating new, data-informed strategies without losing sight of core SEO principles. This session explores how to optimize for emerging AI interfaces while maintaining the proven tactics that continue to drive rankings, traffic, and bookings. Attendees will gain practical insights to keep their websites competitive, future-ready, and firmly rooted in what works.
2:30 a.m. -3:00 a.m.	Bad Stays and Bourbon Chasers: Your Worst Guest Stories	Main Room	Like a good bourbon, some guest stays go down smooth, and others leave you on the rocks. We know you’ve seen it all, and now it’s time to share! Join the Safely team for cocktails and commiseration as we swap jaw-dropping stories of the good, the bad, and the downright outrageous. Laugh, learn, and leave with insider tips to help you handle (and hopefully prevent) future shenanigans. Come for the bourbon, stay for the stories!
3:00 p.m. –3:30 p.m.	Travel to Naval Academy	Naval Academy	Walk to campus
3:30 p.m. –5:30 p.m.	Naval Academy Tour	Naval Academy	Private guided tour of the Naval Academy campus.
5:30 p.m. –6:00 p.m.	Cocktail Reception and Presentation	Naval Academy	Reception with Naval Academy Representative
6:00 p.m. –8:00 p.m.	Dinner at the Officers’ Club	Naval Academy	Seated Group Dinner

Friday, March 6, 2026
	Session	Location	Description
7:30 a.m. - 8:30 a.m.	Breakfast & Networking	—	Morning meal and informal networking.
8:30 a.m. - 9:00 p.m.	Technical Session	Main Room	Technical deep dive into integration structure, authentication, and system operations.
8:30 a.m. - 9:00 a.m.	Building Operational Efficiencies in Barefoot	Breakout Room	Best Practices, Automations and Operational Tools
8:30 a.m. - 9:00 a.m.	Client Success Stories	Main Room	Innovative Things Barefoot Clients are Doing
9:00 a.m.-12:00 p.m.	In‑Depth Accounting Lab	Breakout Room	Advanced trust accounting workshop with real-world scenarios.
9:00 a.m. -9:30 a.m.	Refining Your Search Roadmap: Follow-Up Roundtables With RealTech	Main Room	You’ve seen the data behind the new search landscape—now let’s apply it to your inventory. Join Britt Benson-Greer and the RealTech team for a dedicated follow-up to yesterday’s presentation. This interactive roundtable offers a space for property managers to discuss and evaluate search strategies with RealTech's experts to ensure they are perfectly balanced for both search engines and the emerging AI interfaces.
9:30 a.m. -10:00 a.m.	AI Discussion and Feedback	Main Room	Discussion about AI in the industry and within Barefoot
10:00 a.m. - 10:30 a.m.	Chesapeeking at the Data: What 2026 Has in Store for Your Vacation Rental Market	Main Room	In this presentation, tailored to attendees, you'll find information about your market and the general feel for where this year is headed in a way that only Key Data can provide. Navigating the numbers is hard, but this presentation will help you chart your course and get your heading in time to impact your season. Presented by Daniel Leifeld
10:30 a.m. - 11:00 a.m.	The Siren’s Song of AI: Avoiding Distractions as Search Engines Change	Main Room	From the shoreline, a harmonic voice carries across the water to your ship. It grows louder as you steer toward it, smoother, more confident, impossible to ignore. It sings, “Your website won’t show up in AI without us.” You follow it, but don’t see the rocks ... until it’s too late. "Can you make my website ready for AI?” It’s the question for 2026. AI has become the siren’s song of modern marketing. Alas, ignore those sirens and listen to a 20-year vacation rental marketing veteran instead! Let’s start with how AI works behind the scenes, including how bots evaluate your site to determine whether to show your content. From there, we’ll look at how Google is blending traditional SEO with AI-driven results, and what that means for your visibility. When someone asks ChatGPT, Gemini, or Claude to recommend a vacation spot, you’ll understand exactly why certain brands surface and others never, and what you need to do about it The truth is, being “ready for AI” isn’t something a marketing company can flip a switch on. Property managers have just as much work to do, if not more, and much of it can be done right inside Barefoot! Presented by Paul Hanak from ICND.
11:00 a.m. -11:30 p.m.	Barefoot Tips and Tricks	Main Room	Staff members share their favorite tips and tricks
11:30 a.m. -12:00 p.m.	Creating an Upsell Culture	Main Room	Adding Revenue through Upsell
12:00 p.m. - 12:30 p.m.	Lunch	Main Room
12:30 p.m. - 1:00 p.m.	Understanding & Preventing Vacation Rental Chargebacks, Supported by Yapstone & Barefoot	Main Room	This presentation provides a comprehensive overview of chargebacks in the vacation rental industry and why they matter for property managers and operators. It begins by defining what chargebacks are and outlining the full chargeback process, from a guest dispute through bank review and final resolution. The presentation highlights how Yapstone Chargeback Specialists assist partners by managing disputes, submitting evidence, and reducing financial and operational risk. Attendees gain a clear understanding of the different types of chargebacks, including fraud, no-show, and service-related disputes, along with common culprits such as unclear policies, miscommunication, or unauthorized transactions. The presentation explains why chargebacks occur and how they can impact revenue, reputation, and operational efficiency. It concludes with actionable best practices to help prevent chargebacks, including clear rental agreements, transparent communication, proper documentation, and proactive guest support. Additional online resources are shared to help teams stay informed and continuously improve chargeback prevention strategies.
1:00 p.m. –1:45 p.m.	Leveraging the Unified Inbox	Main Room	Existing functionality, how to set up, what's coming next
1:00 p.m. –1:45 p.m.	Reporting in Barefoot	Breakout Room	Deep dive into various reports in Barefoot
1:45 p.m. –2:30 p.m.	OTA Strategy for 2026	Main Room	Getting real about the opportunities and challenges of working with OTAs
1:45 p.m. –2:30 p.m.	Guest and Owner Portal -- Mobile Ready	Breakout Room	Setting up the Mobile Ready Guest and Owner Portal & Feedback Session
2:30 p.m. –3:30 p.m.	Closing Session: What’s Next	Main Room	Final announcements and wrap‑up.

Barefoot User Conference

Charting Your Course:

Navigating Towards Success

with Barefoot

About

Client Registration

$695

Buy 2 Get 1 free

Conference Schedule (Subject to change)

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