Alex and Annie: The Real Women of Vacation Rentals

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In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered.
This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people?
For many vacation rental operators, marketing often defaults to the property itself. A home needs bookings, a calendar has gaps, or a listing needs more visibility, so the message becomes centered around the unit. While property marketing still has a place, Orlie explains why stronger results often come from understanding the guest first.
That means looking beyond the booking and thinking about who the guest is, why they are traveling, what they care about, and how operators can use that information to create more relevant communication.
The conversation also explores why guest data is only valuable when operators can actually use it. Orlie breaks down how Lasoh is building a guest marketing system that helps operators collect, organize, and activate guest data through AI-supported campaigns, smarter segmentation, and more personalized messaging.
Instead of expecting teams to manually sort through data, build every campaign from scratch, and figure out what message should go to which guest, Lasoh is working to make that process more accessible. The goal is to help operators create more meaningful marketing, drive repeat bookings, and grow revenue without adding more pressure to already busy teams.
Episode Chapters
01:16 - Stop marketing properties and start marketing to people
01:41 - Why guest-first marketing needs better data
03:53 - Property management systems vs. guest marketing systems
06:47 - Turning guest data into action with Lasoh
08:24 - Using AI to create revenue-driving campaigns
12:28 - Smarter segmentation and fewer, better emails
15:54 - How AI agents support vacation rental marketing
18:40 - Saving time and growing revenue without adding more work
23:42 - One-to-all, one-to-some, and one-to-one marketing
26:44 - Lasoh’s founding member program
30:35 - What founding members can expect
This episode is a valuable listen for anyone thinking about how to make vacation rental marketing more relevant, more efficient, and more connected to the people behind each stay.
Learn more about Lasoh:
Website: https://lasoh.io/
LinkedIn: https://www.linkedin.com/company/lasoh/
Facebook: https://www.facebook.com/people/Lasohio/61575721958679/
Instagram: https://www.instagram.com/lasoh.io
Connect with Orlie:
LinkedIn: https://www.linkedin.com/in/orliebenjamin/
Facebook: https://www.facebook.com/profile.php?id=61585160391720
Instagram: https://www.instagram.com/orlie.benjamin/ 
✨ Exclusive Offer to Alex & Annie Listeners: 
Turn every guest interaction into more revenue with Lasoh.
Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through July 31, 2026.
👉 Learn more: https://explore.lasoh.io/alex-annie
#vacationrentals #vacationrentalmarketing #directbookings

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In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations.
James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury brand focused on ski markets. After operating across different types of destinations, the company made the decision to narrow its focus and go deeper in the markets where it could build stronger operations, deeper owner relationships, and more consistent guest experiences.
That shift became one of the central themes of the conversation: bigger is not always better. James explains why going deeper in the right markets can be stronger than expanding everywhere at once, and why sustainable growth requires the right homes, the right owners, strong teams, and the operational discipline to support the experience being promised.
Episode Chapters:
04:00 - Choosing Focus Over Footprint
05:39 - The Challenge of Scaling Luxury Vacation Rentals
16:59 - Working with the Right Owners
20:04 - What Consistency Means in Luxury
21:32 - AI, Technology, and High-Touch Service
27:36 - Direct Bookings and Luxury Travel Advisors
39:22 - Regulation in Ski Markets
46:12 - Why Undercharging Can Hurt the Business
Connect with James:
LinkedIn: https://www.linkedin.com/in/jamesalansmith/ 
Connect with InvitedHome:
Website: https://invitedhome.com 
Instagram: https://www.instagram.com/invitedhome/
Facebook: https://www.facebook.com/InvitedHome
LinkedIn: https://www.linkedin.com/company/invitedhome/
✨ Exclusive Offer to Alex & Annie Listeners: 
Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 
Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 
#vacationrentals #shorttermrentals #skimarkets

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In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations.
Paul and Amanda share how Call Center Solutions grew out of a real hospitality staffing challenge and how their nearshore team in Montego Bay, Jamaica now supports vacation rental and hotel companies with reservations, outbound calls, after-hours support, back-office work, and more.
The conversation also explores why human connection still plays such an important role in hospitality, even as AI becomes a bigger part of guest communication. Paul and Amanda break down how operators can use technology to support their teams while still creating the kind of guest experience that builds trust, drives bookings, and keeps people coming back.
We discuss:
05:59 - How Call Center Solutions got its start in the hospitality space
05:59 - Why staffing continues to be a challenge for reservation and guest service teams
12:00 - How nearshore support can help operators improve consistency and coverage
10:20 - The role of redundancy during storms, outages, and operational disruptions
14:40 - Where AI fits into guest communication and agent support
16:01 - Why human connection still matters in vacation rental hospitality
13:20 - The importance of training, knowledge bases, and quality assurance
44:41 - How support teams can help identify gaps in the booking experience
28:21 - What operators should consider when outsourcing guest services
Connect with CCS:
Website Link: https://www.ccssuccess.com/
LinkedIn Link: https://www.linkedin.com/company/my-call-center-solutions/
Facebook Link: https://www.facebook.com/ccssuccess
Instagram Link: https://www.instagram.com/call.center.solutions/
Connect with Paul:
Email: [email protected]
Connect with Amanda:
LinkedIn: https://www.linkedin.com/in/amanda-szubert-8b26a033/ 

✨ Exclusive Offer to Alex & Annie Listeners: 
Improve efficiency and customer engagement with Call Center Solutions.
Get all setup and implementation fees waived when you let them know you heard about CCS from Alex & Annie.
👉 Get started: https://www.ccssuccess.com/ 
Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 
Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 
#vacationrentals #shorttermrentals #guestservices

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Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there.
In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools.
Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools.
Through his own property management experience, Chris saw how important it is for guests to clearly understand the value of booking direct at the moment they are making a decision. Operators may know that value, but it has to be visible, trustworthy, and easy for guests to act on.
We discuss:
00:06:13 - Why trust is central to direct booking conversion
00:09:43 - How price transparency can influence guest decisions
00:15:16 - What website traffic can reveal about booking behavior
00:28:12 - How operators can use data to improve pricing decisions
00:49:26 - Why direct booking strategy needs more than awareness
00:28:12 - How to strengthen conversations with owners using real data
00:42:31 - Why Chris believes quality and intentional growth still matter 
Whether you are trying to increase direct bookings, improve website conversion, or better understand how guests are making booking decisions, this episode offers a practical look at what operators can do to turn more interest into revenue.
Connect with Chris:
LinkedIn: https://www.linkedin.com/in/chriswalkerhhi/ 
Website: https://directbookingtools.com/

✨ Exclusive Offer to Alex & Annie Listeners: 
Strengthen your direct booking strategy with Direct Booking Tools.
Alex & Annie listeners get 50% off for the first 3 months.
👉 Get started: https://directbookingtools.com/alex-annie-landing-page/ 

Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie 

Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/  

Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.
👉 Access the offer here: https://explore.lasoh.io/alex-annie  

#vacationrentals #shorttermrentals #directbookings

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In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.
Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.
The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.
Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.
Episode Chapters:
02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide
10:06 - How Marriott Vacations Worldwide thinks about loyalty
11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings
18:53 - What vacation rental operators can learn from timeshare
19:30 - How brand standards help build guest trust
28:20 - Why lifetime value matters in the customer journey
29:00 - Viewing vacation ownership as a subscription business
31:09 - Using experiences to strengthen loyalty and engagement
40:11 - How Marriott Vacations Worldwide is using AI in sales training
41:41 - How AI is changing digital search and hospitality marketing
47:52 - Why prepaid vacations create resilience
51:43 - What is ahead for Marriott Vacations Worldwide
Connect with Mike:
LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094 
Instagram: https://www.instagram.com/thevacationdr/reels/ 
Connect with Marriott Vacations Worldwide:
Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/ 
Westin Vacation Club: https://www.instagram.com/westinvacationclub/ 
Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/ 
✨ Exclusive Offer to Alex & Annie Listeners:
Automate your short-term rental operations with Hospitable.
Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie
Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 
Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.
👉 Access the offer here: https://explore.lasoh.io/alex-annie 
#vacationrentals #shorttermrentals #timeshare