Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica.

This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality team that can support vacation rental businesses from hundreds of miles away.

Throughout the visit, Alex and Annie sit down with members of the CCS team across operations, HR, IT, and leadership to hear what the business looks like from the people running it every day. One theme keeps surfacing along the way: the importance of culture, connection, and making remote team members feel like a true extension of the companies they support.

Episode Chapters:

00:00 – Alex & Annie arrive at Call Center Solutions in Montego Bay

02:49 – How CCS started in Jamaica and grew beyond the original experiment

06:50 – What onboarding and training a remote hospitality team actually looks like

11:36 – Meet the operations team: culture, customer service, and what makes a great agent

20:47 – Inside HR: hiring, employee support, and building a team people want to stay with

29:42 – The IT and infrastructure keeping the operation running

34:21 – Beachside reflections on culture, connection, and hospitality

41:30 – Beyond reservations: how CCS supports more of the operation

45:16 – How property managers can get started with a CCS team

Come along for a behind-the-scenes look at Call Center Solutions, the team they've built in Montego Bay, and a few uniquely Jamaican moments along the way.

Connect with Call Center Solutions:

Website: https://www.ccssuccess.com/

LinkedIn: https://www.linkedin.com/company/my-call-center-solutions/

Instagram: https://www.instagram.com/call.center.solutions/

✨ Exclusive Offers to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #guestexperience

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In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades.

Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves.

That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different.

Episode Chapters:

11:14 - Building customer relationships designed to last

17:15 - Why Ciirus has chosen measured growth over growth at all costs

18:28 - How independent ownership shapes investment in customers and technology

22:38 - Why vacation rental operations cannot automate everything

27:39 - Building a global team around specialized talent

32:49 - Helping property managers get more from their technology

38:14 - Why customer and employee satisfaction matter together

39:55 - Ciirus’ new mobile app, owner tools, and Booking.com integration

46:03 - How LoveRentals helps property managers expand their capabilities

54:59 - Finding vacation rental demand beyond the major OTAs

57:55 - Reaching guests through travel agents, wholesalers, and international markets

1:02:24 - What is next for the Ciirus platform

If you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business.

Connect with Josh & Vinny

Josh Parry: https://www.linkedin.com/in/josh-parry-47165997/

Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/

Connect with Ciirus

Website: https://ciirus.com/

✨ Exclusive Offers to Alex & Annie Listeners:

Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform.

Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast.

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie

#vacationrentals #shorttermrentals #vacationrentaltechnology

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In this episode, Annie is joined by Jinnie Randolph for a conversation with Cristiana Carpini, founder of the Women in Vacation Rental European Conference (WVREC), and Neely Khan, founder of Kahani.

Together, they explore the value of creating spaces where women can build trust, share openly, and form meaningful relationships that support both personal and professional growth. Cristiana shares the thinking behind WVREC, while Neely reflects on what made the first gathering feel so different and why that environment gave her the confidence to share a deeply personal story publicly for the first time.

They also look ahead to WVREC 2026 in Barcelona, how the event is evolving, and the larger community Cristiana and Neely hope to continue building around it.

Episode Chapters:
02:20 - The story behind the Women in Vacation Rental European Conference
09:23 - Why trust and vulnerability shaped the first WVREC
16:19 - Why Cristiana is keeping the event women-focused
18:28 - How deeper connections can lead to collaboration and opportunity
21:52 - What to expect from WVREC 2026 in Barcelona
24:52 - Cristiana and Neely’s upcoming storytelling project
28:00 - Making the case for investing in professional development
34:27 - What surprised Cristiana most about the first conference
40:31 - Final details for WVREC 2026

Connect with Cristiana:

LinkedIn: https://www.linkedin.com/in/cristiana-carpini-hospitality/

Connect with Neely:

LinkedIn: https://www.linkedin.com/in/neelykhan/

Learn more about WVREC: https://wvrec.eu/

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie

#vacationrentals #shorttermrentals #hospitality

Send us a message!

Welcome to Episode 300 of the Alex & Annie Podcast! 🎉

Three hundred conversations, countless aha moments, plenty of industry debates, and a front-row seat to some of the biggest shifts vacation rentals have seen over the last several years.

This is such a huge milestone for us ⭐

To celebrate, we knew we wanted to bring back someone who has been part of the Alex & Annie journey since the early days.

We’re fortunate to have several people who have supported us along the way, and for this milestone, longtime friend of the show Terry Whyte returns for a conversation about how far the vacation rental industry has come and where it may be headed next.

Terry revisits predictions from his past appearances, including his views on technology, all-in-one platforms, loyalty, and distribution. He shares what he got right, what he would revise today, and how AI has changed the conversation.

Through it all, Terry keeps coming back to the fundamentals: quality properties, strong technology, smart distribution, customer care, and real human hospitality.

And because this is Episode 300, Alex & Annie also reflect on the journey so far and share a glimpse of what comes next for the podcast.

Here’s to 300 episodes and the next chapter of Alex & Annie. 🥂

Episode Chapters

02:30 - Revisiting Terry’s past industry predictions
03:26 - How AI changed the vacation rental tech conversation
06:29 - Why technology is becoming more fragmented
08:29 - Where automation ends and human hospitality matters
16:31 - Why growth does not always mean adding more doors
18:35 - Why distribution matters more than ever
19:37 - Direct bookings, website traffic, and marketing
24:39 - Rethinking loyalty in vacation rentals
29:40 - Terry’s advice for operators today
30:39 - What will separate thriving property managers in the future
33:37 - The risk of relying on a single OTA
35:49 - Terry reflects on the Alex & Annie Podcast
39:44 - The industry shift that changed Terry’s business
41:23 - What comes next for Alex & Annie

Connect with Terry:

LinkedIn: https://www.linkedin.com/in/terry-whyte-4540633b/

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie

#vacationrentals #shorttermrentals #hospitality

Send us a message!

In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined again by Julie Brinkman, CEO of Beyond, to talk about why owner retention deserves the same level of attention as pricing, pacing, and acquisition.

Julie breaks down the metrics property managers should be watching, how unrealistic revenue expectations can create problems later in the relationship, and why adding new properties does not always tell the full story of business growth. She also answers real operator questions around high churn, founder-dependent owner relationships, and what retention can mean for the long-term value of a property management company.

Episode chapters:

01:43 - Building owner trust through consistent communication
05:03 - The owner retention metrics property managers should understand
12:19 - When growth hides a leaky owner bucket
15:49 - Revenue projections and owner expectations
22:30 - Added 40 properties, lost 26: is that really growth?
27:00 - Transferring founder trust as the company scales
32:10 - What high owner churn can mean for a future sale
35:10 - Using portfolio data to identify where attention is needed

Tune in for Episode 3 of Revenue Reality Check, brought to you by Beyond, and take a closer look at what owner churn may be telling you about the health of your business.

Connect with Julie:

LinkedIn: https://www.linkedin.com/in/jrbrinkman/

Connect with Beyond:

Website: https://beyondpricing.com/

LinkedIn: https://www.linkedin.com/company/beyond-pricing/

Instagram: https://www.instagram.com/beyondpricing/

Facebook: https://www.linkedin.com/company/beyond-pricing/

#vacationrentals #shorttermrentals #strindustry

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In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for operations.

Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating the people, properties, and workflows behind great hospitality. The conversation explores how rising guest expectations, greater owner scrutiny, and advances in technology are changing what it takes to operate well, and where vacation rental operations may be headed next.

Episode Chapters:

04:10 - Building a company property managers want to work with

12:00 - The early days of Breezeway and connecting operational workflows

14:40 - Why property managers should think differently about their relationship with the property

18:35 - How rising guest expectations are changing vacation rental standards

22:00 - Reviews, owner expectations, and the professionalization of the industry

25:11 - The growing importance of cleaners and third-party service providers

29:01 - Could robots eventually handle vacation rental turnovers?

33:31 - How AI is changing vacation rental operations

39:52 - Why Breezeway continues to go deeper on operations

As vacation rentals continue to mature, the operators who can deliver consistently behind the scenes will be better positioned to meet rising expectations from both guests and owners.

Connect with Jeremy:

LinkedIn: https://www.linkedin.com/in/jeremiahgall/

Connect with Breezeway:

Website: https://hubs.la/Q04tyWJL0

✨ Exclusive Offer to Alex & Annie Listeners:

Get 20% off your first three months of Breezeway if you sign up by September 30.

👉 Get started here: https://hubs.la/Q04tyWJL0

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

#vacationrentals #shorttermrentals #directbookings

Send us a message!

The vacation rental industry has changed dramatically over the years.

The technology is smarter, distribution is broader, competition is stronger, and AI is reshaping how operators work. But some of the most important parts of the business have not changed at all.

In this special reshare, Alex & Annie step into the guest seats with Tim Rosolio of Expedia Group’s Powering Travel Podcast for a conversation about what thoughtful growth looks like as the vacation rental industry continues to mature.

Recorded at one of Vrbo’s Vacation Rentals of the Year in New Hampshire, they reflect on what decades in the industry have taught them about building strong businesses, choosing technology intentionally, reaching new travelers, and keeping hospitality at the center of it all.

Episode Chapters:

02:11 - How Alex and Annie found their way into vacation rentals

06:28 - What has stayed constant as the industry has changed

09:10 - Growth at all costs vs. building a strong business

10:55 - What smaller operators need before they scale

15:52 - Has the vacation rental tech stack become too complicated?

20:00 - Expanding demand through new traveler segments and distribution

24:30 - The role of DMOs in introducing travelers to vacation rentals

28:03 - AI, technology, and the changing meaning of human touch

Whether you caught the original episode on Powering Travel or are hearing this conversation for the first time, this is a timely look at how the vacation rental industry is evolving and what operators should keep in focus as they grow.

Connect with Tim:

LinkedIn: https://www.linkedin.com/in/tim-rosolio-434b2a98/

Powering Travel Podcast:

Apple Podcast: https://podcasts.apple.com/us/podcast/powering-travel/id1620056867

Spotify: https://open.spotify.com/show/4gaaqGF4oxYzdhIF4MZzZv?si=58490146cf3a4b37

#vacationrentals #shorttermrentals #hospitality

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When an owner asks for more detail, questions why something was handled differently, or wonders why they were not told about an incident sooner, the question is usually about more than the immediate issue.

They want to know their property is in good hands.

In Episode 3 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Amanda Martins and Rachel Alday for a candid conversation about the moments that put owner trust, guest relationships, and an operator’s decision-making to the test.

From serious property incidents and liability concerns to difficult emails and guest complaints, Rachel and Amanda share what years of experience have taught them about responding when emotions are high and the stakes are even higher.

Episode Chapters:

02:25 - What Owners Really Mean When They Ask for More Detail

08:20 - Why Documentation Matters After a Serious Incident

17:07 - Why Consistency Builds Owner Trust

24:07 - Turning Guest Complaints Into Service Recovery

28:41 - When a Guest Complaint Becomes a Liability Issue

33:28 - How to Show Empathy Without Accepting Liability

37:47 - Why Reacting Too Quickly Can Make Things Worse

42:00 - Why You Need the Right Processes and Partners Before Something Goes Wrong

If you have ever received an email that made you want to respond immediately, only to realize five minutes later that deleting the draft was probably the better decision, this episode is for you.

Connect with Rachel Alday

LinkedIn: https://www.linkedin.com/in/rachelalday/

Connect with Amanda Martins
LinkedIn: https://www.linkedin.com/in/amandakatmartins/

Learn more about Safely

Website: https://safely.com/alex-and-annie
LinkedIn: https://www.linkedin.com/company/safely-stay/
Instagram: http://instagram.com/safely/
Facebook: https://www.facebook.com/safelyprotection

This episode’s cocktail: The Owner Manual
A Pour Decisions twist on an Old Fashioned made with bourbon, honey, bitters, and orange.

Stir it. Don’t shake it. And maybe finish the drink before replying to that owner email.

#vacationrentals #shorttermrentals #ownerrelations

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