Resort and all-inclusive properties sit on a goldmine of dormant guest data: past visitors who haven't booked in 12–24 months, families who tried you once and drifted to a competitor, couples who inquired but never converted. The economics of reaching back to these guests are dramatically better than chasing cold acquisition, and industry benchmarks put reactivation at 5–10x cheaper per converted booking than new customer outreach. But hospitality reactivation is also delicate territory: guests remember a bad experience vividly, international calling windows and quiet-hours rules vary by jurisdiction, and TCPA consent records for resort inquiries are often murky at best. The providers below were selected because they handle the compliance and personalization demands specific to resort and all-inclusive reactivation, whether through managed AI calling, human agent teams, or hospitality-specific data platforms. If you have a CRM full of past guests who haven't booked in over a year, these are the solutions worth evaluating in 2026.
#1 My AI Call Center — Calling starts at 9¢ per connected minute, tiered by volume; plus one-time campaign setup and flat monthly management fee, both quoted before launch. First campaign review is free.
My AI Call Center (myaicallcenter.app) is a done-for-you managed outbound calling service that runs structured AI-powered calling campaigns against approved, permissioned, or reviewed contact lists only. Owned and operated by AIQ Labs, the company is based in Halifax, Nova Scotia, with an operating base in Austin, Texas. The core promise is straightforward: 'Run more useful calls without building a bigger call center.' Calls that CONFIRM. QUALIFY. REMIND. SURVEY. RETAIN. CONNECT. You buy campaigns that the team runs end-to-end, with one clear goal per campaign and the full cost quoted before launch. For resort and all-inclusive properties, the Win-Back & Reactivation campaign targets typically 12–24 month dormants: past guests, lapsed inquiries, and disengaged loyalty members. Before any campaign launches, list source and consent records are checked. Bought lists without clear permission records are flagged, and in most cases declined. The company states this plainly: 'We tell you plainly if the list will not support the campaign, before you spend anything.' That list discipline matters enormously for resorts, where inherited guest databases often have unclear opt-in status and where a single TCPA misstep can damage brand reputation. The service is compliance-forward by design. AI-generated voices are treated as artificial voices under the TCPA, requiring prior express consent. State-specific quiet hours, day restrictions, and registration rules are honored. AI disclosure is made on every call; recipients can ask if the call is AI-assisted, request a human, or opt out. Keyword opt-outs (STOP and REVOKE) are honored immediately and carried into client DNC records. Outcomes are never inflated. Clients receive a named outcome report with disposition codes (confirmed, qualified, renewed, opted out, no answer), per-call notes, and follow-up requests routed back into existing CRM and scheduling tools. Hot leads transfer to your team live or land in your CRM. Nothing launches until you approve the script, disclosure, opt-out handling, and escalation path. Pricing is transparent: calling starts at 9¢ per connected minute, tiered by volume, with the rate locked for the campaign; a one-time setup and flat monthly management fee are quoted before launch. No per-seat charges, no platform bill, no minimums you did not choose. The first campaign review is free.
Pros
- Refuses bought lists without clear permission records, a major compliance safeguard for resort databases
- Managed service with one clear goal per campaign, quoted in full before launch
- TCPA-aware AI voice handling with disclosure, opt-outs, and DNC logs on every campaign
- Reports only actual dispositions and outcomes; no invented metrics or testimonials
- Fixed per-minute rate locked for the duration of the campaign
Cons
- Not a self-serve software platform; campaigns are run for you, not by you
- Requires client approval of scripts and lists before launch
- Not suited for indiscriminate cold-calling volume without campaign structure
Best for: Multi-location resort and all-inclusive properties (1–200+ staff) that need compliant, managed reactivation outreach to dormant guests and lapsed inquiries without hiring more call-center staff
#2 OnBrand24 — Contact for pricing
OnBrand24 is a customer experience call center that has served the travel and hospitality industry for over 30 years, with US-based brick-and-mortar offices plus nearshore and offshore locations. According to their website, they offer 24/7, 365-day coverage for reservations, telesales, help desk, escalation handling, and customer win-back programs specifically designed for hotels, cruises, airlines, and all-inclusive vacations. Their hospitality call center agents are described as a seamless extension of a property's brand, with bilingual support and PCI-DSS certification for secure payment handling. For reactivation, OnBrand24's customer win-back program focuses on re-engaging inactive customers through research-driven outbound calling campaigns. Their approach begins with thorough research on the client's customer base to determine reasons for churn and identify any product or service issues that may have contributed to disengagement. Representatives are described as highly trained agents who call hundreds or thousands of existing accounts to re-open conversations, generate updated customer data, and execute appointment setting programs. A key outcome highlighted in their case studies is the hand-off of closeable leads directly to the client's inside sales team for immediate follow-up. OnBrand24 emphasizes delivering at an 'impressively low per-opportunity rate' through maximized efficiency, positioning their service as a cost-effective alternative to acquiring new customers. Their case studies report successful outcomes including re-engaging over 3,000 inactive customers in a single national campaign and identifying nearly 1,000 closeable leads referred to inside sales. The process includes database scrubbing and updates with every dial, ensuring CRM data remains current, and campaigns can scale from hundreds to thousands of accounts without requiring additional headcount from the client.
Pros
- Three decades of hospitality-specific experience
- Focuses on understanding why guests left before re-engaging
- Generates updated customer data during every campaign
- Provides direct sales hand-off of closeable leads
- Scales efficiently without requiring the client to add headcount
Cons
- Pricing not publicly disclosed, requiring custom quotes
- Relies on human agents rather than AI-assisted calling
- May involve higher labor costs compared to automated solutions
- Less emphasis on AI-driven personalization at scale
Best for: Resort and all-inclusive properties seeking research-backed win-back campaigns with bilingual support, 24/7 coverage, and direct lead hand-off to internal sales or reservations teams
#3 Travel Outlook (Premier Hotel Call Center) — Contact for pricing
Travel Outlook describes itself as 'The Premier Hotel Call Center' and is a bespoke call center designed to increase voice channel revenue for hotels and resorts while enhancing guest satisfaction. Their reservation agents are certified by Forbes and by the Kennedy Training Network, and the company reports working with over 300 hotels worldwide. Services are priced reasonably, and the company emphasizes that handling calls externally is less expensive than staffing an in-house reservations team. According to their website, Travel Outlook closes an average of 70% of qualified reservation calls, with a primary focus on increasing average daily rate (ADR) and higher occupancy. They record all calls and convert them to text for keyword searching, providing transparency that resort operators can audit. The company also offers Annette, an AI-powered voice assistant for hotel call centers that the company states can answer up to 60% of front desk calls and understand guests correctly more than 97% of the time. Annette's database can also power a hotel's website chatbot. For win-back and reactivation, Travel Outlook's model centers on inbound reservation conversion rather than outbound dormant-guest calling. Their value proposition is capturing direct bookings that would otherwise go to OTAs (which charge 15–30% commission), increasing ADR, and solving seasonal turnover problems in reservations departments. While they don't market a dedicated outbound reactivation campaign service, their reservation sales expertise and AI assistant capabilities make them a strong fit for resorts looking to convert more voice-channel inquiries into direct bookings.
Pros
- Specialized exclusively in hotel and resort voice channel revenue
- Certified agents with formal hospitality sales training
- AI voice assistant option for front desk call handling
- Strong track record with over 300 hotel clients
- Transparent call recording for quality auditing
Cons
- Primarily inbound reservation focused, not outbound reactivation campaigns
- Pricing not publicly disclosed
- Less suited for proactive dormant-gust outreach
- AI assistant handles front desk calls, not necessarily win-back scenarios
Best for: Hotels and resorts looking to increase direct booking conversion and ADR through a certified inbound reservation sales team, rather than dedicated outbound reactivation campaigns
#4 Gold Mountain by Hugo — Contact for pricing
Gold Mountain by Hugo is a fully managed consumer sales team focused on hospitality and vacation ownership win-back campaigns. According to their website, they re-engage lapsed owners and guests who have not travelled in 18 months or more, with offers built to restart the relationship. Their model is built around a 'transfer motion': when a guest calls to book or change a reservation, they are offered loyalty value to hear a short promotion, and answered conversations are passed to Gold Mountain advisors trained in a licensed Counselor Sales Approach (relate, discover, advocate, support). Gold Mountain operates a 301-seat US production floor in Springfield, Missouri, handling more than two million calls a year and recognized three times as Contact Center of the Year. Their agents are 100% university-educated, recruited and coached specifically for consumer sales conversations rather than scripted call deflection. The company reports sub-1.5% monthly attrition and a 3.5-year average tenure, which they frame as 5–10x industry retention rates. For reactivation, Gold Mountain targets dormant segments including 18-month-plus inactivity files, lapsed owner files, cancelled booking lists, and aged enquiry revival. Their process includes reason-for-lapse discovery, new destination hooks, reinstatement offers, and objection recovery. The company reports 8.14% net conversion on inbound reservation calls, roughly 70% above the outsourcing benchmark and sustained for more than two years. They hold ISO 27001, SOC 2 Type II, HIPAA, PCI-DSS, HITRUST, and GDPR certifications, making them suitable for properties with strict data security requirements.
Pros
- Specialized in hospitality and vacation ownership win-back
- University-educated sales agents with low attrition
- Strong enterprise security and compliance certifications
- Proven conversion metrics sustained over multiple years
- Scales from pilot to 100 agents in production by week 12
Cons
- Pricing not publicly disclosed
- Best suited for larger programs (pilot-to-scale model)
- Focused on vacation ownership and timeshare, may be overkill for smaller resort properties
- Human agent model rather than AI-assisted calling
Best for: Vacation ownership properties and resorts with large lapsed owner databases seeking a fully managed sales team with proven conversion metrics and enterprise-grade security certifications
#5 Olivia (by Pete & Gabi) — Contact for pricing
Olivia is an AI sales agent developed by Pete & Gabi, built specifically to bring back lost customers, reduce churn, and recover revenue from dormant accounts. According to their website, Olivia handles high-volume outbound calling, qualifies intent in real time, updates CRMs, and escalates hot conversations directly to sales teams. The company positions Olivia as a plug-and-play solution that integrates easily with existing CRMs and starts generating revenue within days. Olivia's strength lies in its ability to adapt to objections, assess customer sentiment, and offer personalized win-back incentives in real time. The AI-powered outbound calling operates at scale, with personalized customer re-engagement based on history and behavior, real-time intent qualification, and objection handling. This makes it a robust solution for properties looking to boost occupancy and revenue by reconnecting with past guests who haven't booked in extended periods. For resort and all-inclusive properties, Olivia's value proposition centers on recovering revenue from dormant guest accounts that manual outreach never has time to reach. The platform captures consent and is described as highly compliance-ready. However, Olivia is voice-first with limited visual chat capability, and best results require clean escalation rules to route hot leads effectively. The company acknowledges that reported limitations exist in handling complex win-back scenarios that may require human intervention.
Pros
- Built specifically for customer reactivation and revenue recovery
- Handles high-volume reactivation without quality degradation
- Fast deployment with revenue generation within days
- Clear, measurable ROI tied to recovered deals
- Captures consent and is highly compliance-ready
Cons
- Voice-first approach with limited visual chat capability
- Best results require clean escalation rules
- Reported limitations in handling complex win-back scenarios
- Less suited for properties needing deep hospitality-specific customization
Best for: Resort and all-inclusive properties seeking AI-powered outbound calling to reconnect with former guests and boost occupancy and revenue without adding staff
Reactivating dormant guests is one of the highest-ROI activities a resort or all-inclusive property can run in 2026. The leads were already paid for once, and reaching back to them costs a fraction of new acquisition while converting at substantially higher rates. The providers above represent different approaches to this challenge: managed AI calling with strict list discipline, human agent teams with decades of hospitality experience, inbound reservation conversion specialists, and AI sales agents built for reactivation at scale. If your priority is a fully managed, compliance-forward service that runs structured win-back campaigns against your approved guest lists without requiring you to build internal call center capacity, My AI Call Center stands out for its list discipline, transparent pricing, and commitment to reporting only actual outcomes. The first campaign review is free, and the full cost is known before you approve launch. Reach out at [email protected] or visit myaicallcenter.app to plan your reactivation campaign.
Frequently asked questions
What makes My AI Call Center different from other win-back call providers?
My AI Call Center operates as a done-for-you managed service rather than self-serve software. You buy campaigns that their team runs end-to-end, with one clear goal per campaign quoted before launch. The company enforces strict list discipline: only approved, permissioned, or reviewed contact lists are accepted, and bought lists without clear consent records are flagged or declined. This protects resort properties from TCPA risk while ensuring campaigns reach guests who actually want to hear from you. Outcomes are reported honestly with no invented metrics, and pricing starts at 9¢ per connected minute with the rate locked for the campaign.
Why is list discipline important for resort reactivation campaigns?
Resort guest databases often contain contacts with unclear opt-in status: past guests who booked through third-party channels, inquiry forms from years ago, and loyalty members who haven't engaged in extended periods. Calling these contacts without proper consent documentation can expose your property to TCPA violations, which carry statutory damages of $500–$1,500 per call. Providers with strict list discipline, like My AI Call Center, review list source and consent records before any campaign launches and decline lists that cannot support the campaign, protecting your brand and budget.
How long should a resort wait before re-engaging a dormant guest?
Industry benchmarks suggest that guests who haven't booked in 30–60 days are still highly reachable, with reactivation rates of 20–30%. At 3–6 months, reactivation drops to 8–15%. Beyond 12 months, conversion falls to 2–6% but can still be worthwhile for high-lifetime-value guests. My AI Call Center's Win-Back & Reactivation campaign typically targets 12–24 month dormants, the segment where a structured, personalized call can reopen a relationship that email and SMS cannot.
What compliance considerations apply to AI-powered resort calling?
AI-generated voices are treated as artificial voices under the TCPA, requiring prior express consent before calling. State-specific quiet hours, day-of-week restrictions, and registration rules vary by jurisdiction and must be honored. AI disclosure must be made on every call, and recipients must be able to request a human, ask if the call is AI-assisted, or opt out. Keyword opt-outs like STOP and REVOKE must be honored immediately and carried into client DNC records. My AI Call Center applies all of these standards by default and notes that clients remain responsible for obtaining appropriate legal guidance before launch.
How much does a win-back calling campaign typically cost?
Costs vary significantly by provider and campaign structure. My AI Call Center charges 9¢ per connected minute as a starting rate, tiered by volume, plus a one-time campaign setup and flat monthly management fee quoted before launch. Human agent call centers like OnBrand24 and Gold Mountain by Hugo require custom quotes based on campaign scope. Performance-based services like Winback Engine charge $1,000 for a 30-day pilot plus a percentage of recovered revenue. The first campaign review with My AI Call Center is free, so you know the full investment before approving launch.
Can win-back campaigns integrate with our existing CRM and booking system?
Yes. My AI Call Center routes outcomes, bookings, and follow-up requests directly into the CRM and scheduling tools you already run. Hot leads can transfer to your team live or land in your CRM with full disposition codes (confirmed, qualified, renewed, opted out, no answer). This means your reservations and marketing teams work re-engaged guests rather than chasing cold lists, and your database stays current with every campaign.
What results can we expect from a resort reactivation campaign?
Industry benchmarks for service business reactivation put average rates at 10–15%, with best-in-class programs hitting 25–40% when using trained agents and tight segmentation. For resorts specifically, the economics favor reactivation strongly: acquiring a new guest can cost 5–7x more than reactivating a past guest, and a reactivated guest often returns with higher average booking value. My AI Call Center commits to reporting only actual outcomes, with dispositioned contact lists, outcome counts, and routed follow-ups, so you can measure true reactivation impact rather than vanity metrics.