In an increasingly complex travel landscape, artificial intelligence (AI) agents are emerging as a pivotal technology for airlines and other travel companies to forge deeper, more enduring connections with their customers. By meticulously retaining context and intelligently acting upon dynamic signals throughout the entire customer journey, these sophisticated AI systems have the potential to elevate isolated customer service interactions into a consistent and powerful engine for fostering loyalty, driving direct bookings, and ultimately, maximizing revenue. A comprehensive Skift Research survey, encompassing nearly 7,000 global travelers, underscores the evolving and multifaceted nature of the path to purchase in the travel industry. The discovery phase, once a relatively straightforward process, now spans an intricate web of search engines, social media platforms, and burgeoning AI-powered tools. Significantly, over 60% of travelers who are aware of AI are already leveraging its capabilities to assist in their trip planning endeavors. However, the actual booking process, while influenced by this discovery phase, remains more concentrated on a select few channels where critical factors such as competitive pricing, unwavering trust, and flexible payment options reign supreme. For airlines, the fundamental challenge lies in effectively bridging the gap and maintaining a cohesive customer relationship across this fragmented journey. A single traveler might interact with the same carrier across numerous touchpoints – from initial inspiration on social media to booking through a third-party site, and subsequent service inquiries. This creates a pressing need to connect these disparate experiences in a more meaningful and impactful way over time. While customer-facing AI agents have already demonstrated their prowess in enhancing individual service moments – whether it’s answering routine inquiries, facilitating reservation changes, or efficiently resolving customer issues – the next frontier lies in extending this value proposition by carrying crucial context from one conversation to the next. Airlines’ customer experience, loyalty, and digital leadership teams are now tasked with a critical strategic decision: how will AI agents be integrated and orchestrated across functions that have historically operated in distinct silos? As these agents are increasingly empowered to handle complex scenarios such as disruption recovery, proactive rebooking, upgrade opportunities, and comprehensive loyalty program support, a unified approach to customer context becomes paramount. Failing to establish this shared understanding of customer information now risks entrenching disconnected systems, which will only become more challenging and costly to untangle in the future. Erik Zahnlecker, agent product manager at Sierra, a company at the forefront of AI agent development, elaborates on the transformative potential of these advanced systems. "Long-running AI agents are designed to stay with both the customer and the task over time," he states. "This kind of continuity can connect planning, booking, service, loyalty, and the months between trips into a more persistent customer relationship." This "long-running" capability is a game-changer, moving beyond transactional interactions to build enduring connections. Building Continuity Across the Travel Journey Zahnlecker aptly describes the current travel discovery landscape as a series of discrete, one-way touchpoints. Travelers might consume information from a website, scroll through a social media feed, compare options across online travel agencies (OTAs), and then move on to another platform, often without a seamless thread connecting these activities. AI agents, however, possess the remarkable ability to transform these isolated touchpoints into ongoing, dynamic conversations. They can seamlessly pick up where a traveler left off in their planning process or proactively engage when a relevant signal emerges, demonstrating a keen understanding of the traveler’s evolving needs and interests. "Fundamental to that is memory and context," Zahnlecker emphasizes. "What do you know about the customer? What do you remember from prior interactions? That’s what allows you to move from a conversation to a lasting relationship." This emphasis on memory and context is the bedrock upon which persistent customer relationships are built. Without it, AI interactions remain superficial and transactional, failing to foster the depth of engagement required for true loyalty. The reality of travel planning and execution is that it rarely unfolds in a single, uninterrupted sitting. The planning phase can stretch over days or even weeks, with significant periods of time elapsing between booking a trip and the actual departure. Furthermore, there are often extended intervals between subsequent travel experiences. An AI agent that is equipped to retain relevant context can meticulously remember a traveler’s preferences, seamlessly resume a previous conversation, and continue to work diligently towards achieving a desired outcome. This continuity not only alleviates the frustration of travelers having to repeatedly provide the same information but also empowers the agent to anticipate future needs, proactively reach out at opportune moments, and maintain consistent progress towards the traveler’s goals over an extended period. The ideal customer experience, as envisioned by Zahnlecker, also transcends single channels. "The most advanced version has agents working across multiple channels, including chat, email, SMS, and voice," he notes. Imagine a scenario where a traveler is engaged in a phone conversation with an AI agent but needs to transition to another task. The agent can seamlessly offer to continue the conversation via text message, allowing the traveler to pick up precisely where they left off, demonstrating an unparalleled level of flexibility and customer-centricity. From Flight Disruption to the Next Best Action Flight disruptions, a perennial challenge for the airline industry, represent one of the clearest and most impactful test cases for the application of long-running AI agents. These events have an immediate and significant effect on both passenger experience and an airline’s profitability. When weather events or operational issues ground flights, passengers are often left to navigate a complex and stressful situation, independently trying to understand what happened, searching for alternative flight options, and contacting overloaded customer service centers. A long-running AI agent, however, can proactively act upon the disruption signal, initiating contact with affected passengers before customer service queues even begin to form. Once initiated, the agent can then meticulously weigh each traveler’s unique priorities against the airline’s operational rules and available inventory in real-time. This personalized approach is crucial; one passenger might urgently need to reach their destination for a critical family event, while another may have greater flexibility. Similarly, one traveler might insist on remaining in business class, while another is willing to consider an economy seat to reach their destination sooner. "The agent can navigate both the traveler’s needs and the airline’s rules to find the best available flight and ultimately get them where they need to go," explains Zahnlecker. This intelligent prioritization and optimization capability not only resolves immediate travel needs but also enhances the customer’s perception of the airline’s care and efficiency during a stressful event. The agent’s role does not necessarily conclude once a passenger has been successfully rebooked. If the disruption leads to an eligible compensation claim, the agent can seamlessly carry the relevant context and documentation into the reimbursement process, streamlining what is often a cumbersome administrative task. If a traveler’s preferred seat remains unavailable, the agent can continue to monitor inventory and proactively re-engage the passenger when their desired seat becomes available. Crucially, a disruption handled as a single, continuous journey – encompassing rebooking, expense management, and even future loyalty considerations – rather than a series of disjointed and frustrating interactions across disparate systems, can be the deciding factor in whether the airline recovers the customer relationship or loses them permanently. The Revenue Opportunity Starts Before the Next Booking The extended period between travel experiences represents one of the most significant underutilized assets in the customer relationship lifecycle for many airlines. This inter-trip window is often dominated by generic marketing emails, leaving airlines with minimal meaningful engagement with their travelers until the next promotional campaign is launched. Zahnlecker posits that this period is a natural and highly opportune use case for Sierra’s Horizon agents. These agents are capable of responding to subtle yet significant signals, such as a recently completed trip, an upcoming travel anniversary, a detected fare drop to a previously explored destination, or even an event that aligns with a traveler’s known interests. "The more personalized the interaction, the more likely someone is to engage and see the agent as a trusted concierge," Zahnlecker asserts. This personalized approach moves beyond generic marketing to offer genuine value and assistance, fostering a sense of partnership with the traveler. This can effectively surface latent demand that might otherwise remain dormant, leading to direct bookings, valuable ancillary purchases, or even inspiring entirely new travel plans that the customer had not yet begun to consider. Independent research from Skift Research, specifically focusing on destination loyalty and the race to capture the repeat traveler, further illuminates the immense value of the post-trip engagement window. This research highlights the 30 days immediately following a trip as a particularly critical period for sustained engagement. A striking 52% of surveyed travelers indicated that personalized recommendations for a future visit would be highly beneficial. This data underscores a significant missed opportunity for airlines that are not actively engaging customers in this prime window. The question for airline leaders is no longer if this opportunity exists, but rather, how much of it has remained untapped due to the historical difficulty of engaging customers at scale in a personalized and meaningful way. Personalization Changes the Economics of the Offer Beyond simply re-engaging customers, AI agents possess the capability to fundamentally shape and optimize the offers presented to travelers during the crucial period between booking and departure. This intelligent shaping of offers can encompass a wide range of ancillary services, from seat and cabin upgrades to baggage allowances, in-flight Wi-Fi, premium dining options, or even bundled rental car services. Loyalty can be woven into the fabric of these interactions, providing the agent with invaluable context to determine the optimal moment to present an offer and, crucially, which specific offer is most likely to resonate with and be accepted by the individual traveler. Zahnlecker explains that offers can increasingly be dynamically shaped by a confluence of rich customer data and the analysis of previous interaction outcomes. For instance, one traveler might demonstrate a higher propensity to accept a cabin upgrade offer, while another might be a stronger candidate for loyalty program enrollment or a different type of ancillary purchase. The cumulative commercial impact of such personalized and context-aware offers can be substantial. Higher conversion rates on ancillary sales, stronger attachment of additional services, and a significant increase in repeat business all contribute directly to enhanced customer lifetime value. Even modest improvements across these key metrics can translate into considerable financial gains when scaled across an entire customer base. An adjacent example from the broader travel industry illustrates the tangible commercial impact of this approach. A prominent travel platform has successfully deployed a Sierra agent across its web and mobile interfaces to assist members in clarifying plan benefits, exploring alternative options, and identifying overlooked value. According to Sierra, this AI agent has been instrumental in achieving a 5% increase in plan retention while simultaneously maintaining an impressive customer satisfaction score of 4.7. While this specific use case centers on membership benefits rather than airline ancillaries, it powerfully demonstrates how more relevant, context-aware interactions can simultaneously bolster the customer experience and drive favorable commercial outcomes. Staying Relevant Without Becoming Noise The success of persistent engagement hinges entirely on its perceived usefulness by the traveler. An AI agent that reaches out at an inappropriate or irrelevant time risks quickly devolving into another form of marketing noise, easily ignored or even actively avoided by the recipient. True relevance is achieved through a sophisticated synthesis of signals emanating from various enterprise systems, such as customer relationship management (CRM) platforms or airline reservation systems (PSS), combined with the deep learning derived from ongoing conversational interactions. For example, if a traveler expresses that premium economy seating is a significant preference, but no such seats are currently available, the agent can internally "remember" this preference and proactively monitor inventory for future availability, rather than repeatedly querying the traveler about the same unmet need. "Over time, those conversations can build a richer customer profile that the agent can act on," Zahnlecker observes. This continuously enriched customer profile, when combined with real-time signals such as the availability of new inventory or a personalized event notification, can create what he aptly terms "a reasonable moment to reach out." These moments are characterized by their timeliness, relevance, and inherent value to the traveler, ensuring that the AI’s engagement is welcomed rather than intrusive. Leaders Across Travel Face the Same Decision While airlines present a particularly visible and high-stakes scenario for the application of these advanced AI capabilities, the underlying challenge is rapidly emerging across the entire travel ecosystem. Hotel groups, for instance, face the intricate task of seamlessly connecting reservation management, loyalty programs, pre-arrival offers, on-property service delivery, and post-stay engagement. OTAs are increasingly leveraging AI agents to manage complex processes like refunds, cancellations, and check-ins. Similarly, cruise lines are discovering significant opportunities to enhance customer interactions across booking, onboard revenue generation, and post-cruise re-engagement initiatives. Across all these diverse sectors, a common theme emerges as AI agents take on a more expansive role in orchestrating the customer journey. Their inherent ability to share and leverage context across both service-oriented and commercially driven moments will increasingly become a defining factor in shaping both the overall customer experience and the tangible value they deliver to the business. Start Small, Then Expand the Relationship At their full potential, AI agents can provide comprehensive support to travelers across every stage of their journey, from the initial spark of discovery and the booking process through to on-trip service and meaningful post-trip engagement. However, Zahnlecker wisely recommends a phased, iterative approach to building towards this ambitious vision. A travel company might strategically commence with a high-volume yet contained use case, such as managing reservation confirmations, cancellations, or modifications. Alternatively, an organization could introduce an AI agent to a small, controlled segment of its customer traffic or initiate deployment on a single channel, such as chat or voice, before systematically expanding its reach. "Focus on a few use cases that are maybe not your most critical, but where there’s enough volume to learn quickly, build trust, and improve the experience," Zahnlecker advises. "Then scale from there." Embarking on this journey with a smaller, focused scope does not negate the necessity of a holistic, cross-functional strategic vision. Teams must cultivate a shared understanding of the agent’s intended purpose, the crucial context it needs to retain and leverage, and the key business outcomes it is designed to achieve. The window of opportunity for making these foundational decisions is rapidly narrowing as AI agents increasingly transition into customer-facing and commercially significant roles. Travel suppliers that proactively establish the right architectural and strategic foundation now will be exceptionally well-positioned to scale these transformative capabilities over time and, critically, to capture incremental revenue from each and every customer relationship. Post navigation Navigating the Crowded Horizon: A Biannual Best-Of in a Transformative Travel Year
