This sponsored content was created in collaboration with a Skift partner.
A recent Skift Research survey of nearly 7,000 travelers shows the growing complexity of the path to purchase. Discovery now spans search, social media, and AI tools, with more than 60% of those aware of AI already using it to plan trips. Bookings, however, remain concentrated on fewer channels, where price, trust, and payment flexibility matter most.
For airlines, the challenge is maintaining the customer relationship across that fragmented journey. A traveler may encounter the same carrier across several touchpoints, creating a need to connect those experiences more effectively over time. Customer-facing AI agents can already improve individual service moments, from answering questions and changing reservations to resolving issues. The opportunity now is to extend that value over time by carrying context from one conversation into the next.
Airline customer experience, loyalty, and digital leaders have to decide how AI agents will work across functions that have traditionally operated separately. As agents take on disruption recovery, rebooking, upgrades, and loyalty support, airlines need a shared approach to customer context before disconnected systems become harder to unwind.
“Long-running AI agents are designed to stay with both the customer and the task over time,” said Erik Zahnlecker, agent product manager at Sierra, whose agents can retain context over days or months to resolve customer needs and drive key business outcomes or priorities. “This kind of continuity can connect planning, booking, service, loyalty, and the months between trips into a more persistent customer relationship.”
Building Continuity Across the Travel Journey
Zahnlecker describes today’s travel discovery landscape as a series of one-way touchpoints. Travelers read a webpage, scroll a social feed, compare OTAs, then continue elsewhere. AI agents can turn those touchpoints into ongoing conversations, picking up where the traveler left off or proactively reaching out when a relevant signal emerges.
“Fundamental to that is memory and context,” Zahnlecker said. “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.”
Travel rarely happens in a single sitting. Planning can unfold over days, with weeks or months between booking and departure, and often another long stretch between trips.
An agent that retains relevant context can remember preferences, pick up where a previous conversation left off, and continue working toward an outcome. That continuity can reduce the need for travelers to repeat themselves while also helping the agent anticipate what they may need next, proactively reach out at the right moment, and keep working toward the goal over time.
The experience can also move across channels. “The most advanced version has agents working across multiple channels, including chat, email, SMS, and voice,” Zahnlecker said. “A traveler could say, ‘I’m on the phone, but I need to go. Can you text me?’ and pick up the conversation there.”
From Flight Disruption to the Next Best Action
For airlines, disruption is one of the clearest test cases, with an immediate impact on the P&L. When a storm grounds flights, passengers often have to figure out what happened, search for alternatives, and contact the airline themselves. A long-running agent can act on the disruption signal and reach out first, before contact-center queues build.
From there, it can weigh each traveler’s priorities against the airline’s rules in real time. One passenger may need to get home for a family event, another may have flexibility, one may need to stay in business class, and another may be willing to move to economy.
“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,” Zahnlecker said.
The agent’s role does not have to end once the passenger is rebooked. If the disruption results in an eligible claim, the agent can carry the relevant context into the reimbursement process. If a preferred seat is unavailable, the agent can monitor inventory and re-engage later. A disruption handled as one continuous journey, rather than a series of disconnected interactions across rebooking, expense, and loyalty systems, can make the difference between recovering the relationship and losing the customer.
The Revenue Opportunity Starts Before the Next Booking
The stretch between trips is one of the most underused parts of the customer relationship, and one that many airlines still leave largely to marketing email. Once a trip ends, the airline may have little meaningful contact with the traveler until the next promotion.
Zahnlecker sees that period as a natural use case for Sierra’s Horizon agents, which can respond to signals such as a completed trip, an upcoming anniversary, a fare drop to a preferred destination, or an event that matches a traveler’s interests.
“The more personalized the interaction, the more likely someone is to engage and see the agent as a trusted concierge,” Zahnlecker said.
That can surface demand that might otherwise remain dormant, leading to a direct booking, an upgrade, an ancillary purchase, or even a trip the traveler had not yet started shopping for.
Separate Skift Research on destination loyalty highlights the value of the post-trip window. It identifies the 30 days after a trip as a particularly important period for engagement, with 52% of surveyed travelers saying that personalized recommendations for a future visit would be helpful.
For airline leaders, the question is how much of that between-trip opportunity has gone untapped because staying engaged at scale was difficult until now.
Personalization Changes the Economics of the Offer
Agents can also shape what happens between booking and departure by deciding which offers are most relevant to each traveler.
That could mean a seat or cabin upgrade, baggage, Wi-Fi, dining, a rental car, or another ancillary. Loyalty can sit across those moments as well, giving the agent more context for when to make an offer and which one is most likely to resonate.
Zahnlecker said offers can increasingly be shaped by customer data and previous outcomes. One traveler may be more likely to accept a cabin upgrade, while another may be a stronger candidate for loyalty enrollment or a different ancillary.
The commercial impact can add up quickly. Higher conversion, stronger ancillary attachment, and more repeat business can all contribute to customer lifetime value. Even modest gains across those areas can become meaningful at scale.
One adjacent travel example shows how that commercial impact can play out. A leading travel platform uses a Sierra agent across web and mobile to help members clarify plan benefits, explore alternatives, and identify value they may have overlooked. According to Sierra, the agent has contributed to a 5% increase in plan retention while achieving a 4.7 customer satisfaction score. While the use case centers on membership rather than airline ancillaries, it shows how more relevant, context-aware interactions can support both the customer experience and commercial outcomes.
Staying Relevant Without Becoming Noise
Persistent engagement only works if travelers find it useful. An agent that reaches out at the wrong time quickly becomes another marketing channel to ignore. Relevance depends on signals from systems such as a CRM or an airline PSS, as well as on what’s learned through conversation. If a traveler says premium economy matters but no seats are available, the agent can remember that and monitor inventory rather than asking the traveler again.
“Over time, those conversations can build a richer customer profile that the agent can act on,” Zahnlecker said. A known preference, combined with a signal such as the availability of new inventory, can create what he called “a reasonable moment to reach out.”
Leaders Across Travel Face the Same Decision
Airlines make the stakes especially visible, but the same challenge is emerging elsewhere in travel. Hotel groups need to connect reservation management, loyalty, pre-arrival offers, on-property service, and post-stay engagement. OTAs are applying agents to refunds, cancellations, and check-ins, while cruise lines have similar opportunities across booking, onboard revenue, and post-cruise re-engagement.
Across sectors, the same issue emerges as AI agents take on more of the customer journey. Their ability to share context across service and commercial moments will increasingly shape both the customer experience and the value they create.
Start Small, Then Expand the Relationship
At full scale, AI agents could support travelers across the entire journey, from discovery and booking through on-trip service and post-trip engagement. But Zahnlecker recommends building toward that vision gradually.
A travel company might begin with a high-volume but contained use case, such as reservation confirmations, cancellations, or modifications. It could also introduce an agent to a small percentage of customer traffic or start with one channel, such as chat or voice, before expanding.
“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 said. “Then scale from there.”
Starting small does not eliminate the need to think across service, loyalty, operations, technology, and revenue. Teams need a shared view of what the agent should do, what context it should carry forward, and which outcomes matter most.
The window to make those decisions is narrowing as agents move into more customer-facing and commercial roles. Travel suppliers that put the right foundation in place now will be better positioned to expand those capabilities over time and capture more incremental revenue from each customer relationship.
To learn how Sierra helps travel and hospitality companies increase bookings and loyalty with AI agents, click here.
This sponsored content was created collaboratively by Sierra and Skift Studio.