As enterprises race to automate customer interactions and optimize operational efficiency, a growing challenge has emerged across industries: how to preserve emotional connection while scaling digital experiences. Organizations are increasingly realizing that customer loyalty is no longer sustained purely through transactional rewards, pricing advantages, or frictionless interfaces. Instead, differentiation is being driven by trust, consistency, personalization, and the ability to create memorable human-centered experiences across every touchpoint.
This challenge becomes even more complex in multi-stakeholder ecosystems such as hospitality, travel, commerce marketplaces, and platform businesses where customer expectations continue to rise while operational pressures intensify. The leaders shaping the future of CX are therefore those capable of balancing automation with empathy, efficiency with service culture, and digital innovation with authentic human engagement.
About Lisa Checchio
Lisa Checchio brings a uniquely cross-industry perspective to customer experience leadership. Currently serving as Chief Commercial Officer at Entertainment Benefits Group, Lisa has spent her career leading large-scale customer, loyalty, and commercial transformation initiatives across hospitality, aviation, travel, and commerce ecosystems.
Prior to EBG, Lisa held senior leadership roles at Wyndham Hotels & Resorts and JetBlue Airways, where she helped shape customer engagement, loyalty innovation, brand strategy, and experience transformation initiatives serving millions of consumers globally.
What distinguishes Lisa’s leadership philosophy is her emphasis on bringing a hospitality mindset into every industry — viewing customer service not as a support function, but as a long-term strategic growth engine capable of driving loyalty, differentiation, and emotional brand affinity.
Interview Introduction
Customer experience strategy is entering a defining phase where businesses are under simultaneous pressure to automate operations, reduce costs, increase personalization, and sustain emotional connection with customers. While technology continues to accelerate digital convenience, many organizations are discovering that efficiency alone is no longer sufficient to create durable loyalty or meaningful differentiation.
In this CXQuest.com leadership interview, we speak with Lisa Checchio, Chief Commercial Officer at Entertainment Benefits Group, about the evolving relationship between hospitality, customer loyalty, AI, and experience strategy. Drawing from leadership roles across hospitality, aviation, and commerce ecosystems, Lisa shares why service culture remains a competitive advantage even in increasingly automated environments.
The conversation explores the future of loyalty, the operational realities of multi-stakeholder platform businesses, frontline empowerment, and the importance of preserving humanity within digital transformation efforts.
Hospitality, Aviation, and Platform Commerce
Q1. You’ve led customer and commercial transformation initiatives across hospitality, aviation, and now platform commerce. What core customer experience principles remain universally relevant across industries?
LC: Whether someone is walking into a stadium, boarding a flight, checking into a hotel, or booking an experience online, they are trusting us with their time, money, and something that matters to them. The setting changes; the need to feel welcomed and valued does not. The principle that holds true in every one of those settings is hospitality, and hospitality starts with serving the customer. That means making their choice feel right: keeping the experience simple, being clear about our promises, and following through. I also look beyond the transaction. A completed purchase tells us the process worked. A customer who wants to come back—and recommends us to others—tells us much more about the experience.
Q2. Many organizations today are aggressively pursuing automation and efficiency. Where do you believe automation reaches its limits in customer experience delivery?
LC: I am all for making things easier. Nobody should have to call to resolve something they could quickly handle online themselves. But when someone wants to speak with a person, that should be simple, too. Automation reaches its limit when customers have to adapt to the system instead of the system responding to their needs. My test is not simply whether automation reduces calls or messages. It is whether customers reach the right outcome with less effort. A shorter interaction does not necessarily mean the issue is resolved or the customer is satisfied.
Hospitality Mindset Into Every Industry
Q3. You often emphasize bringing a hospitality mindset into every industry. What does that philosophy practically look like inside organizations that are not traditionally hospitality-driven?
LC: To me, hospitality is how you make people feel, not an industry. We talk a lot about customer service, but the word that matters most is serving. In practice, I ask: Did we welcome someone, respect their time, and help them feel confident in their decision? On a digital platform, that might mean explaining an offer clearly, taking out unnecessary steps, or making help easy to find. A design choice or purchase policy can communicate care just as powerfully as a conversation. You do not need a hotel lobby to practice hospitality. You need the intention to take care of the person on the other side of the interaction.
Q4. Loyalty programs across industries are evolving rapidly. How do you define loyalty today beyond traditional rewards structures and transactional engagement?
LC: I define loyalty as confidence in a relationship—the feeling that choosing a brand again is a decision you can trust. It goes beyond what customers buy to what they remember and what they tell others. A recommendation is especially meaningful to me: people put their own credibility behind a brand when they encourage someone else to choose it. That is loyalty expressed through action.
Biggest Misconceptions
Q5. What are the biggest misconceptions organizations still have about customer loyalty and retention?
LC: The biggest misconception is equating repeat purchases with loyalty. Price, promotions, and convenience can bring someone back without creating a lasting relationship. I believe loyalty programs work best when they make that relationship more rewarding and easier to understand; they cannot replace it. If an incentive is the only reason to return, a better offer elsewhere can change the decision. I want to understand what matters beyond the offer: Do customers trust us, feel appreciated, and believe we will help when something goes wrong? That is what gives a loyalty program lasting meaning.
Emotional Connection at Scale
Q6. Can companies build emotional connections at scale in highly digital environments? What does it take to deliver that consistently?
LC: Yes, but I do not think every digital interaction needs to feel like a personal conversation. Sometimes care is a clear confirmation, a useful reminder, or getting help without having to repeat your story. It can also mean tailoring communications to previous behavior or preferences a customer has chosen to share. When someone chooses to tell us more about themselves, we should show we were listening—not by sending more messages, but by making them more relevant. To deliver that consistently, teams need the right customer information, the ability to act on it, and dependable service behind every promise. The emotional connection comes from a simple conclusion: this company understands what I need and makes my life easier. Technology can support that feeling, but the business has to deliver it.
Frontline Employees
Q7. Frontline employees remain central to customer perception despite growing digital adoption. How should organizations rethink frontline empowerment in modern CX ecosystems?
LC: To me, empowerment means giving people the information, training, and authority to help, with clear boundaries and a straightforward way to bring in additional support when needed. I think of the frontline employee as the CEO of that interaction: equipped to take ownership and solve problems in the moment. Customers want help, not to be passed from person to person, and people who choose service roles should feel able to serve. As routine needs move online, the conversations that reach a person may require more judgment. We need to prepare teams for that, rather than measure every interaction like a simple transaction. Empowerment also means listening to what they learn. A recurring customer question is not just a service issue; it is valuable feedback for the teams designing the experience.
Role of Organizational Culture
Q8. What role does organizational culture play in delivering consistent customer experiences across large distributed operations?
LC: I see culture as the foundation of consistency. A brand promise may be defined at the top, but people deliver it through everyday decisions across locations, teams, and partners. Everyone needs to understand what that promise means in their work, whether they answer customer questions or build the checkout experience. Hospitality starts inside the organization. How we share information, take responsibility, and solve problems together shapes the care customers receive. Culture matters most when there is no script for the situation in front of you.
Q9. How can companies maintain brand consistency while still allowing frontline teams the flexibility to personalize experiences?
LC: I distinguish consistency from uniformity. Customers should receive the same honesty, clarity, and commitment to helping them—not an identical response regardless of their circumstances. I believe in clear non-negotiables: what we promise, what we can deliver, and where the boundaries are. Within those boundaries, people need room to respond to the individual. One customer wants a quick answer; another needs help exploring the options. Both can receive an experience that feels true to the brand. Good standards give people confidence to exercise judgment, not a script that replaces it.
Unique CX Challenges
Q10. EBG operates within a complex multi-merchant and member-based ecosystem. What are the unique CX challenges that emerge in platform business models?
LC: For 25 years, EBG has connected the people using our marketplaces, the organizations providing access, and the partners supplying products and experiences. Each has different needs, but customers should not have to navigate that complexity. The challenge is making every stage clear: what an offer includes, how the purchase works, what happens next, and where to get help. Completing a purchase and enjoying the experience are distinct moments. I see our role as helping connect them while respecting each partner’s responsibilities. The complexity belongs behind the scenes, not with the customer.
Q11. How do you orchestrate seamless experiences across digital and physical touchpoints without creating fragmentation for customers?
LC: I start with the customer’s goal, not how they interact with us. Someone buying a ticket is thinking about enjoying the event, not where one company’s digital experience ends and another’s begins. The transitions—confirmation, delivery, redemption, arrival, and support—deserve particular attention. Are the instructions clear? Is the information consistent? Is help easy to find? The priority is to review those transitions with the teams and partners involved, looking for missing information and unnecessary effort. One company does not need to manage every step. What matters is that information and support carry through from one stage to the next.
Siloed Ownership of Customer Journeys
Q12. Many organizations struggle with siloed ownership of customer journeys. What governance or operational structures have you found most effective in aligning experience delivery?
LC: I favor a shared definition of success and clarity about who is responsible for delivering it. A customer journey may involve marketing, product, technology, operations, service, and partners. Every team can meet its own targets while the customer still has a disconnected experience. The key is to bring those teams together, look at the journey from the customer’s perspective, see where things get difficult, and agree on who will lead the work to resolve those issues. The goal is not another committee. It is better decisions across teams, so customers never have to navigate our internal structure to get help. We also have to listen to what customers are telling us. We may think we have created a great experience, but if they are telling us something different, that matters more.
Q13. AI is transforming how organizations engage customers. Where do you see the greatest opportunities for AI to improve experience quality rather than simply reduce operational cost?
LC: What interests me most is AI’s potential to help customers and employees reach better answers. That could mean making choices easier to navigate, helping service teams find relevant information, or revealing recurring sources of confusion. For me, the priority is better understanding and service, not simply more interactions. I would ask: Is the information accurate? Is it useful? Does it help meet the customer’s need? If we save time internally but create uncertainty for customers, we have improved the wrong thing.
Overly Transactional Engagement Models
Q14. How should organizations approach personalization without crossing into intrusive or overly transactional engagement models?
LC: My starting point is usefulness: does personalization help customers do something they want to do, or simply give us another reason to market to them? Good personalization cuts out irrelevant options, makes communication more timely, and remembers preferences people have chosen to share. It should never leave someone wondering how much a company knows about them or why it is making assumptions. Avoiding that means asking permission, giving people clear choices about what they share, and using that information with restraint. Done well, personalization feels like thoughtful service. When it feels like pressure or like being watched, it undermines the trust it is meant to build.
Q15. What safeguards should companies consider as AI-driven experiences become more embedded into customer journeys?
LC: I would start with clear responsibility. A person or team must remain responsible for what happens to the customer, even when AI supports the interaction. I would also prioritize protecting customer information, testing for inaccurate or inappropriate responses, and setting clear limits on what a system can decide or promise. Pricing, availability, eligibility, and cancellation terms require dependable sources—not answers that simply sound right. Customers should know when they are interacting with AI and have a practical way to reach a person. Innovation should earn trust through reliability, not ask customers to overlook its limitations.
Your Leadership Journey
Q16. Looking back across your leadership journey, what customer experience decisions or initiatives had the most lasting organizational impact?
LC: The decisions that stand out to me are the ones that bring what we promise customers closer to what we actually deliver. That means treating simplicity as a business priority, not just a communications goal, and connecting customer experience, product, and operations to the broader strategy. Across my career, I have seen how closely brand, service, and commercial decisions are linked. A compelling message may bring someone in; the experience determines what happens next. The lasting lesson is that customer experience cannot be a separate effort. It has to shape how the business works, so the brand promise becomes something customers can experience and trust.
Q17. What leadership lessons have become more important in today’s environment of rising customer expectations and operational uncertainty?
LC: Presence has become even more important to me: giving the moment—and the person in front of me—my full attention. It is hard to listen well when you are already thinking about the next meeting. Curiosity matters just as much: staying open to learning, asking questions, and challenging the way things have always been done. I do not believe leaders need every answer, but we do need clear priorities, honest communication, and a willingness to listen to customers and colleagues. I also believe in getting a little better each day. Progress does not always require a major breakthrough; small improvements add up. Optimism matters, too—not as a way to dismiss challenges, but as confidence that we can work through them. For me, leadership means staying close to people, remaining curious, and helping them see a way forward.
Truly Excel at Customer Experience
Q18. Looking ahead five years, what characteristics will define the organizations that truly excel at customer experience?
LC: I believe the strongest organizations will use technology with a clear understanding of how they want customers to feel. They will use data and AI to make things easier while being equally deliberate about openness, human support, and keeping promises. They will connect the whole journey, not just perfect individual moments. An impressive website means little if getting help afterward is difficult. The advantage will not be technology alone, but how thoughtfully it serves people. Five years from now, I believe strong customer relationships will still come down to a familiar feeling: I made the right choice, and this company values my business.
Key CX Leadership Insights
1. Hospitality Principles Are Expanding Beyond Hospitality
Organizations across industries increasingly recognize that hospitality-style service thinking — empathy, responsiveness, personalization, and emotional intelligence — can create stronger differentiation than technology alone.
2. Automation Must Strengthen, Not Replace, Human Connection
AI and automation can reduce friction and improve scalability, but sustainable loyalty still depends on trust, emotional resonance, and thoughtful human engagement during critical moments in the customer journey.
3. Loyalty Is Becoming Experience-Driven Rather Than Transaction-Driven
Customers are increasingly loyal to brands that consistently deliver clarity, convenience, personalization, and emotional reliability rather than purely rewards-based incentives.
Editorial Reflection
The most compelling insight emerging from conversations with leaders like Lisa Checchio is that customer experience leadership is becoming fundamentally more human even as technology becomes more advanced. While organizations continue investing heavily in AI, automation, predictive analytics, and operational efficiency, long-term differentiation increasingly depends on preserving emotional connection and customer trust.
This shift is particularly significant because many industries spent years optimizing primarily for speed, scale, and cost reduction. Today, however, customer expectations have evolved toward something deeper: consistency, empathy, recognition, and frictionless engagement across increasingly complex ecosystems. Businesses that fail to balance efficiency with humanity risk creating experiences that are technically optimized but emotionally forgettable.
Lisa’s perspective also highlights the growing importance of hospitality principles beyond traditional hospitality sectors. Whether in aviation, commerce platforms, financial services, healthcare, or retail, organizations are recognizing that service culture itself can become a strategic growth engine. In highly competitive markets where products and pricing are increasingly commoditized, customer experience often becomes the most sustainable differentiator.
As AI adoption accelerates, the organizations most likely to succeed may ultimately be those that use technology not merely to automate interactions, but to strengthen relationships, empower employees, and create experiences customers genuinely remember.
