THE LEADERSHIP DINNER SERIES

BEYOND PERSONALIZATION: HOW AI POWERS ANTICIPATORY SERVICE

In today’s AI conversation, the focus often centers on efficiency, automation, and cost reduction. But in luxury hospitality, where every detail, emotion, and personal connection matters, the greatest opportunity may be something far more powerful: using AI to help each guest feel more deeply known.

The Ritz-Carlton Yacht Collection is approaching AI through this distinctly customer-first lens. Rather than using technology simply to streamline interactions or replace human touchpoints, the organization is leveraging AI to uncover richer insights, recognize individual preferences, and empower employees to create experiences that feel thoughtful, personal, and highly considered.

In this keynote, Julio Lopez, Vice President of Sales Enablement, Global Reservations, will share how his team is using AI to better understand guest personas, identify motivations, and expectations earlier in the customer journey, and equip advisors with the intelligence needed to deliver the anticipatory service that defines the The Ritz-Carlton Yacht Collection.

TURNING SUPPORT INTO STRATEGY: ZILLOW’S APPROACH TO SMARTER SELF-SERVICE

When customers can’t find answers, they don’t just get frustrated — they lose trust in your brand. For Zillow Group, that risk was hiding in plain sight: numerous separate help sites, four technology platforms, and twelve support silos, each inherited through years of acquisitions. On paper, the support infrastructure existed. In practice, it looked like Zillow’s org chart — not its customers’ journeys.

In this keynote, Phoebe Schultz, Vice President of Customer Experience Operations at Zillow Group, shares how a fragmented support ecosystem became the unlikely catalyst for one of the most consequential CX transformations in the company’s history. What started as a consolidation project became a fundamental rethinking of what a help experience can be — not a cost center to minimize, but a product to design, a friction detector to mine, and a precision router to get the right customer to the right human at exactly the right moment.

Join this session to discover:

• The Org Chart Trap: Why most support experiences are built inside-out — and the strategic cost of designing for internal convenience instead of customer clarity.
• Help as a Product: How Zillow applied product discipline to its support infrastructure, building a unified experience where human teams are supercharged by AI and can serve millions of consumers and tens of thousands of real estate professionals from a single intelligent destination.
• Friction as Signal: How a unified platform transforms your help site from a static library into a real-time indicator of where your products, your communications, and your processes are failing your customers — before the complaints reach your contact center.
• Human Where It Matters: The framework for building intelligent triage that scales digital self-service without sacrificing the human moments that build lasting loyalty — and how to know the difference.

Green Metrics, Red Flags: Redefining Trust in the Era of AI

On paper, the dashboards look perfect. CSAT is strong, operationally, the marks are being hit, and the metrics are green. Yet across the industry, leaders are waking up to a challenging reality: a profound disconnect often exists between what the data says and what customers actually experience.

In this keynote, Julie Weingardt, Chief Operations Officer at Turo, explores the critical tipping point where traditional “Satisfaction” breaks down and “Trust” becomes the true currency of customer loyalty. It highlights the reality that a meaningful share of consumers now bypass traditional feedback channels entirely and go directly to social media when trust breaks. Ultimately, this session serves as a vital framework for the modern CX leader navigating the push for AI cost-efficiencies while preserving the indispensable value of human empathy, speed, and context.

Join this session to discover:

• The Danger of “Dashboard Blindness”: How to align organizational transparency with customer reality when green metrics mask underlying friction.
• Reading Between the Data Lines: Why “unrated” interactions don’t mean “neutral,” and how hidden gaps in automation and data silently impact the bottom line.
• The New Leadership Blueprint: Shifting from reactive satisfaction to proactive advocacy by rethinking how organizations listen, measure, and scale authentic loyalty.
• The Cost-Trust Paradox: Strategic guardrails for evaluating the AI vs. human agent mix, and the essential frameworks required to measure true effectiveness without bankrupting customer trust.

Mental Athlete: Leadership in a Dysregulated World

What if the leadership principles and attributes that built your career are now liabilities? What if your instincts, once indispensable, quietly hold your team back? What if your strategies are shaping outcomes in unseen ways?

With three decades of operational leadership, and difficult chapters in his own personal journey, Todd argues the next frontier isn’t just operational; it’s internal. As AI transforms roles overnight, teams aren’t just adapting; they’re questioning value and future. What they need most isn’t a strategy deck, it’s a steady leader. A dysregulated leader cannot calm a dysregulated team.

The cost of getting this wrong is real: high performers leave without telling you why, fear-based decisions replace clear thinking, and morale decays invisibly — until it collapses.  The separation between an effective leader and a destructive one isn’t whether they carry anger, pain, or pressure.  It’s whether they make their people pay for it.

Join Todd as he explains why the Mental Athlete isn’t the one who pushes hardest.  It’s the one who knows themselves well enough to lead from clarity rather than fear and creates the kind of safety where others can do the same. Come ready to look inward and lead differently because of it.

The Rise of Multimodal Customer Experience: Are We Moving Too Fast?

Omnichannel was promised as the solution to a fragmented customer journey. While it delivered in many ways a new paradigm is taking shape, one defined by multimodal experiences powered by AI, automation, and real-time context.

Customers can now move fluidly between voice, chat, video, and digital channels, often without a visible transition. For some, this represents the ideal journey. For others, it can feel as though the human element of customer care is slipping away.

As organizations race to innovate, many are unintentionally creating gaps, not just between channels, but between themselves and key segments of their customer base. With varying levels of digital fluency and generational differences, and varying expectations, a one-size-fits-all approach to CX no longer scales.

So, the question becomes: In our pursuit of the future, are we leaving parts of our customer base behind?

In this candid and forward-looking discussion, CX leaders will explore:

• What moving beyond omnichannel really looks like in a live environment
• How to make shifts in channel strategy without alienating customers
• Identifying where AI and automation enhance the journey and where they risk creating friction
• How generational and behavioral differences are reshaping modern channel strategy
• Signs that your organization may be prioritizing technology at the expense of connection
• How to design experiences that balance innovation with inclusivity and trust

CX Livewire: Consumer Voices, Real-Time Reactions

Customer expectations are constantly evolving, and understanding how consumers perceive service, support channels, and emerging technologies is critical for shaping effective CX strategies. In this fast-paced and interactive session, panelists will explore key insights from Execs In The Know’s latest research findings, capturing the perspectives and expectations of CX leaders and consumers.

Throughout the discussion, panelists will react to both the research findings and live polling of the CRS audience, creating a dynamic comparison between what consumers say they want and how organizations are currently approaching service delivery. These real-time insights will allow attendees to benchmark their own thinking against the room, while panelists share practical perspectives from inside their organizations on how they interpret, and respond to, shifting consumer expectations.

Expect candid reactions, engaging audience participation, and thought-provoking contrasts between consumer sentiment and operational reality. This high-energy session is designed to spark conversation, challenge assumptions, and highlight where CX leaders may need to adapt in order to meet the evolving demands of their customers.

Agent-Facing AI for CX: Through the Eyes of the Agent

For decades, contact center agents have been expected to act as human search engines navigating complex knowledge bases, policy documents, and fragmented systems to find the right answer for customers. But the emergence of agent-facing AI is beginning to shift that paradigm. Instead of simply retrieving information, modern AI tools can now interpret context, surface relevant guidance, and recommend next-best actions in real time.

This panel will explore how CX leaders are deploying AI to transform the agent role, and what this experience is like from the agent’s perspective. Panelists will discuss how tools such as AI copilots, real-time knowledge synthesis, contextual assistance, automated summarization, and predictive assistance are helping agents navigate complex conversations more effectively while reducing cognitive load. At the same time, organizations must carefully balance automation with human judgment, ensuring agents remain empowered decision-makers.

Panelists will also address the operational and cultural challenges of introducing AI into the agent workflow including trust, training, governance, and change management. Attendees will hear practical insights (and hopefully firsthand feedback from agents) on what’s working, what’s not, and how agent-facing AI can simultaneously improve efficiency, enhance employee experience, and deliver better outcomes for customers.

The Next Gen CX Business Plan: Preparing for the Next 3–5 Years

For years, organizations have piloted AI-powered support, automation, proactive service models, and intelligent self-service. Now, the industry is reaching an inflection point: what happens when these capabilities mature into the standard operating model?

The question for leaders is no longer if these technologies work, but how to architect a business plan that thrives once they are fully integrated. Moving from pilot to scale requires a fundamental shift in how we lead. It demands a roadmap for workforce evolution, a commitment to data integrity, and a new definition of “success” that balances efficiency with the human connection customer still crave.

What does workforce strategy look like when AI handles a significant portion of interactions? How do roles evolve? What investments must be made now in data quality, governance, and systems integration to support intelligent, proactive service? How is success measured? How do organizations deliver the trust, clarity, and the confidence that define Customer Assurance?

In this discussion, CX leaders will explore:

• How organizations might evolve their business plans as AI, automation, and proactive service shift from experimentation to core operations
• Redefining roles and team structures as AI handles a larger share of the interaction volume
• Aligning funding priorities and performance measures to reflect the reality of a proactive, next-generation environment
• Ensuring clarity, confidence, and human connection remain the foundation of the customer experience as technology becomes more embedded

Customer Assurance: A Leadership Decision, Not a Department

Customer Assurance is not a department or a checklist. It is the confidence customers feel when they know a company will show up with clarity, competence, and care. It is built through leadership decisions that shape how the organization communicates, operates, and responds when something matters most.

In an era defined by automation, AI, and no-reply emails, customers are tired of simply being processed. They are asking deeper questions: Do I feel safe doing business with you? Do I trust this experience? Do I believe this company will take care of me when it counts?

True assurance is what turns a transaction into trust. It requires more than strong service design. It takes leadership alignment, clear decision-making, and systems that make confidence possible at every stage of the customer journey. That includes how expectations are set, how issues are owned, how employees are empowered, and how technology is used to support rather than distance the customer relationship.

In this discussion, CX leaders will explore:

• The leadership pillars that help build Customer Assurance across the organization
• The systems, processes, and policies that reinforce customer confidence rather than undermine it
• The measures and signals that show whether customers actually feel trust, clarity, and confidence
• How honesty, transparency, and accountability are becoming stronger differentiators in customer relationships
• How AI, automation, and digital tools can either strengthen assurance or erode it, depending on how they are deployed