Elie Ashery on AI Agents, Humor in Support, and Listening to Understand

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Last update: December 11, 2025
Jeremy Hyde

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    CX Spotlight is a series where we speak to customer experience leaders from across industries who are rethinking support, building customer-first cultures, and finding clarity in the messiness of real-life CX.

    Every edition is a quick, candid conversation. No fluff. No jargon. Just real-world insights from people who’ve been there and done that.

    Table of Contents

    👉In Conversation With Elie Ashery

    Elie Ashery has spent over 20 years turning ideas into businesses that grow with purpose. As a founder, CEO, advisor, and coach, he has helped teams move through uncertainty, find clarity in their direction, and build products that customers rely on.

    His experience guiding companies from first version to full-scale operations earned him recognition as TEDCO’s Entrepreneur of the Year. His insights have also appeared in The Washington Post, The Wall Street Journal, and Entrepreneur Magazine.

    Today, as Co-founder and CEO of Chattitude, he’s focused on creating AI agents that handle sales, marketing, and support.

    In this edition of CX Spotlight, Elie shares how “The Fixer” mindset guides his leadership, why humor keeps customer support human, and how listening to understand strengthens the customer experience.

    1. Please tell us a bit about your job role

    As CEO, I lead the creation and growth of software that helps teams manage and automate customer experiences. The goal is to provide support that is faster, smarter, and more human.

    2. What would your support alter ego be called—and what would their superpower be?

    The Fixer. I step in when workflows get complex and bring structure back through smart automation. My focus is on creating systems that run smoothly and reliably.

    3. The weirdest or most unexpected support request you’ve ever handled?

    A customer once mentioned it was his birthday and asked me to tell him a joke. I went with one about a cookie. It was really crummy, but it made him laugh.

    4. What’s one practical change you’ve implemented to make your team more customer-centric?

    Every customer comes with specific goals and expectations. Our job is to quickly understand what matters most to them and respond in a way that delivers real value.

    5. What’s one tool or app you can’t live without at work?

    My calendar. It keeps me organized, focused, and on top of everything that matters most.

    6. One piece of advice you’d give someone who is entering the field of customer support.

    Listen to understand, not just to respond. When you approach conversations with curiosity, customers feel heard, and that’s what builds trust.

    7. What’s a use case where AI actually made things better—for either a customer or your team?

    Chattitude AI now manages tier-1 support, including FAQs, ticket triage, and scheduling. It learns from each interaction and stays aligned with our brand voice. This ensures customers get consistent, helpful responses while the team focuses on complex conversations.

    8. A book, podcast, or show you’d recommend to your peers?

    The Effortless Experience: Conquering the New Battleground for Customer Loyalty. A great read on why making things simple for customers drives loyalty faster than any surprise-and-delight tactic.

    9. If you weren’t in CX, what would you be doing?

    Teaching. I’ve always enjoyed helping people learn and grow. It’s one of the best parts of leadership, too.

    ✨Three Takeaways from Elie’s CX Playbook

    • Automation should make work easier while keeping the human touch.
    • Listening to understand creates stronger customer connections.
    • Every customer has a goal. Find it early and align your response.

    Enjoyed Elie’s take on customer experience? Connect with him on LinkedIn or check out more stories in the CX Spotlight series.

    Are you a CX leader with stories, lessons, or ideas to share? 👉 Answer these questions to get featured!

    Author

    Rashi is a B2B content marketer who helps brands strengthen customer experience (CX) and customer service (CS). She focuses on customer-first growth, creating strategies and content that drive loyalty, empower support teams, and align business goals with customer needs.

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