Gladly Connect Live 2025

6-9 PM The Country Music Hall of Fame and Museum.

What does it take to be the best? The individuals and teams who achieve at the highest levels have one thing in common: they push the envelope and go to the edge of their boundaries. As a combat-tested fighter pilot and a member of the military’s most elite group of aviators (1 in 2,000 USAF pilots become Thunderbird pilots), Col Nicole Malachowski will share actionable lessons from a distinguished 21-year career — inspiring the courage to push the envelope in your life. That means learning to trust in your teammates’ skill and precision, while developing your own, being mindful of the over-control that leads to performance malfunctions, and preparing for turbulence, because change is unrelenting, but you must anticipate it. Nicole’s presentation provides an unforgettable and practical roadmap for organizations looking to achieve great things together at a time of unprecedented change.

Col. Nicole Malachowski

USAF (Ret.)

The days of customer service being "just" a cost center are over. In this candid fireside chat, Kate Showalter, Vice President of CX Services at Crate and Barrel, reveals how she's fundamentally reimagining customer service for 2025 and beyond. She'll share how her team is moving beyond traditional metrics to become an essential driver of company strategy and growth. Learn how they're breaking down organizational silos to create true customer centricity, turning service interactions into revenue opportunities, and leveraging AI to drive innovation – all while building fierce customer advocacy backed by data. Join us for an unfiltered conversation about what it really takes to transform customer service from a necessary expense into an indispensable strategic advantage.

Kate Showalter

Vice President, CBH Services, Crate and Barrel

Charlie Besecker

President, Gladly

Move beyond metrics to master the art of executive influence. Drawing from her experience advising growth-stage companies and scaling customer experience organizations, Mara Castro reveals proven frameworks for transforming service initiatives into compelling C-suite narratives. Learn how to translate metrics into business impact stories and create ROI models that resonate with senior leadership.

Mara Castro

COO, Twentyeight Health

It’s time to turn your customer support organization into a revenue generation machine. Join Ben Devey, Senior Director of Customer Experience at Ollie, and Jim Rodden, Chief People Officer at MaryRuth's, as they share how they used AI to transform their support organizations into a revenue generators and give you the tools to do the same. In this session, you'll learn how to develop a revenue-focused strategy, leverage AI to identify upsell and cross-sell opportunities and personalize recommendations, and empower your agents to create revenue generation moments, as well as measure and track your success.

Ben Devey

Senior Director of Customer Experience, Ollie

Jim Rodden

Chief People Officer, MaryRuth’s

When BSN Sports faced the challenge of modernizing their customer service operations, Director of CX Mandi Geary knew getting team buy-in would be crucial. Learn how their creative "lonely robot adoption" program turned potential AI anxiety into excitement. See how BSN empowers their agents to confidently handle a 32,000-product catalog through a harmonious blend of AI assistance and human expertise. Walk away with practical strategies for bringing your technology and team into perfect harmony.

Mandi Geary

Director of CX, BSN Sports

Join Lauren Inman-Semerau as she walks through the practical steps of planning, training, and growing your AI program from initial goal-setting through measuring success. Learn how thoughtful setup enables measurement, how treating AI as a new team member rather than just a tool is key to Rothy’s approach, and how using AI implementation can be an opportunity to develop your customer service team’s careers as well as a cost savings journey. You'll leave with a playbook on how to implement an AI program that drives efficiency while maintaining quality, including real examples of how Rothy's achieved consistent SLAs and managed peak seasons without additional hiring.

Lauren Inman-Semerau

Head of Customer Experience, Rothy's

Join Tim Wickes, Director of Customer Service at Tecovas, to learn how seamless platform integration can transform your customer support. In this session, you’ll discover how Tecovas connected Gladly with their existing systems to give agents and AI instant access to customer data and context, resulting in faster support, more personalized interactions, more revenue, and happier customers. Tim will walk you through their approach, share key metrics, and offer actionable insights you can apply to your own customer service strategy. Walk away with a clear understanding of how to boost agent efficiency, increase customer satisfaction, and deliver a more connected, consistent customer experience.

Tim Wickes

Director of Customer Service, Tecovas

When your whole company embraces customer service as their mission, magic happens. Join this candid conversation about breaking down silos between IT and service teams to create seamless, technology-powered customer experiences that truly deliver. Learn practical strategies for reducing IT friction, implementing new tools and technologies, and creating a company-wide mandate in all departments of building a culture centered around excellent customer service.

John Burke

VP of Customer Experience & Technology, Wine Enthusiast

Explore how two distinctive brands are reimagining white glove service for today's customer. Learn how they're strategically using AI to handle routine tasks, freeing up their teams to deliver the personalized, high-touch experiences that build lasting customer relationships and ensure revenue generation. Discover practical strategies for elevating your service experience while maintaining efficiency.

Hailey Ellsworth

Director, Customer Experience, Framebridge

Nancy Orgill

Customer Support Manager, Kuhl

There are few customer service experiences that are higher pressure than supporting customers for an airline. Danny will walk you through how he and his team created an empathetic AI in both design — how it works and handles agent transitions — and communication — the language it uses to communicate to customers. In addition, this session will focus on crisis management, and how Danny’s team prepares for potential adverse situations with their AI technology.

Danny Cox

Vice President of Guest Experience, Breeze Airways

You might not like your current customer support platform, but you know that it’s not easy to make the switch. Why haven't you moved? What are you afraid of? What would the work actually be? In this session, customer support technology consultant Kelsey Nash, who has implemented Gladly at numerous companies in multiple industries, will reveal a step-by-step playbook that will make switching to Gladly easy.

Kelsey Nash

Customer Service Technology Consultant

StockX isn't just serving the next generation - they're reinventing service for them. Join Andy Lisk to understand how StockX uses AI to approach customer service for a generation that expects immediacy, authenticity, and seamless experiences. Learn how they've built a service organization that speaks Gen Z's language while maintaining the trust and verification that their marketplace demands.

Andy Lisk

Vice President, Global Head of Customer Service, StockX

Winning companies place quality at the center of their employee and customer experience - it's what separates them from the rest of the pack. Customers expect a feeling of quality in every interaction, from the product to the support they receive. Every business, no matter the product, industry, or geography, can create a quality-first mindset that fuels extraordinary customer experiences. This session will show you how to operationalize a quality-first mindset across all departments, from customer support to product development - provide real-world examples of companies that have made this transformation and share the classic signs of cultures where quality is words but not action. You’ll gain actionable takeaways into building a lasting competitive advantage by committing to quality in your business.

Vasu Prathipati

CEO, MaestroQA

Thomas Harden

Sr. Director of Customer Care, The Black Tux

Brian Kershon

Director of Customer Experience, Zenni Optical

Event Hall at The Country Music Hall of Fame

As we celebrate our 10-year anniversary, Gladly's CEO, Joseph Ansanelli, will reflect on our journey, highlight transformative product development, and inspire Gladly Connect Live attendees with a bold vision for the future of customer service.

Joseph Ansanelli

CEO, Gladly

This 60-minute master class brings together CX leaders from Nordstrom, Warby Parker, Catalyst Brands, and Crate & Barrel to share how they're navigating revenue generation, service innovation, and AI implementation in today's rapidly evolving retail landscape. Get an unfiltered look at how they're handling shifting channel preferences, meeting evolving customer expectations, and creating extraordinary experiences that drive growth. Whether you're reimagining your digital strategy, expanding service channels, or transforming customer care into a competitive advantage, you'll walk away with actionable insights from some of retail's most innovative brands.

Heather Bissell

Interim VP, Customer CARE & Fraud, Nordstrom

Christina Sheehan

Associate Director, Workforce Analytics and VOC for Customer Care, Crate and Barrel

Sara Autry

Head of Customer Experience, Warby Parker

Jay Breuer

Senior Director, Customer Care, Catalyst Brands