Executive CX Leaders Virtual Roundtable

From Pilot to Production: What it Takes to Make AI Work in CX

THURSDAY, MAY 21, 2026

1:00 pm - 2:00 pm ET

Most CX teams have run an AI pilot. Far fewer have turned one into something that consistently performs — at scale, across real workflows, without eroding the experience their brand is known for.

The pressure to move fast is real. So is the cost of getting it wrong. Forrester estimates a third of companies will erode customer trust by deploying AI prematurely. The difference between teams that are seeing results and those that aren't isn't access to technology. It's the decisions made in design, deployment, and ongoing operation.

In this roundtable, we'll dig into what's actually working and what isn't. Which use cases are delivering measurable value? What had to change operationally to get there? And what does it look like to scale AI beyond basic automation into the interactions that really define your brand?

Meghan Knoll, Chief Experience Officer at BARK, will share how her team approached this challenge firsthand — extending the quality of a deeply human CX operation to handle growing volume, without sacrificing the care their customers expect.

Drawing on patterns Sierra sees across enterprise deployments, we'll explore how leading teams are approaching workflow design, continuous improvement, and the evolving role of CX professionals as AI takes on more of the work.

This is a practitioner conversation — focused on what it takes to go from early adoption to consistent, scalable impact.

Key Takeaways:

  • Where AI is delivering measurable value in CX today

  • The operational decisions that separate successful deployments from stalled pilots

  • How to maintain brand quality and trust as you scale

  • How CX team roles are evolving — and how to bring your people along

  • What success looks like beyond containment rates

Who Should Attend

Strategic CX Leadership: Senior leaders (Director level and above) responsible for setting CX vision, owning enterprise-wide CX strategy, and driving measurable business outcomes.

Operational & Transformation Owners: Leaders who oversee customer care, service, or support operations and are accountable for improving processes, technology, and team performance.

Peer-Driven Problem Solvers: CX executives seeking candid, real-world conversations with peers to share insights, challenges, and best practices across industries.

 

Why Attend

Peer-to-Peer Insights: Senior CX leaders seeking candid discussions with peers facing similar challenges and opportunities.

Networking with Industry Leaders: Expand your professional network and build connections with senior CX executives across sectors.

Real-World Problem Solving: Share experiences, explore best practices, and gain actionable strategies to improve customer experience outcomes.

Stay Ahead of Trends: Hear diverse perspectives on emerging CX trends, technologies, and operational strategies shaping the industry.

Interactive, Collaborative Format: Participate in an intimate, discussion-driven setting designed for meaningful conversation rather than one-way presentations.

As our guest, you’ll receive a digital package that includes the attendee roster prior to the event, along with a post-event executive summary and curated discussion highlights. 

This experience is intentionally not recorded, and we encourage you to attend live to fully engage in the conversation.

Meet your Hosts & Speakers

Hosted by:

Chad McDaniel
Co-Founder and President

Partner Speakers:

MEGHAN KNOLL, CHIEF EXPERIENCE OFFICER
 
Meghan Knoll is the chief experience officer at BARK, where she ensures that both dogs and their humans have exceptional product, delivery, customer service and digital experiences. Meghan rejoined BARK in June 2024 after a detour into the feline world as CEO of Cat Person, a subscription-based cat food company backed by Harry’s Labs. Prior to that, she spent seven years at BARK in roles ranging from head of labs to SVP of Direct to Consumer. Earlier in her career, she oversaw digital product development for Nick Jr. at Viacom—so she’s no stranger to keeping both pets and kids entertained. When she’s not obsessing over customer retention, Meghan can be found playing with her two dogs, Tonks and Fozzie Bear, who likely believe they should be running the company.

ANDREW KIM, HEAD OF AGENT DEPLOYMENT

Andrew Kim leads Agent Deployment at Sierra, where he helps enterprises bring conversational AI agents into production. He works at the intersection of AI, product, and customer experience, with a focus on how companies move beyond experimentation and apply AI to real business challenges. Previously, Andrew was Chief Operating Officer at Hopin and StreamYard, and held leadership roles at Cisco and Accompany across product, operations, and go-to-market.