CSS Executive Forum Raleigh (RTP): Where Customer Leaders Are Building the AI-Enabled Future
# CSS Executive Forums
An Afternoon of Insight, Innovation & Peer Connection
October 20, 2025
Omid Razavi
Last week, Red Hat opened its doors at City Center in Raleigh for an exceptional gathering of Customer leaders from across the region and beyond. Nearly a year since our last reunion, the return of the CSS Executive Forum was filled with fresh ideas, lively debates, and an undeniable sense of community. The event once again felt less like a conference and more like a reunion of innovators, comparing notes from the frontlines of digital transformation and AI-driven change.
The energy across the spaces was grounded yet forward-looking, from the interactive roundtable workshops in the afternoon to the evening forum and networking sessions that carried well into the night. Leaders weren’t just networking; they were problem-solving together—sharing lessons from pilot purgatory, debating build-versus-buy strategies, and exchanging insights on what’s truly driving business value versus what only looks good on slides.
Our partners Foresight, Kore.ai, and Gainsight led engaging sessions that sparked some of the day’s most insightful discussions on operationalizing customer value realization, activating agentic AI for CX advantage, and mastering proactive customer health through data and automation. Their workshops offered practical, experience-based perspectives on the complex challenges that many of us are navigating today.
It was an event defined by openness, collaboration, and curiosity—a reminder that the future of AI in customer organizations isn’t being built in isolation but together, through communities like this one in Raleigh (RTP)
Roundtable Summary: Foresight – Operationalizing Customer Value Realization at Scale
Nigel Hammond (Co-Founder and CEO) and Sagar Shukla (Co-Founder and COO) of Foresight, joined by Cyrus Gerami, Head of Business Value for the Americas at Red Hat, led an insightful discussion on how revenue and retention leaders can use AI to quantify customer outcomes and proactively drive retention and growth.
They explored how post-sales organizations can bridge the gap between executive vision and operational execution by mapping customer outcomes, use cases, and product features to measurable business value. Sagar shared the story of Bandwidth, a Raleigh-based customer, illustrating how Foresight’s value framework unifies Product, Customer Success, and Sales around a shared language of outcomes. Cyrus described how Red Hat scaled its business-value practice globally by embedding value conversations throughout the customer lifecycle.
The key takeaway: Customer value realization is the foundation of retention, growth, and long-term trust—and AI is making it measurable at scale.
Roundtable Summary: Kore.ai – Activating Agentic AI for CX Advantage
Cathal McCarthy, Chief Customer Officer, and Abby Gamble, Senior Director of Customer Success at Kore.ai, guided participants through a practical discussion on moving from experimentation to execution in the adoption of AI.
They emphasized that successful organizations treat digital agents as part of the workforce, with defined roles, responsibilities, and decision authority. Cathal introduced a structured framework for thinking about AI agents as systems that observe, plan, reason, and act, urging leaders to tie each use case to clear KPIs to avoid “bubbles of automation.” Drawing from enterprise examples like Citibank, he illustrated how hybrid models—where humans and AI work together—deliver superior results.
The session’s message resonated deeply: success with AI is not about flashy demos, but about building a coordinated digital workforce that augments people, scales intelligently, and drives measurable outcomes.
Roundtable Summary: Gainsight – Mastering Proactive Customer Health with AI
Josh Schachter, Senior Vice President of Strategy & Market Development, and Ben DeFoe, Regional Vice President of Enterprise Sales at Gainsight, led an engaging discussion on how AI is reshaping customer health management in an increasingly competitive environment.
They observed that traditional SaaS moats are eroding as customers gain the ability to build their own solutions, making retention more strategic than ever. The conversation centered on three pillars for success with agentic AI: start with trusted data, ensure clear and documented processes before automating, and maintain a sharp focus on outcomes and ROI.
Real-world examples showed how AI enables CSMs to expand coverage and reduce prep time while focusing on higher-value activities. With Gainsight’s acquisition of Staircase AI, the company now delivers real-time, omnichannel intelligence that detects risk, surfaces expansion opportunities, and strengthens relationships. The key takeaway: to scale customer health and growth, teams must pair structured data and process discipline with AI-driven insight.
Presentation Summary: Red Hat – Scaling Support with AI and Human Collaboration
Scott Froehlich, Vice President of Global Customer Support at Red Hat, shared insights from the company’s two-year journey to integrate AI into support operations.
The journey began with a focus on efficiency and automation but soon revealed that data readiness—not tools—is the foundation for success. Once Red Hat invested in cleaning, structuring, and enriching its data, AI began uncovering valuable insights about product performance, associate skills, and customer behavior.
Scott detailed how Red Hat uses smaller, cost-efficient AI models to balance accuracy and performance and how collaborative “AI sprints” between engineers and support teams are driving innovation. The company’s Ask Red Hat initiative—an intelligent front door for customer inquiries—has transformed both internal workflows and customer experience.
Scott’s closing message was clear: the goal is not full automation but intelligent collaboration between people and AI. “Jobs will change,” he noted, “but they’ll become more complex, solution-oriented, and customer-centric—and that’s where AI helps us raise the bar.”
Keynote Summary: Bain & Company – Making AI Real: From Pilots to Performance
Matt Eldridge, Partner at Bain & Company, shared new research on how Customer Success organizations can move beyond AI experimentation to measurable impact.
While IT and CS investment remain steady in 2025, Net Revenue Retention (NRR) has fallen 10 points since 2020, even as CS headcount has grown 42% and the number of CCOs has tripled. Bain’s survey found that most organizations are stuck in early AI maturity and have yet to scale pilots effectively.
Matt outlined four imperatives to break free from “pilot purgatory”:
- Set a bold, top-down AI objective tied to coverage or CX.
- Focus on two to three high-impact processes for transformation.
- Redesign workflows with AI in mind.
- Invest in change management to drive adoption.
The north star, he emphasized, is to double CSMs’ customer-facing time and elevate CS from a cost center to a strategic growth driver.
Panel Summary: Leading Through AI, Value Pressure, and Changing Customer Expectations
Moderator: Jay Nathan, CEO of Balboa Solutions
Panelists: Toya Del Valle (former CCO, Cornerstone), Annette Sanders (SAS), Andrew Cromey (former SVP, TSIA)
The closing panel explored how organizations are leading through shifting market pressures, rising customer expectations, and the accelerating pace of AI adoption. Profitability and retention have become top priorities, with AI serving as a critical enabler to scale engagement and efficiency.
Panelists discussed the convergence of Customer Success, Support, and Services as customers increasingly seek outcomes, not handoffs. They also addressed the need for new hybrid roles that combine consultative and AI-augmented skills. Adoption, they agreed, requires both cultural and operational transformation—balancing experimentation with governance, training, and clear ROI.
Key takeaways:
- Anchor AI initiatives to profitability and retention goals with measurable KPIs.
- Start with clear objectives and focus on high-impact processes.
- Redesign workflows for AI instead of layering tools onto legacy systems.
- Build skills around data literacy, value communication, and human-AI collaboration.
- Move toward unified, outcome-based customer experiences across post-sales functions.
A Thriving CSS Community in Raleigh (RTP)
The Customer Service, Support, and Success (CSS) community in Raleigh (RTP) continues to shine as one of the most vibrant, forward-thinking ecosystems in the country. The conversations and collaborations at this forum reflected the region’s unique blend of innovation, authenticity, and leadership.
Thank you to everyone who participated—our speakers, partners, and attendees—for contributing to a day filled with insight, inspiration, and connection. Your engagement and openness made the event truly special. We look forward to continuing the dialogue, forging new partnerships, and shaping the future of Customer Success and Support together in the months ahead.
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