Our IT Executive Roundtables are invite-only events hosted by peers for peers that bring together a select group of senior IT leaders from across industries for topic-driven, intimate dialog on current trends and topics. The group met remotely to discuss creating a platform for scalable, connected experiences led by the SVP of Technology of a global health and fitness subscription technology company. This Session was sponsored by Twilio.
As organizations strive to meet increasing customer expectations and operational demands, modernizing the core has become a strategic necessity. However, modernization today entails more than just upgrading infrastructure—it involves establishing a flexible foundation that fosters connected experiences, contextual engagement, and ongoing innovation.
In this Executive Roundtable, technology leaders from various industries convened to discuss how modernization strategies are adapting to the needs for scalability, agility, and AI integration. Through open discussions and shared challenges, participants provided valuable insights into what it genuinely means to develop a platform capable of supporting long-term transformation.
Modernization is increasingly being reframed not as a destination but as a capability. Across industries, organizations are moving away from lengthy, rigid transformation programs in favor of modular strategies that prioritize continuous improvement. Rather than aiming for a comprehensive overhaul, leaders are building core systems that support rapid iteration and adjustment. This shift reflects a broader recognition that evolving market conditions, rising digital expectations, and the accelerating pace of technological advancement require a more fluid and responsive approach.
Participants emphasized the importance of delivering incremental value as a way to gain traction and support. Small-scale pilots, when tied to tangible outcomes, allow organizations to validate ideas quickly, reduce risk, and generate momentum. Agility becomes not only a technical objective but a strategic advantage—enabling teams to pivot resources, shift roadmaps, and realign with customer and business needs as they evolve. The ability to adapt, rather than merely implement, is now seen as a core capability for future readiness.
Underpinning this mindset is a recognition that flexibility must be built into both systems and culture. Traditional models of transformation—centered on fixed, multi-year initiatives—no longer align with how organizations operate today. Instead, adaptability is emerging as the central organizing principle. From project-to-product thinking to agile development practices, organizations are reshaping how they measure success—not by how complete a transformation is, but by how ready they are to handle what comes next.
A consistent theme throughout the discussion was that data fragmentation remains one of the greatest barriers to modernization. Many organizations have matured to the point where they are generating vast quantities of valuable data across customer touchpoints, operations, and internal systems. However, this data is often siloed, inconsistently defined, or locked away in legacy infrastructure. As a result, it cannot be leveraged effectively to power real-time insights, contextual experiences, or scalable AI use cases.
To overcome this challenge, enterprises are increasingly prioritizing unified data architectures. Some are developing common data layers or data fabrics that aggregate and harmonize inputs from across departments. These foundational frameworks enable organizations to move away from point-to-point integrations and toward a composable architecture—one where data flows freely, supports observability, and enables system-wide orchestration. The benefits are not only technical; unified data empowers better decision-making, operational alignment, and end-to-end visibility.
This shift toward data unification is not a luxury—it's becoming a prerequisite. Connected experiences, intelligent automation, and AI-driven personalization all rely on consistent, high-quality data. Whether the end user is a consumer, partner, or internal stakeholder, delivering relevance and responsiveness depends on shared context. Without a common foundation, enterprises risk offering fragmented experiences that erode trust and limit scalability.
The evolution of customer expectations has outpaced the ability of many systems to respond in kind. Today’s users expect organizations to recognize them across every channel and touchpoint, regardless of where or how they engage. Delivering on this expectation means much more than omnichannel capability—it requires true contextual continuity. Organizations must not only integrate their channels but also preserve and act on the user’s history, intent, and preferences throughout the journey.
This is especially complex in industries with multilayered engagement models. Whether navigating between sales agents and digital portals or shifting from online support to in-person service, users expect a consistent and coherent experience. To meet this demand, enterprises are implementing strategies such as journey mapping by user intent, contextual API frameworks, and channel-specific design rules. These approaches aim to reduce friction, align internal teams around common outcomes, and respond to users in real time with the right information.
A connected experience also requires coordination across internal systems and data sources. If one system knows something about a customer that another does not, the continuity is broken. Maintaining a single view of the user—even across legacy and modern stacks—enables more predictive, responsive, and personalized interactions. This alignment is not only about improving the customer journey; it also drives operational efficiency, trust, and long-term engagement.
The excitement around generative AI and intelligent automation has pushed many organizations to reassess their digital strategies. However, meaningful impact depends on implementation that is both purposeful and practical. AI initiatives are most successful when aligned with clear business outcomes—such as increasing productivity, accelerating service delivery, or reducing manual workloads. Rather than adopting AI for its own sake, enterprises are choosing to start with focused, high-impact applications and scale from there.
A critical enabler of effective AI is data readiness. Many participants highlighted the importance of preparing systems for AI by investing in data quality, context, and accessibility. Without this foundation, even the most advanced models will struggle to produce relevant or trustworthy results. AI does not replace the need for solid architecture; it amplifies both its strengths and its gaps. As such, modernization and AI adoption must move in lockstep, with composable systems and governance frameworks supporting safe experimentation and enterprise-wide integration.
Beyond performance, AI is also changing the expectations users have for enterprise systems. The natural language interfaces and intelligent assistants used in personal life are setting a new standard for usability and support. Enterprises must now meet those expectations while preserving privacy, accuracy, and brand integrity. This means ensuring that AI systems are secure, explainable, and properly governed—a challenge that spans technology, ethics, and regulation.
Poll results from the roundtable highlighted technology leaders' focus on modernization, emphasizing foundational capabilities for adaptability and personalization. The top priority—building a flexible, future-ready platform (60%)—indicates a shift toward architectural agility as a strategic goal. Close behind is unifying customer data (50%), underscoring the importance of data consistency for connected experiences and AI innovation. These priorities show enterprises aim for immediate efficiencies while preparing for scalable, intelligent transformation.
Although advanced use cases like automating customer support with AI (30%) and creating seamless omnichannel journeys (30%) received attention, they were seen as secondary to the necessary infrastructure. Only 20% prioritized integrating front- and back-office systems, despite acknowledgment of its role in responsiveness and speed. This response distribution reveals a shared understanding: sustainable modernization must begin with harmonizing core platforms and data layers to deliver intuitive, scalable, and proactive customer experiences in today’s market.
The roundtable reinforced that successful modernization is not about reaching a final state—it’s about enabling resilience, responsiveness, and relevance. Whether through composable architectures, intelligent data fabrics, or AI-powered workflows, organizations are building ecosystems that can grow and evolve alongside shifting needs. The most effective strategies are those rooted in clear business outcomes, where every technological advancement supports improved experience, operational efficiency, or strategic differentiation.
Ultimately, the path to scalable, connected experiences starts with a unified vision of what modernization should enable: consistent data, contextual engagement, and the agility to move at the speed of change. As these conversations continue, the insights shared in this session provide both a benchmark and a roadmap for enterprise leaders shaping the future of digital transformation.
Are you interested in furthering these discussions and contributing to more conversations on trending topics? Reach out today about joining our next Executive Roundtable.