How Microsoft is building a journey-centered operating model across customer success and experience

Raymond Otero, Director of Global Customer Experience at Microsoft, joins Jochem van der Veer for a milestone 50th episode to explore how customer success and customer experience are converging into a unified, journey-based operating model. With nearly three decades of experience across multiple industries, Raymond offers a compelling vision for how organizations can move beyond silos to create true customer value—and why AI will fundamentally reshape these roles in the years ahead.

Here’s why you don’t want to miss this episode

Journey as the universal glue

Raymond advocates for using customer journeys as the connective tissue across all organizational silos. Rather than viewing CX as surveys and contact centers or CS as post-sales support, he demonstrates how a journey-based approach aligns sales, customer success, product, and experience teams around shared customer outcomes.

Leaning left: Pre-sales involvement transforms success

Customer success teams at Microsoft are "leaning left" into the sales process, getting involved early when opportunities enter the CRM. This blurred line between sales and success enables teams to plan proactively, leverage CX data before deals close, and create smoother transitions for customers.

The joint operating model

Drawing from his experience building practices from scratch, Raymond details his methodology for creating joint operating models with customers. These frameworks map out specific milestones, assign clear accountability across internal teams, and invite customers into co-creation rather than transactional relationships—all without mentioning product names until implementation.

AI as role evolution, not elimination

While acknowledging AI will automate tactical work like ticket management and report generation, Raymond sees this as an opportunity for customer success professionals to evolve into strategic coaches. The industrial revolution analogy holds: roles won't disappear, they'll transform into higher-value functions focused on business outcomes and thought leadership.

Culture shift over metrics

Before choosing OKRs or KPIs, organizations need executive alignment and a fundamental culture shift. Raymond emphasizes keeping success metrics simple (two to three maximum) and focusing on business value delivery rather than vanity metrics like CSAT scores that don't correlate with revenue.

The Future Is Journey-Based

This episode offers a pragmatic blueprint for CX and CS leaders navigating organizational transformation. Raymond's emphasis on journey alignment, early cross-functional involvement, and strategic coaching over tactical execution provides a clear path forward as AI reshapes customer-facing roles. His message is ultimately optimistic: by removing silos and focusing on shared customer journeys, organizations can create the "kumbaya moment" where teams work together seamlessly.

For leaders looking to bridge the gap between customer experience and customer success—or anyone curious about how Microsoft approaches journey-based transformation at scale—this conversation is essential listening.

If you want to hear the entire conversation, watch the podcast with Raymond and Jochem on The Experience Edge.

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