Ep. 50 - How Microsoft is building a journey-centered operating model across customer success and experience - Raymond Otero

Raymond Otero, Director of Global Customer Experience at Microsoft, bridges customer success and experience to create truly journey-centered transformation. With nearly three decades of experience, Ray’s approach brings operational cohesion, data-driven insights, and a cultural shift that makes customer obsession real inside the enterprise.In this conversation with TheyDo’s Jochem van der Veer, Ray unpacks how Microsoft is blending CX and CS through journey-based operating models, how AI enables proactive coaching, and why humility and alignment—not hierarchy—drive lasting success.Guest BioRaymond (Ray) Otero is Director of Global Customer Experience at Microsoft, where he leads strategic programs that connect customer success, experience design, and data insights across the organization. With over 25 years of experience spanning Citrix, Microsoft, and advisory roles with the Customer Success Collective and Influence Board, Ray helps global enterprises shift from reactive account management to proactive, journey-based transformation.TakeawaysCX and Customer Success must operate as one journey, not separate functions.“Leaning left” means involving success teams early—before the sale—to drive outcomes.AI should enhance human connection by removing repetitive tasks and surfacing insights.Journey health is the new north star—measuring alignment, not just satisfaction.True leadership requires humility, collaboration, and a culture of shared learning.Chapters 00:00 Meet Raymond Otero, Director of Global Customer Experience at Microsoft 02:00 Redefining CX and Customer Success at Microsoft 06:00 Why silos hurt the customer journey 10:00 The “lean left” principle and early success engagement 14:00 CX as data, analytics, and rhythm of business 17:00 Journey as the organizational glue 19:00 Turning journeys into joint operating models 27:00 From tactical fixes to strategic programs 31:00 How AI reshapes customer success roles 36:00 Will AI replace CS jobs? 44:00 Building better CX organizations and roles 49:00 Structuring OKRs and aligning CX metrics 55:00 Journey-centered metrics and global alignment 59:00 Creating cultural cohesion and removing silos 01:03:00 Where to find Ray and final reflectionsLinkedInRaymond Otero Jochem van der Veer Websitesmicrosoft.com (Company) (Personal) (Personal)