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 Bio

Raymond (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.

Takeaways

• CX 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 reflections

LinkedIn

Raymond Otero

Jochem van der Veer

Websites

microsoft.com (Company)

(Personal)

(Personal)