Raymond Otero

I am a seasoned executive with over 27 years of experience in driving cloud adoption, customer success, and digital transformation for enterprise clients across various industries, including financial services, manufacturing, healthcare, life sciences, and the federal sector. My career has been dedicated to aligning cloud solutions with business objectives to deliver measurable outcomes and competitive advantages.

Throughout my career, I have successfully managed Fortune 500 accounts, expanded multi-year customer portfolios, and led C-suite engagements to accelerate cloud innovation and revenue growth. My strategic approach has consistently resulted in significant year-over-year growth and enhanced customer satisfaction.

At Microsoft, I have held pivotal roles, including Director of Global Customer Experience and Senior Principal Customer Success Director. In these positions, I have led global customer experience strategies, orchestrated cross-cloud consumption plans, and fostered executive sponsorships to drive strategic account plans. My leadership has been instrumental in achieving over 115% attainment year-over-year and improving account and team performance.

Prior to Microsoft, I held leadership roles at Amazon Web Services, Comport Consulting Solutions, and Anexinet Consulting, where I pioneered cloud technology strategies, optimized cloud operations, and drove account growth through strategic planning and process improvement.

I am passionate about leveraging advanced analytics and AI-driven solutions to redefine cloud engagement models and enhance customer solutions. My ability to mentor teams, develop strategic partnerships, and implement innovative customer-centric initiatives has been recognized through various awards and nominations, including being a Global Ambassador and Content Leader for the Customer Success Collective Organization.

With a strong foundation in executive stakeholder engagement, cross-functional collaboration, and strategic sales planning, I am committed to driving digital transformation and customer success at the highest levels. I am now seeking new leadership opportunities where I can continue to make a significant impact and contribute to the success of forward-thinking organizations.

I am a strategic cloud transformation leader and USAF veteran with over 27 years of experience in driving digital evolution for organizations. Combining deep technical expertise with proven customer success methodologies, I deliver tailored cloud solutions that achieve measurable business outcomes and ensure seamless adoption. My collaborative approach and track record of leading high-impact teams make me the ideal partner for maximizing cloud investments and accelerating digital transformation.

Microsoft Corporation

Director, Global Customer Experience - Strategic Programs (May 2024 - Present)

• I lead and orchestrate strategic initiatives that significantly enhance the customer experience worldwide.
• I foster a culture of innovation within my team, encouraging creative problem-solving and proactive thinking.
• I implement journey-based transformations that embed customer journeys into operating models, creating a cohesive and impactful customer journey.
• I develop customer empathy and improve products based on customer feedback.

Senior Principal, Customer Success Director (Oct 2021 - May 2024)

• I led strategic account management for Fortune 500 clients, driving multi-year growth strategies and cross-cloud adoption plans.
• I partnered with system integrators and account executives to expand revenue streams and strengthen customer relationships.
• I orchestrated cross-cloud consumption plans and managed global success & support teams.
• I cultivated C-level relationships to drive customer success, influencing strategic roadmap decisions and securing long-term commitments to Microsoft's cloud solutions.

Amazon Web Services Inc

Global Customer Solutions Sr. Mgt. - FSI (Jan 2018 - Oct 2021)

• I led cloud transformation initiatives for enterprise accounts, establishing Centers of Excellence to optimize cloud operations, increase cost efficiency, and maximize customer ROI.
• I owned the cloud adoption methodology and identified opportunities for enhancement.
• I drove account growth through opportunity identification and process improvement.
• I redefined cloud engagement models aligning with market demands.
• I provided thought leadership on emerging trends within AWS.

Comport Consulting Solutions

Vice President, Cloud & Emerging Technologies (Jan 2017 - Aug 2018)

• I pioneered cloud technology strategies, enhancing service offerings and market position.
• I analyzed market trends to align tech developments with business goals, optimizing ROI.
• I boosted regional sales by leading strategic vendor negotiations and team development.
• I oversaw business development in Northeast and Mid-Atlantic regions.
• I innovatively developed emerging technology strategies.

Anexinet Consulting / Verinext

Sr. Mgr., End-User Computing & Infrastructure (Jan 2013 - Jan 2017)

• I analyzed data from market research to identify trends and develop actionable insights for organizational growth.
• I monitored competitor activities to anticipate changes in the industry landscape and design appropriate response measures.
• I coordinated with internal departments to ensure successful execution of projects according to timeline and budget constraints.
• I managed an end-user computing practice team, focusing on operational, sales, and partner management.
• I generated revenues and provided sales and presales enablement on EUC products.

Education

• Cornell University: Master Certificates in Executive Leadership & Financial Management
• Capella University: Master of Science in Information Technology
• University of Phoenix: Bachelor of Science in Information Technology
• Community College of the Air Force: Associate of Applied Science in General Studies

Awards and Recognitions

• I received various Org Team Awards for prioritizing key focus areas, achieving greater transparency, alignment, and collaboration, and enhancing security and scalability.
• I was recognized as a Global Ambassador & Content Leader by the Customer Success Collective Organization.
• I was a Global Customer Success Leader of the Year Finalist 2024.
• I was named Customer Success Leader to Watch for 2025.
• I was nominated as a Customer Success Innovate Lead by the Microsoft Worldwide Customer Success Leadership Team.

Cornell University: Master Certificates in Executive Leadership & Financial Management

• Focused on developing leadership skills and financial acumen to drive strategic initiatives and manage organizational finances effectively.

Capella University: Master of Science in Information Technology

• Specialized in advanced IT concepts, including cloud computing, cybersecurity, and data management, to support digital transformation and technology-driven business solutions.

University of Phoenix: Bachelor of Science in Information Technology

• Provided a strong foundation in IT principles, including network infrastructure, software development, and systems analysis, to support various technology roles.

Community College of the Air Force: Associate of Applied Science in General Studies

• Combined general education with technical training, enhancing skills in communication, critical thinking, and technical disciplines relevant to IT and management.

Certifications

• CCA XenApp Administration
• MCTS - Windows Server 2008 Network Infrastructure, Configuring
• Amazon Web Services Business Professional
• VMSP - Veeam Sales Professional
• Amazon Web Services Cloud Practitioner

Languages

• English: Native or Bilingual
• Spanish: Native or Bilingual
• Yiddish: Professional Working
• Italian: Elementary
• German: Limited Working
• Hebrew: Limited Working

Honors and Awards

• USAF Honorable Discharge
• USAF Achievement Medal
• Global War on Terrorism Expeditionary Medal
• National Defense Service Medal
• GFS Customer Obsession Award