01
Experience
BEST BUY • SEATTLE, WA • 2023—2024
Senior Product Manager and TPM
Spearheaded a comprehensive transformation of Best Buy's membership and retention platform, architecting a unified solution that delivered exceptional results: 30% boost in member engagement and retention, near-perfect refund accuracy at 99.8%, and a 60% improvement in program quality.
By consolidating disparate member information into a single data source and reimagining customer-facing experiences, I transformed complex legacy systems into a streamlined, high-performance platform.
Through cross-functional collaboration and a relentless focus on simplification, I executed the complete vision—from strategy to tactical implementation—elevating both operational efficiency and the company's value proposition for its members.
CHEWY • BELLEVUE, WA • 2022
Staff Technical Product Manager
Led a transformative overhault of Chewy's website platform that delivered remarkable results: 50% reduction in website delay and a 60% boost in operational efficiency through strategic decommissioning of outdated endpoints.
By developing and executing a comprehensive cross-functional roadmap, I aligned short and long-term improvement strategies into a cohesive vision that significantly enhanced the end-user experience.
This careful orchestration of technical improvements and strategic planning translated directly into measurable gains in customer satisfaction while streamlining essential operations across the platform.
AMAZON • Seattle, WA • 2020—2022
Senior Technical Program Manager
Revolutionized Alexa for PC development by implementing strategic architectural improvements and quality-first practices, achieving a remarkable 70% reduction in development cycles.
Led Microsoft App Store releases while establishing innovative beta programs that accelerated feature delivery.
Championed comprehensive accessibility initiatives across five disciplines, fostering inclusive product experiences throughout the organization.
AMAZON • Seattle, WA • 2017—2020
Senior Technical Program Manager
Directed a 30-strong global engineering team at Amazon Global IT, delivering transformative UX research and quality assurance initiatives.
Achieved exceptional results through strategic leadership: 98% reduction in peak-event failures, successful migration of 27,000 employees with 99.998% accuracy, and implementation of AI-powered self-service solutions.
Spearheaded a company-wide hardware upgrade initiative that generated $8.6M in first-year productivity gains while optimizing system performance and user experience across all platforms.
microsoft • redmond, WA • 2008—2017
Program Manager II
Led Microsoft's Windows 10 upgrade testing program, partnering with industry leaders and PC manufacturers to ensure seamless transitions.
Engineered a groundbreaking universal tool for internal OS custom build and deployment achieving 99.999% reliability across 60 diverse system configurations, while reducing upgrade-related issues by 95%.
Managed comprehensive hardware standards and testing protocols for 120+ configurations, consistently delivering 100% on-time while earning multiple awards for excellence, including the prestigious Gold Star Award.
02
Education
BACHELOR Degree • universidad tecnologica del centro (UNITEC), venezuela
Information Engineering
At UNITEC, I deepened my understanding of user experience and information flows within organizations, learning to create effective systems through a blend of information theory, knowledge management, and practical project implementation. My coursework enhanced my ability to make data-driven decisions while designing intuitive solutions that optimize organizational performance.
associate degree • universidad tecnologica del centro (UNITEC), venezuela
Information Technology
At UNITEC, I developed expertise in complex problem-solving, computer programming, and innovative software design, gaining the technical foundation and creative mindset necessary to contribute meaningfully to technological advancement in the digital landscape.
03
Certificates
MIT xpRO
Designing and Building AI Products and Services
MIT CSAIL
Human Computer Interaction for User Experience Design Specialization
EXIN international
ITIL v2 Foundations in IT Management
microsoft corporation
Microsoft Certified Professional
04
Skills
Agile Program Management
Program Management
System Integration
Deployments / Migrations
Customer Experience
Product Management
Software Development
Quality Assurance
Project Management
Communications
Process Efficiency
Motivational Leadership
Data-Driven Innovator
Jira
Confluence
Figma
Snowflake
Adobe Creative Suite
Workfront
Windows • Linux • Mac
.NET Framework
C#
05
Languages
English
Spanish
06
Awards
Red Dot • 2024
Red Dot Design Award
Framer • 2023
Website of the Year
07
References
BEST BUY • SENIOR EXPERIENCE DESIGNER
Katie Calhoun
I had the pleasure of working closely with Oswaldo during our time at Best Buy. As a UX designer, I found Oswaldo to be an exceptional collaborator and a true advocate for user-centered design. His thoughtfulness, attention to detail, and commitment to putting users first steered our projects toward success. Moreover, Oswaldo’s collaborative spirit encouraged open dialogue and ensured that everyone felt valued.
I would love to partner with Oswaldo again, and I would recommend him as part of any product team!
Google Cloud • Technical Editor
Jay Hauser
Oswaldo asks the right questions at the right time to get the right results.
More importantly, he has long term vision. He sees what is, extrapolates what can be and then drives change to get there. I loved working with him because he was always direct. I never had to wonder where he was coming from. Would highly recommend him. He dives deep, takes ownership, and always puts the customer first.
STARBUCKS • SERVANT LEADER SOLUTIONS DELIVERY
Kelly Campbell Tiffany
I have rarely come across real talents who stand out like Oswaldo. I had the pleasure of partnering with Oswaldo in several different capacities at Microsoft, collaborating on various initiatives. Oswaldo has amazing thought leadership and a strong technical aptitude able to handle multiple complex projects. No matter how tense an issue or complex a project, Oswaldo made sure everyone left with a smile. As a team member or a leader, Oswaldo earns my highest recommendation.
Retired CTO • CIO • AI Director
Rafael Lara
Oswaldo's skills and experience make him a valuable asset to any technology team. I highly recommend him for any technical position.
These are some of the attributes I observed while he was in my team at Microsoft:
• Excellent problem solver with a strong analytical mindset
• Strong communication skills, both verbal and written
• Proven track record of successful project management and delivery
• Continuously seeks to learn and stay up-to-date with the latest technologies and trends
• Great personal interaction with Managers and Employees.
En DASH GROUP • Co-founder & CEO
Suzanne Leamer
I have had the pleasure of working with Oswaldo within Global IT Services at Amazon. I will always be grateful for his willingness to share his knowledge and the guidance he provided as I navigated the creation of my first narrative document (at Amazon, this is a valuable learning experience and critical skill to practice). Additionally, Oswaldo was a strong partner and ally in the delivery of two large-scale, complex programs. He's collaborative, fun, and I'd welcome the opportunity to work with him again.
NETAPP • SVP and GM, data services
Gagan Gulati
Oswaldo and I worked together on building efficient Windows 7 images for use inside Microsoft for a few months. Oswaldo has a great grasp on Windows setup internals including unattended installation. I found him to be understanding, flexible and easy to work with. He is passionate about this space and is willing to work hard to produce great results which showed when he built these images in record time and delivered on time.
MIcrosoft • Director, global partner solution incentives
Rene Garcia
As an internal customer of Oswaldo's services, I was greatly impressed with the quality and passion for excellence in his deliverables. He dealt with a great deal of complexity and greatly simplified the OS deployment process by focusing on the customer experience.
FORMER Tech program manager, emmy-winning writer, tv producer
Suzi Beerman
Oswaldo was tasked with managing the printer services for Microsoft employees worldwide. It was a job he performed incredibly well with limited resources and support. When the company was ready to move away from print and into digital, Oswaldo helped make the experience seamless, even for those who strongly resisted the concept. He was always professional, poised, and collaborative as he worked to dismantle a system he had helped build with an eye toward the greater good and the bottom line. He presented this new digital solution as a win-win and helped evangelize the opportunity across the company. I, and others, likely never felt so good about something so significant being taken away from us.
Oswaldo has always shown himself to be a dedicated employee, a creative thinker, a natural leader, and a compassionate human being. He would make an excellent addition to any team that needs calm focus and creative problem solving in a true team player.
SAP • senior program director
Juan Goni
Oswaldo is a passionate professional, extremely focused on customer satisfaction.
he has managed multiple projects in the company, touching thousands of users in multiple technologies. I enjoyed working with him.
08
Relevant Projects
BEST BUY • 2024
Streamline membership experience through UX improvements, Data consolidation, and API development
CHEWY - 2022
Replacement of legacy monolithic web platform with modern component-based one
Amazon - 2017
Development of a data-driven model to allocate appropriate computing equipment based on job family.
microsoft • 2016
Creation of an app and process to synchronize child bugs with the master bug's resolution and build information.
microsoft • 2012-2013
Microsoft Hardware Certification Requirements management process re-engineering
microsoft • 2007-2011
Design and implementation of Microsoft internal OS imaging and simplified deployment process
09
Ventures
Music Publishing • 2021
10
Contact
Socials