01
Experience
The Herewhat Company • SEATTLE, WA • 2024—present
Product Manager - AI
At Herewhat, I lead innovation initiatives at the crossroads of AI and enterprise workflow design.
Designed and deployed an AI-driven email classification system for Outlook.com, handling hundreds of messages daily, boosting accuracy by 40% and reducing manual tagging effort by 75%.
Simplified creative and business workflows by automating repetitive tasks, leading to a 30% reduction in processing time across departments.
Oversaw roadmap strategy, architecture decisions, and cross-functional delivery.
BEST BUY • SEATTLE, WA • 2023—2024
Senior Product Manager and Senior Technical Program Manager (Split position)
Led the modernization of Best Buy’s membership & retention platform, unifying fragmented systems into a seamless, customer-focused experience.
Consolidated 5+ disconnected data sources into a single source of truth for 1.2M+ global users.
Increased member retention by 30%, improved refund accuracy to 99.8%, and boosted program quality metrics by 60%.
Managed a team of 15 cross-functional stakeholders, including engineering, marketing, and operations.
Delivered both strategic roadmap planning and hands-on technical execution, improving speed to market and customer satisfaction.
CHEWY • BELLEVUE, WA • 2022
Staff Technical Product Manager
Drove a platform-wide transformation to support Chewy’s growth and customer experience initiatives.
Rebuilt a legacy monolithic web platform into a modern, component-based architecture (React/Node/Cloud).
Achieved a 50% reduction in page load latency and tripled deployment frequency, improving agility and scalability.
Led release coordination across multiple engineering teams and departments, streamlining collaboration and delivery.
AMAZON • Seattle, WA • 2017—2022
Senior Technical Program Manager
Managed global initiatives improving employee systems and operational scalability for Amazon’s rapid workforce growth.
Directed a 27,000-employee migration to new authentication systems with a 99.998% success rate, minimizing disruption and risk.
Delivered a $8.6M annual productivity boost through data-driven hardware upgrade strategies.
Owned monthly releases of a customer-facing application supporting 1.2M+ global users, ensuring on-time delivery and continuous quality improvements.
Coordinated cross-regional teams in NA, EMEA, and APAC, aligning technical strategy with business operations.
Program Manager II
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
Product & Program Management
Agile (Kanban, Scrum)
Waterfall
Product Lifecycle Ownership
Strategic Roadmapping
OKRs
Stakeholder Management
Technical Leadership
Systems Architecture
Cloud Migrations
Deployments
Automation
Data-Driven Decision Making
Tools & Platforms
Jira
Azure DevOps
Confluence
AWS
Azure
Google Cloud Platform (GCP)
Figma
Framer
User Experience
User Research
Design Thinking
Process Simplification
Customer Advocacy
User-Centric Design
languages
English (Fluent)
Spanish (Native)
05
Awards
microsoft • 2012
Ship It! • Windows 10
microsoft • 2010
Ship It! • Microsoft Forefront Endpoint Protection 2010
microsoft • 2009
Gold Star • Outstanding performance and commitment to the program management process.
microsoft • 2009
Ship It! • Windows 7
microsoft • 2009
Ship It! • Microsoft Spec Explorer 3.0
microsoft • 2008
Ship It! • Windows Vista Service Pack 1
microsoft • 2006
Ship It! • Exchange Server 2007
microsoft • 2001
Ship It! • Windows XP
06
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.
07
Relevant Projects
The Herewhat Company • 2025
AI-Powered Email Classification System
Designed and implemented a hybrid rule-based and machine learning classifier for Microsoft Outlook.com to intelligently categorize incoming messages. Improved classification accuracy by 40%, reduced manual tagging effort by 75%, and ensured critical tags like Outlook.com were preserved without disruption. Scaled the system to process hundreds of messages daily, providing reliable automation for personal productivity and experimentation.
Tools / Infrastructure: Python, Machine Learning, Microsoft Graph API, ngrok, Cloudflare Tunnels, Webhooks, OAuth, LLM (ChatGPT 40-mini).
Scope / Team: Owned Spec, development, monitoring, dashboard design, overseeing roadmap strategy, architecture decisions, and end-to-end deployment.
BEST BUY • 2024
Membership Platform Simplification & API Unification
Consolidated five legacy data sources into a unified member profile API, enabling consistent data across mobile, web, and in-store platforms. Redesigned customer-facing flows to reduce friction in membership onboarding and retention. Outcomes included a 30% increase in member retention, 40% faster data lookup times, and a 20% reduction in customer support tickets related to mismatched member data.
Tools / Infrastructure: Jira, Confluence, REST APIs, GraphQL, GCP Cloud SQL, semantic engine for data interpretation and relationship mapping.
Scope / Team: Led a cross-functional team of nine members — five developers, one development manager, one UX designer, one product manager, and myself as the technical program manager — while collaborating closely with marketing, operations, and support teams.
CHEWY - 2022
Web Platform Modernization (Monolith → Component Architecture)
Migrated a legacy monolithic platform to a component-based architecture (React + Node.js + microservices) to improve maintainability and speed of feature delivery. Reduced page load latency by ~50%, improved deployment frequency by 3× (from monthly to biweekly), and cut down maintenance overhead by ~40%. Enhanced user satisfaction scores by ~20% post-launch.
Tools / Infrastructure: React, Node.js, Containerization, CI/CD pipelines.
Team & Ownership: Led roadmap, architecture decisions, and delivery across teams; managed 5 engineers.
Amazon - 2020
Authentication Migration
Led the migration of 27,000 employees to a new enterprise authentication platform, modernizing access control systems and improving security posture across Amazon’s global workforce. Developed and executed a comprehensive migration strategy that ensured a 99.998% success rate with minimal downtime or disruption to business operations. This initiative streamlined user access management, reduced operational overhead, and provided a scalable foundation for future identity and security initiatives.
Tools / Infrastructure: Active Directory, LDAP, AWS Identity and Access Management (IAM), Amazon SIM, internal automation and monitoring tools.
Scope / Team: Coordinated migration efforts across three global regions (NA, EMEA, APAC), partnering with regional engineering, security, and support teams to align processes and execute a seamless transition.
Amazon - 2017
Equipment Allocation Model for Job Families
Developed a data-driven allocation model to determine the optimal computing equipment for each job family based on real-world usage patterns and productivity metrics. Leveraged Lakeside Software SysTrack to analyze performance data from existing hardware, quantify productivity losses, and validate the benefits of proposed new standards. This initiative eliminated over-provisioning and under-performance, resulting in $8.6M in productivity gains during the first year of implementation. The model continuously informed hardware lifecycle planning, ensuring employees had the right tools for their roles while optimizing costs at scale.
Tools / Infrastructure: Lakeside Software SysTrack, internal procurement and asset management systems.
Scope / Team: Rolled out globally across 30+ job families and thousands of employees; partnered closely with procurement, finance, and IT leadership teams to design strategy and oversee implementation.
microsoft • 2016
Bug Sync App & Process Improvement
Architected and delivered an internal tool to automatically synchronize child bug tickets with master bug resolutions and build metadata. Reduced tracking errors by ~80%, improved transparency for engineering leads on status, and sped up resolution cycles for large bug clusters by ~50%. Rolled out to all teams involved in Windows build/QA pipelines.
Tech / tools: Visual Studio Team Services (VSTS), C#, VSTS access libraries.
Team / Ownership: Owned spec, development, test, release and operation. Reduced bug tracking from 20 minutes to less than 1 minute per bug for the entire Windows Partner Ecosystem organization.
microsoft • 2012-2013
Hardware Certification Process Re-Engineering
Worked as part of the Windows Hardware Certification team, which coordinated with all global OEMs and peripheral manufacturers certifying their products for Windows — covering everything from complete systems to individual components and devices. This effort ensured that every Windows-compatible product worldwide met rigorous and evolving hardware standards.
Independently designed and implemented an automated system to consolidate over 3,500 individual hardware requirements sourced from 27+ Windows feature teams. The system generated pre-validated XML files for testing within the Windows Hardware Certification Kit (HCK) and automatically produced the final public documentation published to microsoft.com.
This innovation eliminated human error, reduced document generation time from weeks to minutes, and provided each feature team with validated requirements for consistent and efficient testing — fundamentally transforming how hardware requirements were managed and distributed globally.
Tools / Infrastructure: Custom-built requirements management and document generation system, XML data pipelines, Windows Hardware Certification Kit (HCK), internal collaboration platforms.
Scope / Team: Integrated with 27+ internal feature teams and all global OEMs and peripheral vendors through the broader hardware certification organization.
microsoft • 2007-2011
Enterprise OS Imaging & Deployment Simplification
Designed a universal internal OS imaging framework, consolidating 120+ system types into a few streamlined image configurations. Reduced deployment cycle from days to hours, achieved >99.9% reliability, and cut configuration drift and support incidents by ~80%. Managed regional deployment trains, hardware compatibility testing, and hardware vendor certification partnership.
Tools / Infrastructure: Windows Assessment and Deployment Kit (Windows ADK), DISM, WinPE, WinRE, Windows Deployment Services (WDS), C#, XAML, XML, Test lab with 120 system configurations.
Scope / Team: ~16K systems imaged/month, 150,000 systems worldwide, managed a team of 1 test manager, 2 testers, 4 PC manufacturers (OEM) and cross-collaboration with Windows, Office, and OEM divisions.
08
Contact
I’m currently based in Seattle, WA and open to opportunities where I can drive enterprise-scale transformation and measurable impact.
Reach me directly at:
or connect with me on LinkedIn.