Michael Winters

Provided fractional product leadership for local not-for-profit, retail, and e-commerce businesses on product development strategy and AI tool integration as an independent consultant.

Built Chewy's first automated compliance analytics platform from the ground up, re-architecting instrumentation across all product surfaces into a unified metrics framework. Eliminated 50+ manually corrected metrics, saved 20 hours/week in analyst capacity, and shifted the organization from reactive execution to outcome-driven prioritization.

Hand-selected by CTO and CISO to stabilize GRC and Privacy Technology teams during a critical leadership transition; led PCI DSS 4.0 readiness across three business entities through Attestation of Compliance delivery, reducing audit cycle time by 50%.

Operationalized Chewy's CCPA/DSAR compliance program at enterprise scale, processing 2,000–3,000+ data subject requests bi-weekly with a 4-day average completion time (91% faster than the 45-day SLA). Deployed PII automation to production, launched BigID data classification across 29+ data sources, and managed a 56-application User Access Review program via SailPoint integration.

Directed product strategy and execution of "Chewy Heartbeat," a product-led growth initiative and analytics dashboard delivering the company's first unified view of customer behavior and conversion performance across the full purchase funnel, establishing a new standard for executive-level data visibility.

Designed and deployed Chewy's first AI/LLM enablement program for Product Managers, equipping 20+ product teams with practical fluency across roadmapping, PRD drafting, and data analysis workflows. Drove measurable cost avoidance through reduced manual effort and faster decision cycles.

Implemented a quantitative prioritization framework that reduced peak-season escalations to zero across 20+ product teams, improving roadmap transparency for executive stakeholders through data-driven prioritization.

Directly managed 13 reports across global teams; mentored 20% to promotion and turned around 30% of underperformers within 12 months through structured coaching and performance management.

Led a 21-person cross-functional team (data scientists, hardware engineers, software engineers) as technical and strategic owner of Amazon's computer vision defect detection platform. Deployed across 300+ fulfillment centers, drove an 11% reduction in item defect rates, and owned the full technical roadmap from ML research through frontline operational rollout.

Directed end-to-end technical planning and execution of Project Kariba, a zero-to-one upstream fulfillment model routing bulk inventory to low-cost staging nodes. Avoided an estimated $293M in supply chain costs over three years through a ground-up cost model, product selection strategy, and 3PL operating framework. Solution remains in active production and continues to scale.

Led ground-up re-architecture of Amazon's largest operational metrics platform (30,000 daily users). Reduced page load times from 3 minutes to 5 seconds (97% improvement), replaced manual Excel reporting across 300 fulfillment centers, cut report creation time by 80%, and drove 2× year-over-year user engagement growth.

Identified a critical gap in operational reporting across the Amazon fulfillment center network and led development of a custom dashboard generator to close it, enabling on-demand metric tracking from floor operations through VP level. Drove adoption through a three-month early access pilot and nationwide roadshow; 100+ custom dashboards created in the first month, cutting business review prep by approximately 10 hours per site and eliminating an estimated 3,000 hours of weekly operational overhead across the 300-site network.

Drove $32M in cost avoidance through platform optimization and technical debt reduction while maintaining 100% system uptime throughout major architectural migrations.

Managed a team of 3 managers and 30+ individual contributors; drove 4 high-impact promotions and maintained a high talent bar through performance-based people leadership.

Directed a 5-day mission-critical turnaround of pandemic-response tooling, ensuring uninterrupted global delivery of essential goods during unprecedented supply chain disruption.

Designed and launched day-one customer support capability for Apple Watch 1.0, building custom real-time support solutions for a product category with no screen-sharing capability. Achieved 96% Customer Satisfaction (CSAT) across all Apple contact centers worldwide at launch.

Delivered real-time video, screen sharing, and chatbot integrations into Apple's core contact center platform across five global locations, equipping 2,000+ support agents with expanded capabilities.

Led technical partner relationship between Google and Walmart as primary liaison, managing implementation of 10,000+ daily product listing ads generating $10M+ in monthly revenue.