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Ryan Darling
Los Angeles,CA
Work Preference
Summary
Strategic Product Leader with 15+ years of experience driving high-growth e-commerce and platform trajectories from $200M to over $1B in annual revenue. Expert in navigating complex organizational silos, driving cross-functional diplomacy, and managing high-stakes financial and geopolitical crisis responses. Direct partner to the CTO and Executive Suite, known for applying deep data and financial fluency to bridge technical architecture and business-critical outcomes. Unique ability to protect teams from legacy systemic drag while rallying organizations toward measurable delivery under pressure. Proven experience delivering complex software projects and managing customer needs.
Overview
12
12
years of professional experience
Work History
Principal Product Manager
Fabletics (TechStyle Fashion Group)
El Segundo, CA
05.2022 - 02.2026
- Platform Scale & Multi-Vertical Expansion: Spearheaded technology operations, product roadmaps, and cross-functional coordination for four major category launches (Men's, Shapewear, Scrubs, Denim), taking the platform from 1 to 5 verticals and enabling 5x revenue growth ($1B+ ARR).
- Non-Cash Token Membership System: Led re-architecture of monthly membership from cash-credit to non-cash token system; navigated escheatment law and revenue recognition compliance. Transformed customer utility from breakable $50 cash credit to single-use non-breakable token valued up to $100, with expiration and breakage capitalization - improving VIP LTV and balance sheet liability management.
- Billing Architecture Overhauls: Spearheaded major billing architecture rewrites for legal, compliance, and accounting needs; navigated cross-functional diplomacy between Engineering, Finance, and Legal under high-stakes constraints.
- Enterprise Tariff Response (8-Month Sprint): Led 8-month multivariate testing campaign across pricing UI, surcharge logic, and disclosure language to neutralize tariff margin erosion; defended VIP gross margins with zero significant member churn.
- Service Reliability & Observability: Eliminated recurring high-traffic outages by designing a custom service-monitoring dashboard and proactive alerting framework; transitioned the team from reactive firefighting to 99.9% uptime reliability during peak product launches.
- Writing User Stories and Acceptance Criteria for Product Features
Director of Product
Fabletics (TechStyle Fashion Group)
El Segundo, CA
08.2020 - 05.2022
- Department Operating Architecture: Led strategic positioning of product and technology organization-wide; established operating pillars, structural roadmaps, and governance frameworks that connected executive strategy with engineering execution.
- COVID-19 Pivot: Stabilized VIP growth and subscription flows by aligning retail fleet technology with digital e-commerce roadmaps under volatile market conditions.
- PM Organization Scaling: Scaled the PM organization; established 'Source of Truth' frameworks in Jira and Confluence to improve executive visibility and speed-to-market.
- KPI Stewardship: Collaborated with Finance and Marketing to align technical investments with core business levers including AOV, UPT, and member retention.
- Managed change requests and development phases to align with project goals.
Senior Product Manager, Digital Experience
Fabletics (TechStyle Fashion Group)
El Segundo, CA
04.2019 - 08.2020
- Waitlist Architecture + Auto-Purchase Engine: Developed and scaled the company's first full waitlist system, including back-in-stock notifications and auto-purchase triggers; dramatically improved inventory predictability, enabled granular customer interest segmentation, and built structural launch-hype mechanics for new product drops.
- Mystery Box Innovation: Conceptualized and launched a personalized Mystery Box line; architected a custom GraphQL backend to manage complex bundling logic and inventory concealment.
- Prospect to VIP Journey: Owned the end-to-end conversion journey from prospect registration to VIP subscription; drove improvements through optimized registration flows, PDP enhancements, and rigorous A/B testing across checkout UX.
- Business Vertical Expansion: Led buildout of two brand new business verticals and a major rework of subscription architecture.
- Prioritized Customer Needs and Build Strong Relationships
Product Lead & Staff Product Manager
Tech Holding & Ninety Plus Wine
Los Angeles, CA
01.2018 - 03.2019
- ML-Powered E-Commerce Platform: Managed design and launch of a React.js platform with proprietary machine-learning recommendation engine based on user taste profiles; drove personalization at scale.
- Strategic Business Development: Spearheaded proposal development for major entertainment industry clients, achieving a 100% win rate on competitive bids.
- Team Leadership: Directed hiring, onboarding, and mentoring of the firm's Design and UX staff to support a growing portfolio of client engagements.
Product Manager
AutoVitals Inc.
Santa Barbara, CA
06.2016 - 01.2018
- Enterprise Churn Reduction: Reduced churn from 2.5% to 1.7%, saving approximately $130K in ACV through data-driven reporting repairs and systemic integrity fixes.
- Client KPI Visualization: Designed the first client-facing KPI Trend Graphs, creating a shared data language between account teams and clients to drive retention.
Product Specialist
AutoVitals Inc.
Santa Barbara, CA
02.2014 - 06.2016
- API-Based Data Sourcing Tool: Developed an API-based data sourcing tool to replace manual user emulation; stabilized KPI reporting and reduced significant resource drain.
Education
Communications
University of California, Santa Barbara
01-2013
Skills
- Organizational Diplomacy: Stakeholder influence, product evangelism, executive communications, cross-functional alignment
- Financial & Data Fluency: Unit economics, margin optimization, revenue recognition modeling, tariff response, A/B pricing
- Strategic Systems: Multi-vertical scaling, opportunity solution trees, RICE/WSJF, operational architecture
- Technical Execution: GraphQL API management, microservices, headless CMS, WMS/PLM/ERP integrations, service observability
- AI & Analytics: LLM integration, assortment testing platforms, attribution engines, LaunchDarkly live backend data
- Innovation & Change Management: AI-first product discovery workflows, DX platform design, organizational adoption
- Product roadmap development
- Data-driven decision making
- Pricing strategy optimization
- Subscription model design
- Subscription economics
Affiliations
- Advisor, University of San Francisco AI Marketing Executive Leadership Program
Timeline
Principal Product Manager
Fabletics (TechStyle Fashion Group)
05.2022 - 02.2026
Director of Product
Fabletics (TechStyle Fashion Group)
08.2020 - 05.2022
Senior Product Manager, Digital Experience
Fabletics (TechStyle Fashion Group)
04.2019 - 08.2020
Product Lead & Staff Product Manager
Tech Holding & Ninety Plus Wine
01.2018 - 03.2019
Product Manager
AutoVitals Inc.
06.2016 - 01.2018
Product Specialist
AutoVitals Inc.
02.2014 - 06.2016
Communications
University of California, Santa Barbara