Denys L.
Director of Engineering, Global Payments & Tax Compliance @Upwork
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WORK HISTORY
Director of Engineering, Global Payments & Tax Compliance @Upwork
Portland, OR, US
Lead engineering teams responsible for Upwork\'s core payments infrastructure supporting global freelancer payments across 190+ countries with billions in annual transaction volumeStrategic Leadership & Innovation: Direct technical strategy for payments experience and tax compliance platform serving 15M+ users globally Built and scaled multinational engineering organization from 8 to 15+ engineers across Eastern Europe, North America, and CIS regions using remote-first leadership Delivered Transaction History improvements through cross-timezone collaboration with distributed teams Led cross-cultural communication in Ukrainian, English, and Russian across 8+ time zonesRegulatory Excellence & Compliance: Delivered critical W8-B flow improvements, reducing regulatory liability by 80% via global remote team execution Implemented DAC7 tax compliance and TIR reporting requirements across EU markets Launched VAT capabilities in 12+ new countries through remote coordination with international regulatory bodiesPlatform Modernization & Performance: Led Air3 migration and GraphQL implementation ahead of schedule, improving performance by 5-8% using DevOps with remote-first teams Spearheaded Braintree integration and Venmo launch (October 2024) via distributed engineering pods Implemented Autodisbursement Communication updates enhancing user engagement by 25%
EDUCATION
Kherson Regional Lyceum
High School Diploma, Physics, Mathematics, Chemistry, Biology
National Technical University of Ukraine 'Kyiv Polytechnic Institute'
Bachelor of Engineering (B.E.), Computer Science - Applied System Analysis
ABOUT DENYS L.
Engineering leader with 20+ years building scalable web applications and leading high-performing teams in fintech and payments. Currently directing engineering for Upwork\'s Payments Experience & Tax Platform, serving millions of users globally across 190+ countries.KEY ACHIEVEMENTS: Led engineering teams through 4+ years of payments platform evolution at Upwork Architected front-end systems supporting billions in transaction volume Built and scaled engineering teams from individual contributor to director level (3→15+ engineers) Expert in translating complex business requirements into technical solutions Delivered critical EU regulatory compliance (DAC7, GDPR, VAT) ensuring market access Proven track record in AI/ML integration, payment optimization, and cross-border fintech solutions Spearheaded digital transformation initiatives across enterprise-scale, high-growth environments using Agile and DevOps methodologiesGLOBAL LEADERSHIP:Fluent in Ukrainian, English, and Russian - enabling effective communication with diverse international teams, stakeholders, and regulatory bodies across Eastern Europe, North America, and CIS markets.REMOTE-FIRST LEADERSHIP:Portland-based with 8+ years managing distributed, global engineering teams across multiple time zones. Expert in building high-performing remote cultures and delivering complex technical projects with international stakeholders.PERSONAL INTERESTS:Passionate about home automation (Home Assistant ecosystem), self-hosting infrastructure (Docker, Debian, UniFi, Synology), hardware prototyping, and photography. Weekend woodworking enthusiast and avid gamer across multiple platforms.Open to strategic leadership opportunities in fintech, payments, and regulatory technology.
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