A to Z Leave & Accom Tech, Amazonian Experience and Technology
About the role
We are looking for a Director of Software Development to lead the technology organization behind Amazon's leave and accommodations platform — the largest, most automated employer-operated absence management system in the world.
Responsibilities
AI-Native Platform Strategy: Own the technical vision for transforming leave and accommodations from human-processed workflows to AI-native orchestration — autonomous agents for straightforward cases, agentic workflows for ambiguous cases, human specialists for the rest.
Autonomous Resolution: Lead development of an orchestration engine that transforms hundreds of leave policies into machine-executable workflows achieving majority auto-adjudication and zero-touch completion.
Compliance & Governance: Own the structural separation of execution and governance — every case gets automated compliance audit regardless of whether a human or AI decided it.
Composable Architecture: Drive API-first, tool-native design so all capabilities are callable, composable, and ready for broader platform integration and eventual external productization.
Clinical Intelligence: Own AI systems connecting medical information to workplace decisions — job-matching, restriction extraction, dynamic documentation, and duration management.
Conversational Experience: Drive conversational and voice-based leave management replacing callback queues with instant, contextual resolution.
Scale & Modernization: Ensure durability at massive scale while completing migration from batch-processing legacy systems to event-driven architecture.
Team Transformation: Lead a technology organization through the shift from volume-driven to complexity-driven staffing, building programs that upskill domain experts into AI Specialists.
Qualifications
Bachelor's degree in Computer Science, Engineering, or related technical field (or equivalent experience)
10+ years of software development experience with increasing scope and complexity
10+ years in senior engineering leadership roles managing multiple teams and senior managers
Experience building and operating large-scale distributed systems processing millions of transactions daily
Experience leading AI/ML-powered product development from concept through production at scale
Experience with platform migrations, legacy system deprecation, and enterprise system modernization
Track record of delivering measurable business outcomes (cost reduction, efficiency gains, quality improvement) through technology
Preferred Qualifications
Experience in HR technology, benefits administration, insurance/claims processing, or regulated workflow automation
Deep expertise in agentic AI architectures, LLM-based systems, and autonomous workflow orchestration
Experience building compliance-critical systems in regulated environments (healthcare, financial services, employment law)
Experience with event-driven architectures, API-first design, and composable service ecosystems
Demonstrated ability to lead through ambiguity at the intersection of technology, policy, and operations
Experience managing technology organizations through operating model transformations (manual → automated → AI-native)
Strong written communication skills; experience with narrative-driven product development (PR/FAQ or equivalent)
Experience partnering with legal, compliance, and policy teams on technology decisions with regulatory implications
Track record of building and scaling engineering teams across multiple geographies
Experience with clinical or medical data systems, NLP/document intelligence, or decision-support systems