A to Z Leave & Accom Tech, Amazonian Experience and Technology

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. This platform processes millions of leave and accommodation requests annually across 60+ countries, administers nearly $1B in annual benefit payments at greater than 99.99% accuracy, and serves over 1.5 million employees through their most consequential workplace moments.
You will own the end-to-end technology strategy and delivery for two interconnected platforms that together manage the full spectrum of employee time-away and workplace modification. The core challenge: transforming a system built around human case managers into one where AI agents resolve straightforward cases autonomously, handle ambiguous cases with human oversight, and free human specialists to concentrate on the cases that genuinely require judgment and empathy. You will build autonomous adjudication engines, compliance governance agents, clinical job-matching systems, conversational AI experiences, and the composable service architecture that positions this platform as the foundation for a unified employee health experience — and eventually an external product.
This is a role for a builder who thinks in systems, not features. Someone who can hold a 10-year architectural vision while shipping working software every 4–6 weeks. You will work at the intersection of AI/ML, enterprise platform engineering, regulatory compliance, and employee experience — at a scale and complexity no other employer or vendor has achieved. If you want to build something that has never existed before and that directly impacts millions of people during their most vulnerable moments, this is the job.

Key job 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.

A day in the life
You might review a PR/FAQ for autonomous adjudication, dive deep on return-to-work defect rates, partner with Legal on compliance implications of a new AI workflow, or work with AI Specialists building micro-automations. Your stakeholders span HR leadership, Operations, Legal, data science, and platform teams across Amazon's employee experience ecosystem. Your customers are over 1.5 million employees navigating health crises, new parenthood, and workplace modifications — plus the tens of thousands of HR professionals and managers supporting them. Problems range from badge lockouts on day one back to building the world's first closed-loop accommodation verification system.

About the team
A to Z Leave and Accommodations answers the question every employee eventually asks: What happens when I can't work — and what happens when I'm ready to come back? We operate the world's largest employer-operated absence management platform, serving over 1.5 million employees across 60+ countries. Our mission: make every interaction instant when the rules are clear, empathetic when the situation is complex, and verified as delivered — not just approved. We're AI-native builders who ship in 4–6 week cycles and measure by capabilities reaching customers. We're building toward a unified health experience no vendor can match.

Basic 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)
Track record of building platforms designed for external productization or multi-tenant operation
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

Amazon is an equal opportunity employer and does not discriminate on the basis of protected veteran status, disability, or other legally protected status.

Our inclusive culture empowers Amazonians to deliver the best results for our customers. If you have a disability and need a workplace accommodation or adjustment during the application and hiring process, including support for the interview or onboarding process, please visit https://amazon.jobs/content/en/how-we-hire/accommodations for more information. If the country/region you’re applying in isn’t listed, please contact your Recruiting Partner.

The base salary range for this position is listed below. Your Amazon package will include sign-on payments and restricted stock units (RSUs). Final compensation will be determined based on factors including experience, qualifications, and location. Amazon also offers comprehensive benefits including health insurance (medical, dental, vision, prescription, Basic Life & AD&D insurance and option for Supplemental life plans, EAP, Mental Health Support, Medical Advice Line, Flexible Spending Accounts, Adoption and Surrogacy Reimbursement coverage), 401(k) matching, paid time off, and parental leave. Learn more about our benefits at https://amazon.jobs/en/benefits.

USA, WA, Bellevue - 264,100.00 - 350,000.00 USD annually