We're looking for a Director of Software Development to own Amazon's equity and enrollment technology stack end to end, building the systems that millions of Amazonians and their family members rely on to enroll in their benefits and to receive, hold, and transact the equity they earn. Equity and enrollment run as an independent technology domain that brings product, software development, and benefits administration under one roof. You'll own benefits enrollment, the member-facing experience (the A to Z app and AZA, our AI assistant), and the equity and retirement systems behind it, including managing all Amazon RSU grants through to the sale on the vest date and handover to stock brokers, alongside U.S. 401(k) and international retirement savings. No other employer or vendor has built benefits and equity technology at this scale and complexity. You'll set the technical vision, drive the architecture, and ship production software on a 4-6 week cadence while leading a world-class, multi-disciplinary organization of engineers, product leaders, and benefits administrators. This is a Native AI organization. We're moving from AI that assists builders to AI that owns the mechanical middle of building and running software, while our people own the judgment and accountability. Our north star is a recursively self-improving loop. You give the system a goal, and it builds, ships, and keeps evolving the result, with humans at the gates that decide what is correct and what ships. Two outcomes define success. The first is a world-class customer experience, intuitive technology that makes complex enrollment and equity decisions simple and human. The second is cost efficiency through AI, embedded across how we build and operate software to cut cost, accelerate delivery, and improve reliability. This is a role for a builder who thinks in systems, not features, someone who holds a 10-year architectural vision and still ships every few weeks. If you want to build something that has never existed before, at a scale no one else can match, this is the role. Key job responsibilities • Own the equity and enrollment stack. Set the vision and roadmap for benefits enrollment, the member-facing experience, and the equity and retirement systems, including all Amazon RSU grants through to sale on the vest date and handover to stock brokers, U.S. 401(k), and international retirement savings, serving millions of Amazonians and their families. • Lead a world-class, multi-disciplinary organization. Direct an org spanning product, software development, and benefits administration, keeping technical depth and customer proximity as it scales. • Build the Native AI operating model. Move the organization from human-driven workflows toward one where AI agents own routine implementation and people own judgment, climbing the levels of autonomy from closed build loops to self-evolving products. • Deliver an agentic enrollment experience. Replace static enrollment pages and forms with instant, contextual resolution, so members ask questions and make elections in a single experience. • Partner across the mandate. Work with healthcare and benefit policy and program owners, equity and financial professionals, compliance, and legal partners to build customer obsesses products that meet regulatory and business requirements. • Hold a high engineering bar. Scalable architecture, operational excellence, and a strong engineering culture. About the team No employer or vendor has built what we are building — a benefits technology platform at the scale and complexity of Amazon. This team directly impacts millions of people at moments that matter: when they enroll in healthcare, vest equity, or plan for retirement. If you want to build something that has never existed before, this is the role. Basic qualifications - Bachelor’s degree in Computer Science or related field of study - 10+ years leading software development teams - Experience delivering technology products - Demonstrated ability to work across disciplines with product, engineering, research, and design - Strong analytical and quantitative skills; ability to use hard data/metrics to drive actions - Attention to detail including proven ability to manage multiple, competing priorities simultaneously - Excellent written and verbal communication skills 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, Seattle - 264,100.00 - 350,000.00 USD annually