We are looking for a Director of Software Development who will own the equity and enrollment technology stack end to end, from the core enrollment services our employees rely on through the equity systems behind them.
You will lead the engineering organization responsible for building industry-leading products and experiences for Amazonians as they interact with their benefits — stock, retirement, and enrollment.
You will set the technical vision, drive architectural decisions, and deliver working software on a 4–6 week cadence.
You will work at the intersection of Artificial Intelligence (AI)/Machine Learning (ML), enterprise platform engineering, regulatory compliance, and employee experience — at a scale no other employer or vendor has reached.
Two outcomes define success in this role: (1) World-class customer experience — build conversational, intuitive technology that makes complex benefits interactions simple and human.
(2) Cost efficiency through AI — embed AI across the software development life cycle (SDLC) to reduce cost, accelerate delivery, and increase system reliability.
This is a role for a builder who thinks in systems, not features.
You will hold a 10-year architectural vision and ship production software every 4–6 weeks.
What you will do: - Own the full technical strategy and roadmap for equity and enrollment systems serving millions of Amazonians.
- Lead and grow a multi-team, multi-disciplinary engineering organization, maintaining both technical depth and customer proximity.
- Drive adoption of AI/ML to improve developer productivity, system quality, and the employee experience.
- Partner with product, compliance, and benefits operations to build systems that meet regulatory requirements without sacrificing speed or experience.
- Set and hold a high technical bar: scalable architecture, operational excellence, and a strong engineering culture.
- Define and deliver measurable outcomes — including [key cost, reliability, and customer experience metrics your org tracks] — and communicate progress to senior leadership.
What you bring: - Demonstrated history building and leading large engineering organizations that delivered large-scale, customer-facing products on scalable architecture.
- Deep understanding of customer experience, system architecture, and technical implementation details on products you have personally led.
- Proven ability to mobilize multi-team, multi-disciplinary organizations while staying close to customers and the details.
- Experience applying AI/ML to engineering systems, developer tooling, or customer-facing products.
- Track record of translating a long-term architectural vision into incremental, shippable milestones. Key job responsibilities
- AI-Native Platform Strategy: Own the technical vision for Equity and Enrollment technology, from human-processed workflows to AI-native orchestration — autonomous agents, agentic workflows, and humans for ambiguous gaps.
- Conversational Experience: Drive conversational and voice-based leave management replacing callback queues with instant, contextual resolution.
- Partner with Industry leaders: Leverage their expertise combined with your own experience to create and execute on an innovative technical product strategy.
- Customer Experience: Deep understanding on how to improve the customer experience using data and anecdotes.
You will look around corners to proactively mitigate obstacles and get ahead of industry trends.
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.