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Stephen Rossman

@stephenrossman

Senior software engineer building healthcare, observability, and AI-powered platforms at scale.

United States
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What I'm looking for

I’m looking for a team where I can build cloud-native, high-scale systems—mixing product delivery with reliability, performance, and AI-enabled workflows—and partner closely with product while mentoring engineers.

I’m a Senior Software Engineer with 12 years of experience building healthcare, observability, and global marketplace platforms at Amazon, Datadog, and Airbnb. I lead end-to-end delivery across cloud-native microservices, AI-powered workflows, and high-scale distributed systems.

At Amazon (Amazon One Medical), I expanded telehealth capabilities by launching Amazon Clinic and building HIPAA-compliant microservices for intake, provider matching, visits, and prescriptions integrated with EHR using FHIR. I owned backend orchestration with event-driven asynchronous processing to stabilize high-volume workflows, improve reliability under peak load, and cut failed requests.

I also strengthened performance and AI productivity by optimizing APIs (reducing latency 30%) and building AI-powered patient summarization and triage support (reducing manual review effort 30%). Earlier at Datadog and Airbnb, I delivered reliability and modernization—defining SLIs/SLOs and incident response at Datadog, and improving booking experiences and conversion through server-side rendering and migration from legacy systems at Airbnb.

Experience

Work history, roles, and key accomplishments

Amazon logoAM
Current

Senior Software Engineer

Jul 2021 - Present (4 years 11 months)

Led expansion of Amazon One Medical telehealth and clinical workflows, building HIPAA-compliant microservices (intake, provider matching, visits, prescriptions) integrated with EHR via FHIR, supporting millions of patients. Improved reliability and performance by making intake/visit orchestration event-driven, reducing failed requests under peak load, cutting latency 30% via caching/query tuning,

Datadog logoDA

Site Reliability Engineer

Dec 2016 - Jun 2021 (4 years 6 months)

Owned reliability of telemetry ingestion and alerting pipelines across thousands of services, designing Kafka-based ingestion, normalization, and ETL flows to handle backpressure, retries, and uneven traffic. Defined SLIs/SLOs and drove incident response, reducing repeat production issues by 40% and scaling ingestion/storage infrastructure on Kubernetes and GCP/AWS.

Airbnb logoAI

Software Engineer

Jun 2013 - Dec 2016 (3 years 6 months)

Contributed to global booking and listing platforms, implementing server-side rendered React flows that reduced initial load time by 25% and improved booking conversion by 5% through faster search-to-checkout experiences. Built and hardened microservices for reservation and payment, adding retries and idempotent endpoints that reduced peak booking errors by 20% and refactoring legacy components to

Education

Degrees, certifications, and relevant coursework

University of Wisconsin–Madison logoUW

University of Wisconsin–Madison

Bachelor of Science, Computer Science

2009 - 2013

Earned a Bachelor of Science in Computer Science at the University of Wisconsin–Madison from 2009 to 2013.

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