cover_letter / art_pEv6OYN1I6w

Dear Oscar Hiring Team, Oscar set out to build health insurance that behaves like a doctor in the family — a mission that demands not just empathy, but rigorous platform engineering and operational discipline at scale. That combination is exactly where I have spent the last twelve years: building developer-facing platforms, scaling infrastructure to hundreds of millions of engagements, and shipping tooling that makes complex systems legible to the people who depend on them. The Group Product Manager, Member Coverage & Support Platform role sits at the intersection of those capabilities, and it is the kind of problem I want to work on. ## Technical and Platform Foundation At Intuit, I owned the developer platform infrastructure that underpinned QuickBooks, TurboTax, Mint, Mailchimp, and Credit Karma. The ICE platform I led scaled from 6,000 to 50,000 transactions per second via an rSocket migration supporting approximately 1.5 million concurrent connections at sub-25ms TP99 — a throughput and reliability challenge directly analogous to the seasonal peaks and high-pressure moments Oscar's coverage and billing platforms face during open enrollment. I also delivered the ICE Self-Service platform (DevPortal, GitOps configuration, ICE Playground), compressing developer onboarding from two to three weeks down to minutes in pre-production and under 24 hours for production, while mitigating over $1M in projected operating cost growth. That work required translating deeply technical platform constraints into clear priorities for non-technical business stakeholders — a skill the Oscar role calls out explicitly. At Splunk, I owned a portfolio of Go microservices (Search Service, Search Catalog) and a PostgreSQL-backed metadata service, building roadmaps, PRDs, and acceptance criteria for Splunk Cloud Services. I led a query performance initiative for a beta enterprise customer that achieved up to 10x search performance improvements — work that required understanding the full stack, coordinating across engineering and operations, and making tradeoff decisions under real customer pressure. On the AI side, I have built production multi-agent orchestration (OpenClaw framework with gateway protocol and subagent delegation), RAG retrieval pipelines with multi-provider LLM fallback routing, and an automated model evaluation platform (aeval) with FastAPI orchestration, Redis job queues, and statistical rigor baked into the CI/CD pipeline. These are directly relevant to Oscar's stated goal of developing product strategies for an evolving support model — specifically, deploying AI for simpler member inquiries while routing complex cases to human agents. ## Why This Role Oscar's Member Coverage & Support platform is, at its core, a data integration and workflow orchestration problem with high human stakes. Members need accurate coverage data, functioning billing and payment pipelines, and support agents equipped with tools that surface the right information at the right moment. The technical surface — APIs, integrations, legacy tooling modernization, agent-facing workflows — maps directly to the platform work I have led. What makes this role compelling is the operational consequence: a misconfigured billing workflow or a slow escalation path does not just create friction, it can delay care. That stakes profile sharpens the prioritization discipline I want to apply. I am also drawn to Oscar's explicit commitment to improving first call resolution, reducing call duration, and improving issue resolution quality through better tooling. At Intuit, I implemented ICE Presence in async chat, which generated $480,000 per month in additional invoicing — a result that came from instrumenting agent-facing workflows, measuring outcomes with telemetry and BigQuery, and iterating on the product surface based on usage data. That same loop applies directly to Oscar's support operations. ## Selected Experience Relevant to This Role - **Platform scalability at peak load:** Scaled ICE throughput from 6K to 50K TPS via rSocket migration, supporting ~1.5M concurrent connections at sub-25ms TP99 across QuickBooks, TurboTax, Mint, Mailchimp, and Credit Karma — 675M+ engagements in FY23. - **Developer and agent tooling:** Delivered ICE Self-Service platform (DevPortal, GitOps config, ICE Playground), reducing onboarding from 2–3 weeks to minutes, mitigating $1M+ in projected opex growth. - **Legacy modernization:** Initiated MSaaS Drift Detection and Resolution program — wrote a Java JAR library to scan Git repos for configuration drift, partnered with Design on DevPortal UI, and built a remediation roadmap using OpenRewrite. - **Cross-functional API and integration work:** Led Mailchimp GCP-to-AWS migration for MSaaS, delivering Golang service template, MySQL persistence integration, and updated DevPortal documentation to meet production deadline. - **Data-driven prioritization:** Used SQL and BigQuery telemetry across ~20 mobile apps and 30+ product SKUs to prioritize developer pain points; built Asterias, a declarative asset lifecycle management platform with GraphQL API. - **AI for support workflows:** Built OpenClaw multi-agent orchestration framework with gateway protocol and subagent delegation, enabling coordinated AI agent workflows — directly applicable to Oscar's model of AI-assisted triage with human escalation for complex cases. - **Regulated, operationally complex environments:** Twelve years of platform product work at Kaiser Permanente, Intuit, and Splunk — all environments with strict compliance requirements, multi-stakeholder dependencies, and high operational consequence for platform failures. - **People leadership and cross-functional execution:** Led product strategy, roadmap, and go-to-market across multiple concurrent platform workstreams at Intuit; managed cross-functional partnerships with Engineering, Design, Operations, and CTO-level stakeholders. ## Closing Oscar's mission — health insurance that works like a doctor in the family — requires platforms that are reliable, transparent, and fast enough to matter when members need them most. I have spent my career building exactly that kind of infrastructure, and I would bring to this role both the technical depth to engage credibly with engineering on complex platform tradeoffs and the product discipline to translate those tradeoffs into outcomes that members and support agents actually feel. I would welcome the opportunity to discuss how my background maps to the specific challenges your team is navigating. Sincerely, **O. Felix Amoruwa** famoruwa@berkeley.edu | 909-731-9011 | felixamoruwa.info