cover_letter / art_7j3DpUQJkls

Dear Oscar Hiring Team, Oscar is doing something genuinely difficult: rebuilding health insurance from the inside out, using technology to make the experience feel less like a bureaucratic maze and more like a trusted advisor. That mission resonates with me not as an abstraction, but because the hardest product problems I have worked on — at Intuit, at Splunk, and in my own ventures — have all involved the same core challenge: making complex, high-stakes systems invisible to the people who depend on them. When a member needs to understand their bill, resolve a coverage dispute, or get fast support during a stressful moment, the platform underneath that interaction either earns trust or destroys it. I want to work on the platform that earns it. **Technical and Platform Foundation** My product background is rooted in platform infrastructure and developer-facing systems at scale. At Intuit, I owned the ICE platform — the internal compute and event infrastructure underpinning QuickBooks, TurboTax, Mint, Mailchimp, and Credit Karma. Over three years, I scaled ICE engagements 275% year-over-year to 675M+ in FY23, drove a throughput increase from 6K to 50K TPS via an rSocket migration supporting approximately 1.5M concurrent connections at sub-25ms TP99, and delivered the ICE Self-Service platform (DevPortal, GitOps config, ICE Playground) that compressed developer onboarding from two to three weeks down to minutes in pre-production and under 24 hours for production. That work required holding the full system in mind — APIs, integrations, operational workflows, and the humans on both ends — while making tradeoff decisions that balanced reliability, scalability, and developer experience. At Splunk, I owned Search Service (Go microservices), Search Catalog (a PostgreSQL metadata service), and the Splunk Processing Language (SPL/SPL2) for Splunk Cloud Services. I delivered the Scheduler Service end-to-end in approximately four months, enabling scheduled search for first-party applications, and led a query performance optimization initiative that achieved up to 10x improvements for a beta enterprise customer. I designed a repeatable RICE-based prioritization framework across three microservice backlogs, balancing internal partner, third-party developer, and Fortune 500 customer requirements simultaneously. More recently, I built production AI platforms from scratch — including a multi-agent orchestration framework (OpenClaw) coordinating workflows across real estate, insurance, health, and financial-markets domains, and a RAG retrieval pipeline with multi-provider LLM orchestration, fallback routing, structured-output validation, and token-budget optimization. These projects required the same discipline as enterprise platform work: clear API contracts, reliable integrations, and systems that degrade gracefully under load. **Why This Role** The Member Coverage & Support Platform role sits at the intersection of the two product domains I know best: complex technical platform infrastructure and the operational workflows that human teams depend on to do their jobs well. The specific challenges Oscar describes — modernizing legacy tooling, improving first call resolution, scaling through seasonal peaks, and evolving the support model to use AI for simpler inquiries while routing complex cases to human agents — are problems I have worked on in adjacent contexts and am ready to own directly in healthcare. **Role-Specific Connection** What draws me most to this role is the coverage data integrations and APIs layer. Enrollment, billing, and payment workflows are only as reliable as the data pipelines underneath them, and getting those integrations right is the kind of unglamorous, high-leverage platform work that determines whether a member's experience feels seamless or broken. I am also genuinely interested in the agent tooling challenge: building internal tools that help support teams resolve complex member issues quickly is a product problem that requires deep empathy for the agent workflow, not just the member journey. The opportunity to develop a product strategy for an evolving support model — one that thoughtfully introduces AI for routine inquiries while preserving high-quality human handling for complex cases — is exactly the kind of nuanced, operationally grounded problem I want to be working on. **Selected Prior Experience** - Delivered ICE Self-Service platform (DevPortal, GitOps config, ICE Playground), reducing developer onboarding from 2–3 weeks to minutes in pre-prod and under 24 hours for production, while mitigating $1M+ in projected opex growth — a direct analog to modernizing legacy tooling and improving platform usability for internal teams. - Achieved 275% YoY growth in ICE engagements, scaling to 675M+ in FY23; scaled throughput from 6K to 50K TPS via rSocket migration supporting ~1.5M concurrent connections with sub-25ms TP99 — demonstrating the ability to own platform reliability and scalability through high-volume, business-critical periods. - Implemented ICE Presence in async chat, generating $480K/month in additional invoicing; deployed Background-to-Foreground Messaging on iOS/Android with under 100ms latency — showing the ability to connect platform improvements to measurable business and operational outcomes. - Conducted enterprise-wide Service Language Assessment across 9 languages, analyzing usage data and developer feedback to inform strategic investment decisions presented to the CTO — demonstrating the ability to translate complex technical and operational data into clear executive narratives. - Owned Search Service, Search Catalog, and SPL/SPL2 at Splunk; delivered Scheduler Service end-to-end in ~4 months and led query performance optimization achieving up to 10x improvements — establishing a track record of shipping complex platform products on deadline with measurable results. - Built Vantage's 40+ agent tool backend (FastAPI, SSE streaming, async job polling, idempotent endpoints) and OpenClaw multi-agent orchestration framework with gateway protocol and subagent delegation — directly relevant to designing AI-augmented support workflows that route inquiries intelligently between automated and human handling. - Led Mailchimp GCP-to-AWS migration for MSaaS, delivering Golang template, MySQL persistence integration, and updated DevPortal documentation to meet production deadline — experience managing cross-functional platform migrations with hard operational deadlines. **Closing** Oscar's mission — health insurance that behaves like a doctor in the family — depends on getting the invisible infrastructure right. Members should never have to think about coverage data integrations or billing workflows; they should just get answers and resolution. Building the platform that makes that possible, at the scale and complexity Oscar operates, is work I am ready to lead. 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