--- layout: default title: Jake Rosow — Resume --- # Jake Rosow West Melbourne, FL | Remote, US | 561-427-8000 | jakerosow@gmail.com Portfolio: jakerosow.com | GitHub: github.com/drshipweight | LinkedIn: linkedin.com/in/jake-rosow ## Target Roles AI Workflow Engineer · AI Implementation Engineer · Operations Tooling · Solutions Engineer, AI Workflows · AI Support Specialist ## Professional Summary AI workflow engineer with 10+ years in operations-heavy environments and a portfolio of shipped AI-assisted systems, including production business software, agent workspaces, and a daily LLM ingestion pipeline. Strongest fit for implementation-heavy AI product teams that need workflow discovery, prototyping, integration, technical documentation, QA, and support handoff for operational software where correctness and edge cases matter. I map the real workflow, write the system spec, use AI coding agents productively, and still own the architecture, review, debugging, integration details, and shipping decision. ## Selected Work ### GIFTED HQ + Gifted Academics **Two live websites, one business system** | 2026 | gifted-hq.com & gifted-academics.com - Built and integrated two production web surfaces for an operating coaching business: HQ for brand, coaching, commerce, partner paths, and operations; Academics for courses, quizzes, progress, payment plans, access, and admin. - Migrated 200+ active subscriptions from WordPress/WooCommerce into a proprietary web system without customer disruption. - Designed shared Clerk identity across separate Next.js apps and implemented Stripe webhook-driven state changes for payments, refunds, payment plans, and access changes. - Used Sanity for editable business content and Postgres for course, enrollment, progress, and payment-plan truth. ### Healthcare Support Specialist **Open-source agent workspace for health-plan CSR questions** | 2026 | github.com/drshipweight/healthcare-customer-support-specialist - Created a drop-in agent workspace that routes health-plan member questions to the right knowledge-base section, extracts verbatim source language, and drafts a CSR-ready talk track. - Structured the workflow as five staged contracts with clear handoffs, section IDs, worked example runs, and three bounded output branches: normal answer, out-of-scope transfer, or needs clarification. - Used fictional payer data and hand-authored reference material to demonstrate benefit, prior authorization, claim, and support routing patterns without PHI or proprietary plan content. ### Cost Specialist **Open-source Claude project for API cost and caching audits** | 2026 | github.com/drshipweight/anthropic-sdk-cost-specialist - Created a drop-in Claude/Codex project that audits Anthropic API usage and returns cache breakpoints, concrete code edits, before/after cost estimates per 1,000 calls, and confidence notes. - Locked the agent into four answer shapes and backed cost claims with dated reference docs for pricing, caching, usage fields, and model choice. - Built a TypeScript eval suite where Sonnet is the system under test and Opus judges shape, citations, refusals, and made-up prices; a full run costs about $0.70. ## Professional Experience ### Health First Health Plans — Rockledge, FL **Customer Care Associate** | May 2025 – Present - Handle up to 40+ member and provider calls per day while working cases inside Epic Tapestry, Microsoft 365, and internal case management tools under HIPAA requirements. - Run cases from intake to resolution, tracking requests, documentation, follow-ups, and outcomes with attention to SLA expectations and data accuracy. - Translate benefits, claims, authorizations, and questions into clear guidance for members and providers. - Identify recurring workflow problems from case volume and surface them to leadership; support peers with system navigation, escalations, and Help Desk coverage. ### GIFTED HQ **Co-Founder, COO & Product Systems Lead** | 2017 – Present - Built the software and operational backbone for a coaching business spanning commerce, course delivery, subscriptions, payments, support, marketing, and admin workflows. - Designed and shipped the GIFTED HQ and Gifted Academics web systems using Next.js, Clerk, Stripe, Sanity, Postgres, Bunny, Resend, Shippo, Upstash, and Vercel. - Migrated 200+ active subscriptions from the previous WordPress/WooCommerce setup without customer disruption. - Own day-to-day operations, product setup, customer support, content operations, and process design. - Use AI coding agents as implementation multipliers while retaining ownership of specs, architecture, review, debugging, and release decisions. ### Advanced Resources Marketing / LTC Global — Boston, MA **Director, Systems & Design** | July 2012 – February 2023 - Owned the insurance proposal workflow for multiple concurrent enterprise Employer Group and Association clients from RFP intake through data analysis and final report delivery. - Designed standardized intake, documentation, approval, and delivery workflows across carriers, agents, internal teams, and clients. - Wrote SOPs, templates, technical documentation, training materials, and workflow guides used by internal staff and partners. - Performed QA and validation across carrier data, proposal outputs, and client-facing deliverables; served as first-line IT support for office software, hardware, and networking. ### Winner Computing — Palm Beach Gardens, FL **Vice President / Technician** | August 2006 – August 2010 - Provided onsite and remote technology support for small businesses and individual clients. - Diagnosed hardware, software, networking, Microsoft Office, email, and Adobe issues. - Wrote tutorials, trained end users, logged support issues, coordinated follow-up service, and managed inventory/scheduling operations. ## Core Skills **AI Workflow and Agent Systems:** Customized Pi Coding Agent · Claude Code · Codex · prompt caching · eval design · judge models · scoped output contracts · citation-backed generation · refusal and boundary handling. **Operations Domain Experience:** healthcare support · insurance proposal workflows · Epic Tapestry · claims and benefits language · HIPAA-aware operations · underwriting workflows · admin systems. **Product and Implementation Engineering:** workflow mapping · internal tools · admin systems · business process automation · requirements translation · QA and validation · authentication · webhooks · technical documentation · user support · implementation documentation. **Web and Data Stack:** Next.js · Astro · React · TypeScript · Tailwind CSS · Clerk · Stripe · Sanity · Postgres · Prisma · Drizzle · Turso/libSQL · SQLite · Upstash Redis · Vercel · GitHub. ## Education **Northeastern University — Boston, MA** Bachelor of Science in Business Administration | Minor in Music Industry September 2010 – May 2014