~/jakerosow.com—v2.0.0—last_deploy: 2026.05.02

I build pragmatic AI tools

Jake Rosow — staff-level builder. I architect, integrate, and ship complete systems with AI coding agents, grounded by 10+ years in insurance and healthcare operations. Currently looking for senior IC roles at AI-native companies.

→ see selected work$ contact ↗$ experience
Status
● open to roles
Based
remote · US
Stack
TS · Python · Postgres
Shipped
3 prod systems / yr
// 01Selected Workn=4 · sorted by recency
01gifted-platform.saasCoaching SaaS — Next.js, Expo, Clerk, Stripe, Sanity, Supabase, Bunny, Resend, Shippo. Live commerce, shared web/mobile auth.TS · Next.js · Expo · Stripe● live02shipit-news.pipelineMulti-source AI/coding news aggregator — model routing, prompt caching, idempotent ingestion, run-level cost tracking.Python · Postgres · Anthropic · OpenAI○ in-progress03claims-translator.healthcareHealthcare/insurance workflow demo — translates 10+ years of operations experience into a linkable product proof.TS · LLM · FHIR · X12○ queued04vault-specs.internalLiving specification system feeding Claude Code — vault-backed, MCP-compatible, drives every project I ship.Markdown · MCP · Claude Code○ internal
// 02Case Study / gifted-platformopen · 9min read
flagship case study

GIFTED — coaching SaaS, end-to-end

A complete coaching ecosystem: Next.js commerce + content site paired with an Expo mobile app for training programs, nutrition tracking, video check-ins, and messaging. Replaced Trainerize, TrueCoach, WhatsApp, Sheets, Drive, and WooCommerce with one product.

STATUS
HQ live · mobile in dev
SOURCE
private
STARTED
late 2024
ROLE
architect + integrator
HQgifted-hq.com
  • Next.js · Sanity CMS
  • Clerk auth · Stripe
  • Bunny CDN · Resend
  • Shippo · Supabase
MOBILEExpo
  • Fastify backend
  • Reads Clerk metadata
  • Supabase realtime
  • GROQ → coach profiles
STRIPEsingle source of truth for $$$

// why it exists

A coaching business needed to consolidate Trainerize, TrueCoach, WhatsApp, Google Sheets/Drive, WooCommerce, and ad-hoc file delivery into one platform the business actually owns.

HQ handles subscriptions, commerce, coach profiles, consultations, and CMS-owned content. Mobile gives coaches and clients one delivery surface for programs, nutrition, video check-ins, bloodwork files, and messaging.

// what made it hard

Two surfaces sharing auth + subscription state. Stripe webhook reliability is non-negotiable because real charges flow through it. Coach profiles must be editable without developer help. Training videos and bloodwork PDFs need signed URLs and access control. Coaching is messaging-heavy, so real-time delivery matters.

// pragmatic decisions

01
Cart sync via Clerk metadata, not a cart service
choseCart state lives in Clerk user unsafeMetadata; localStorage is the fast path with a 1.5s debounce.
whyCross-device persistence without a Redis/db cart service before scale demands it.
costClerk metadata size limits; hard refreshes during the debounce window can lose the last edit.
02
Sanity drives Stripe, not the other way around
choseA Sanity webhook triggers a Next.js route that syncs coach products into Stripe as a downstream cache.
whyBusiness edits content in one place; no Stripe-dashboard drift.
costWebhook reliability, partial failures, out-of-order updates become product-critical.
03
One Clerk app across web and mobile
choseHQ handles Stripe webhooks, writes subscription state to Clerk publicMetadata; mobile reads the same identity.
whySingle sign-in and one subscription source of truth across the ecosystem.
costWeb and mobile become deliberately coupled around auth and subscription state.
Next.js App RouterTypeScriptExpoFastifyClerkStripeSanitySupabase PostgresBunny CDNResendShippoSupabase RealtimeTurborepoClaude Code
// 03Processarchitecture-first · agents-second · verification-always
PHASE 01

Map the real workflow

Start from the operator, customer, compliance, and revenue constraints — not the tool choice. The system reflects the org chart whether you want it to or not.

PHASE 02

Spec the system

Living vault documents data models, service boundaries, edge cases, and failure modes. Becomes the prompt context for every agent run.

PHASE 03

Ship with agents

Claude writes most of the code. I drive architecture, review diffs, debug integrations, and decide what ships. The acceptance bar stays mine.

// 04Backgroundops taste, applied to AI-native building
portrait.jpg
Jake Rosow

10+ years in insurance and healthcare operations. Underwriting workflows, claims pipelines, broker tooling, compliance edges. The kind of domain where the edge cases are the product.

That background is the unfair advantage. I'm not trying to look like a generic AI builder. The leverage is translating messy, integration-heavy, regulated workflows into reliable software hiring teams can inspect quickly.

What I bring: judgment about what to build vs. buy, instinct for where systems fail under real load, and a habit of writing specs before code. Claude Code is a multiplier on top of all of that — not a replacement for it.

// 05Experience$ git log --reverse --pretty=oneline
2017 — now
Co-Founder, COO & Director of Administration @ GIFTED HQ
Architected and shipped a coaching SaaS with a unified Next.js commerce site + Expo mobile app on Clerk, Stripe, Sanity, Supabase, Bunny, Resend, and Shippo. Drove the technical decisions — hybrid web/mobile auth, webhook-driven Sanity→Stripe sync. Migrated the legacy WooCommerce storefront without losing SEO, accounts, or order history. Run daily business ops: subscriptions, payments, support, marketing.
2025 — now
Customer Care Associate @ Health First Health Plans
Resolve member and provider cases across Epic Tapestry, Microsoft 365, and proprietary case management while maintaining HIPAA, data accuracy, and compliance standards. Track service requests intake-to-close, surface recurring workflow issues to leadership, and back up the Help Desk on escalations and system navigation.
2012 — 2023
Director, Systems & Design @ LTC Global / Advanced Resources Marketing
Owned insurance proposal workflows end to end for enterprise Employer Group and Association clients — RFP through data analysis through report generation. Coordinated documentation and approvals across carriers, agents, and internal teams in CRM and Asana. Built the SOPs, templates, and standardized workflows the team ran on. Doubled as first-line IT for software, hardware, and networking.
2006 — 2010
Vice President / Technician @ Winner Computing
Diagnosed hardware, software, and networking issues for end users on site and remotely. Trained users on Microsoft Office, email, and Adobe through written and in-person tutorials. Managed IT inventory, company assets, staff scheduling, and payroll.
// 06Contactresponse time: < 24h
$whoami
jake rosow — staff-level builder, ops-first, agent-native
$looking_for
senior IC / staff role at an AI-native company

If your team needs someone who ships — let's talk.

→ hello@jakerosow.com$ github ↗$ linkedin ↗