Portfolio · 2026

AI workflow engineer for complex operations.

I build AI-assisted workflow tools for teams where correctness, auditability, integrations, and edge cases matter.

Portrait of Jake Rosow
Jake Rosow
Status
Open to roles
Based
Remote · US · Melbourne, FL
Education
Northeastern '14 · BSBA
01 — Selected Work

Selected work.

Case studies on the deeper builds: product screens, system shape, the decisions worth defending, and what it cost to make those calls.

02 — Best Fit

Where I fit.

Best fit

  • AI workflow engineering for operations-heavy product, support, and implementation teams.
  • Internal tools, agent workspaces, workflow automation, and productized demos.
  • Solutions or implementation engineering where workflow judgment matters as much as code.

Less useful for

  • Pure frontend-only roles.
  • Research-only AI roles with no shipped workflow surface.
  • Generic CRUD app work without messy operational constraints.
03 — Operating Model

How I build.

01

Map the real workflow

Start from who actually does the work, who pays, who audits, and what breaks if you get it wrong. The tool choice comes last. The system will reflect the org chart whether you wanted it to or not, so it's better to do that on purpose.

02

Spec the system

A markdown vault holds the data models, service boundaries, edge cases, and known failure modes. That same vault is the prompt context for every agent run. If it isn't written down, the agent doesn't know it.

03

Ship with agents

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

agent work

How I work with agents.

I own the shape

I write the workflow model, data boundaries, acceptance criteria, and failure cases before the implementation run.

Agents accelerate implementation

Claude Code handles a lot of code production. I steer the architecture, review diffs, debug integrations, and decide what ships.

Evidence beats vibes

For AI features, I look for citations, scoped outputs, eval cases, cost visibility, and recovery paths before polish.

04 — Experience

Where I’ve been.

2017 — now
GIFTED HQ
Co-Founder, COO & Director of Administration

Built a coaching SaaS from scratch: a Next.js commerce site and an Expo mobile app sharing one Clerk identity, on Stripe, Sanity, Supabase, Bunny, Resend, and Shippo. Made the calls on shared web/mobile auth and the webhook-driven Sanity→Stripe sync. Migrated the old WooCommerce storefront without losing SEO, accounts, or order history. Also run the day-to-day business: subscriptions, payments, support, marketing.

2025 — now
Health First Health Plans
Customer Care Associate

Work member and provider cases inside Epic Tapestry, Microsoft 365, and our case management tools, under HIPAA. Track service requests from intake through close, flag the recurring workflow issues to leadership instead of just absorbing them, and back up the Help Desk on escalations and system questions.

2012 — 2023
LTC Global / Advanced Resources Marketing
Director, Systems & Design

Owned the insurance proposal workflow end to end for enterprise Employer Group and Association clients: RFP intake, data analysis, final report. Coordinated documentation and approvals across carriers, agents, and internal teams in CRM and Asana. Built the SOPs and templates the team actually ran on. Doubled as first-line IT for software, hardware, and networking.

2006 — 2010
Winner Computing
Vice President / Technician

Diagnosed hardware, software, and networking issues for end users, on site and remote. Wrote the tutorials and ran the trainings on Microsoft Office, email, and Adobe. Handled IT inventory, company assets, scheduling, and payroll.

05 — Background

About Jake.

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

That background is the part I'd actually bet on. I'm not trying to look like a generic AI builder. What I'm good at is taking messy, integration-heavy operational workflows and turning them into software a hiring team can inspect in an afternoon and trust.

Concretely: judgment about what to build vs. what to buy, a feel for where systems quietly fall apart under real load, and the habit of writing the spec before the code. Claude Code is a multiplier on top of that. It isn't a substitute for any of it.

06 — Contact

If your team wants someone who actually ships, let’s talk.