Ashkaan Hassan, Esq.

AI Systems Architect

I've spent the last year building production AI systems that run real businesses. Now I want to build them for yours.

LVL 14
AI Systems Architect

14 yrs XP · Ready for next level

About

Over the past year, I've built an AI-native operating system for my businesses—50+ production automations orchestrated by Claude, managing everything from client onboarding to financial reporting to infrastructure monitoring. Every piece ships, every piece runs, every piece compounds.

The platform runs on Windmill with Claude Code at the center. Governance rules, delegation routing, context management, session memory—all codified and enforced automatically. It's not a demo; it's how I run two companies every day.

My background spans law, technology, and business leadership. What unites it all is a drive to build systems that compound.

I'm looking to bring this builder's mindset to Anthropic as a Forward Deployed Engineer—helping enterprise customers build the production AI systems that transform their operations.

Ask About My Experience

Powered by Claude — ask anything about my background, projects, or skills.

Contextium

Open-Source AI-Native Knowledge Management

Contextium is the operating system behind everything on this page. It's an open-source framework for AI-native personal knowledge management — file-based context routing, governance rules, structured memory, and session management. Every project, every automation, every decision in my workflow is orchestrated through this system. It's not a demo — it's how I actually work, every day.

Context Router

Lazy-loads relevant knowledge based on task triggers. AI sessions only see what they need.

Governance Rules

Behavioral rules, credential policies, session protocols. Enforced automatically across all AI sessions.

Structured Memory

File-based memory system that persists across conversations. People cards, project trackers, growth goals.

Context Router in Action

Select a task type to see which context files get loaded.

All Contexts

integrations/komodo/README.md
projects/README.md
rules/behavior.md
rules/governance.md
rules/incident-response.md
style_guides/app-development.md
style_guides/code-conventions.md
style_guides/email_templates.md
templates/edge-app/
templates/project_template.md
windmill/README.md

Loaded

windmill/README.md
rules/governance.md
rules/behavior.md
style_guides/code-conventions.md
View on GitHub

What I've Built

Production systems running real businesses, every day.

AI Agent Orchestration

Windmill-based platform managing 50+ production automations. Claude Code hooks enforce governance, delegation rules route tasks to specialized agents, and session management preserves context across conversations.

production

Enterprise AI Audit Framework

178-control assessment methodology for enterprise IT. Covers security, compliance, and AI readiness. Currently deployed at MannKind Corporation.

production

AI Operations Product

Full lifecycle: Assess > Build > Operate. Playbook, sales guide, assessment tool, build standards, operational runbook. Productized AI service delivery for enterprise customers.

production

Finance Portal

Real-time financial dashboard — revenue tracking, contract lifecycle, payroll analysis. Astro + React + Cloudflare KV with SSE live updates.

production

Operations Portal

Workforce management dashboard — attendance auditing, DNS compliance monitoring, travel billing, SLA tracking. Automated data pipelines via Windmill.

production

Sales Portal

Pipeline management and CRM — prospect research, communication tracking, SDR workflow automation.

active

Infrastructure Automation

Proxmox cluster, TrueNAS, Docker fleet managed via Komodo. Aegis monitoring system runs 15+ automated health checks with drift detection and self-healing.

production

Experience

We Solve Problems

Founder & CEO

2011 – Present
  • Built from zero to $1.09M ARR over 14 years, 25+ managed clients, 6-person team
  • Pivoting from traditional MSP to AI-first operations company
  • 40% SDE margin — 2x industry average

Radius Agent

Chief Compliance Officer

2017 – 2023
  • Real estate technology platform serving 70,000+ agents nationwide
  • Regulatory compliance, legal frameworks, operational risk management

Marvel Studios

IT Systems Consultant

2016
  • Overhauled networking and storage infrastructure for Thor: Ragnarok production on Gold Coast, Australia
  • Solutions became Marvel's IT gold standard for future productions

Nu|Legal

Principal Attorney

2012 – Present
  • Boutique law practice in Beverly Hills
  • Business law, real estate transactions, compliance advisory

We Solve Problems

14 Years Building a Technology Company

$0M
Revenue
0+
Managed Clients
0
Team Members
0%
SDE Margin (2x industry avg)

I founded WSP in 2011 as a one-person IT consultancy. Over 14 years, I built it into a managed services company serving 25+ clients with a 6-person team. The past year has been a transformation — pivoting from traditional IT support to AI-first operations, building the automation platform that now runs the business.

2011Founded WSP
2012
2016
2017
2023
2025
2026

Why this matters for Anthropic

  • Built and deployed 50+ production Claude automations managing real business operations
  • Enterprise AI audit framework used with Fortune 500 clients
  • Hands-on experience with the exact problem FDEs solve: helping organizations adopt AI

Skills & Tools

TypeScriptPythonDockerProxmox VECloudflare Workers/Pages/KVAstroReactTailwindWindmillAI/ML SystemsClaude API/SDKCoreGitLinuxZFS/TrueNASHome Assistant
DEF CON attendeeEliteSOC 2 complianceCIS Controls178-control audit frameworkMSSP operations
CloudflareGitHubWindmillAutotaskNinjaOneQuickBooksKomodo

Leadership & Community

After-School All-Stars LA

Board Chair (current)

Youth development nonprofit providing free comprehensive afterschool programs.

Entrepreneurs' Organization (EO)

6 leadership roles

Engagement Co-Chair, Learning Co-Chair (incoming), Forum Co-Chair, Finance Chair. 4+ years of chapter leadership.

CA Commission on Judicial Nominees Evaluation

Commissioner

Evaluating judicial candidates for the State Bar of California.

Games for Love

Advisory Council

Gaming charity focused on hospitalized children.

Education & Credentials

Juris DoctorDegree

University of San Diego School of Law (2008 – 2011)

B.S. Business LawDegree

California State University, Northridge (2003 – 2008)

Minors: Metaphysics, Psychology. Started in Astrophysics.

Certified Kubernetes Administrator (CKA)Certified

Cloud Native Computing Foundation

California State BarLicensed

Active member #381138 (admitted 2012)

CA Real Estate BrokerLicensed

Active license (since 2014)

Mortgage Loan OriginatorLicensed

NMLS (Federal + CA, 2014)

Certified MediatorCertified

National Conflict Resolution Center (2009)

Google Workspace AdministratorCertified

Google (2019)
FDE Fit

FDEs embed with enterprise customers to build production AI systems. That’s exactly what Ashkaan does — just for his own companies.