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.
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.
The FDE role is where my skills converge. I've spent 14 years translating complex technology into business outcomes for clients—first as an attorney advising on tech compliance, then as a CEO building and deploying IT solutions. I've lived the enterprise customer journey from the inside. And for the past year, I've been doing exactly what an FDE does: building production systems on Claude's platform, shipping them to real users, and iterating based on what actually works. The difference is I've been doing it for my own companies. I want to do it for Anthropic's most important customers.
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.
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.
Enterprise AI Audit Framework
178-control assessment methodology for enterprise IT. Covers security, compliance, and AI readiness. Currently deployed at MannKind Corporation.
AI Operations Product
Full lifecycle: Assess → Build → Operate. Playbook, sales guide, assessment tool, build standards, operational runbook. Productized AI service delivery for enterprise customers.
Finance Portal
Real-time financial dashboard — revenue tracking, contract lifecycle, payroll analysis. Astro + React + Cloudflare KV with SSE live updates.
Operations Portal
Workforce management dashboard — attendance auditing, DNS compliance monitoring, travel billing, SLA tracking. Automated data pipelines via Windmill.
Sales Portal
Pipeline management and CRM — prospect research, communication tracking, SDR workflow automation.
Infrastructure Automation
Proxmox cluster, TrueNAS, Docker fleet managed via Komodo. Aegis monitoring system runs 15+ automated health checks with drift detection and self-healing.
Experience
We Solve Problems
Founder & CEO
- 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
- Real estate technology platform serving 70,000+ agents nationwide
- Regulatory compliance, legal frameworks, operational risk management
Marvel Studios
IT Systems Consultant
- 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
- Boutique law practice in Beverly Hills
- Business law, real estate transactions, compliance advisory
We Solve Problems
14 Years Building a Technology Company
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.
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
Technical
Cybersecurity
Platforms
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 Doctor
University of San Diego School of Law (2008 – 2011)
B.S. Business Law
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 Broker
Active license (since 2014)
Mortgage Loan Originator
NMLS (Federal + CA, 2014)
Certified Mediator
National Conflict Resolution Center (2009)
Google Workspace Administrator
Google (2019)
FDEs embed with enterprise customers to build production AI systems. That's exactly what Ashkaan does — just for his own companies.