Shawn Cunningham
Current AI work: Agentic automation →

High-Velocity Problem Solving.

Discover → Build → Deploy → Iterate. From the first portable audio device to real-time trading platforms to AI-driven agentic systems.

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About

Principal Engineer & Fractional CTO based in San Francisco

for·ward de·ployed /fôr-wərd di-ploid/ adj.

1. Embedded directly with the customer. Operating at the intersection of complex business problems and production-grade engineering. Taking systems from zero to scale through first-principles problem solving.

I've spent 25+ years at the frontier of every major tech wave — early internet, e-commerce, real-time financial systems, healthcare IT, legal tech, and now applied AI and agentic orchestration. The constant: turning ambiguous, high-stakes problems into systems that ship and hold up under load.

Whether it's building a HIPAA-compliant messaging platform, designing the transaction engine for the world's first betting exchange, or wiring up LLM-driven workflows in production, I bring CTO-level thinking with hands-on-keyboard execution.

Career Timeline

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AI & Enterprise Era — 2016–Present
2022 – Present
Lead Software Engineer
BigHand
75% code / 25% manage · 3 reports

Ported data processing SaaS into an embeddable microservice. Migrated AWS to Azure for SOC2 compliance. Built expert system for legal timesheet categorization saving clients hundreds of thousands.

  • Ported data processing SaaS application into an embeddable microservice within an existing platform
  • Migrated system from AWS to Azure, aligning with enterprise infrastructure requirements (SOC2)
  • Developed expert system for categorizing improperly categorized timesheet data
  • Enabled integration into larger workflow systems, improving scalability and operational flexibility
2016 – 2022
CTO
Digitory LegalAcquired by BigHand
60% code / 40% manage · 5 reports

Built multi-tenant SaaS platform for legal budgeting and spend management from zero. Led discovery with legal & finance stakeholders. Built data ingestion and normalization pipelines.

  • Built multi-tenant SaaS platform for legal budgeting and spend management
  • Led discovery with legal and finance stakeholders to model workflows and decision systems
  • Built data ingestion and normalization pipelines integrating external billing systems
  • Operated production system with focus on reliability, auditability, and secure handling of sensitive data
Consultancy Era — 2004–2016
2004 – 2016
Founder & CTO
Layer 3 Development
25% architect / 45% code / 30% manage · 8 reports

Boutique consultancy. 20+ client engagements across fintech, legal tech, hospitality, real estate, consumer apps, and IoT/energy. Discovery to production to scale.

CNE Media · Prosper · Springboard Auto · Integreon · Shangri-La Hotels · The Melt · Prometheus · Chefs Feed · Geli
  • Sole revenue driver — sourced, scoped, and delivered every engagement end to end, from discovery through production and account growth
  • Built distributed SaaS platforms, APIs, and data pipelines across finance, healthcare, legal tech, real estate and e-commerce
  • Architected high-volume video production, large-scale encoding farm, and global CDN-backed distribution platform for CNE Media (online video network)
  • Integrated automation and AI-style workflows for data extraction, classification, and decision support
  • Designed scalable SaaS messaging architectures for decoupled, event-driven systems
  • Migrated and operated systems on AWS, improving deployment speed and system reliability
Dot-Com & Healthcare — 1996–2004
2001 – 2004
Chief Software Architect
RelayHealthAcquired by McKesson
50% architect / 50% code

Architected HIPAA-compliant messaging and e-prescribing platform. Built secure Java/C# backends supporting provider-patient workflows and regulatory compliance.

  • Led development for secure, HIPAA-ready, doctor-patient communication services
  • Architected NCPDP Script Standard based B2B electronic prescription hub for NDCHealth
  • Ported ASP/COM+/SQL application to C# .NET for scalability and code reuse
  • Managed engineering team downsizing and retooling to meet budgets and refocus skills
2000 – 2001
CTO
Flutter.comIPO 2010
25% architect / 50% code / 25% manage · 25 devs

Built the world's first online betting marketplace. $39M from Benchmark, Index Ventures, UBS Capital. Merged with Betfair to create the world's largest exchange betting company.

  • Led design and development of the world's first online betting marketplace
  • Participated in $39M private equity financing from Benchmark Capital, Index Ventures, Chase, UBS Capital
  • Architected highly scalable real-time transaction processing on Java/J2EE, WebLogic, Oracle, Solaris
  • Designed and deployed a $2.5M data center at Exodus London for 24/7 availability
  • Grew and managed 25 high-output developers; merged with Betfair in Dec 2001
1997 – 1999
CTO
CookExpress.comFirst of its kind

Built the world's first internet-based gourmet same-day meal delivery service. End-to-end: e-commerce, credit card processing, JIT manufacturing, logistics, same-day distribution.

  • World's first internet-based gourmet pre-prepared same-day meal delivery
  • Designed all mission-critical systems from front-end to back-end
  • E-commerce, credit card processing, just-in-time manufacturing, logistics, distribution
  • Launched same-day in San Francisco, then national overnight delivery
1996 – 1997
Technical Director
AudioHighway.comPre-iPodIPO 1998

Built the first portable downloadable audio device — a predecessor to the iPod. Won CES 1997 Most Innovative Product of the Year.

  • Designed and developed an innovative internet audio distribution system with portable device
  • Architected dynamic database-driven web-based audio library for device downloads
  • Designed the AudioWiz client software for content management and device sync
  • Won the 1997 Consumer Electronics Show Most Innovative Product of the Year Award
Engineering Roots — 1992–1996
1994 – 1996
Technical Director
SoftAdFord's first web presence

Established Internet division. Built Ford Motor Company's first website, generating $1.5M+ in internet business. Integrated legacy systems with online vehicle configuration.

  • Established Internet division responsible for Ford Motor Company website
  • Generated over $1.5M in Internet business
  • Integrated Ford's legacy and Internet systems for online vehicle specs and pricing
  • Set standards for development across the practice
1992 – 1994
Controls Engineer
Berkeley Process ControlAcquired by Moog 2008

Pioneered combining digital precision encoders with brushless servo motors to create a new class of precise motion control systems. Deployed across wafer fab, fiber optic cable manufacturing, airframe optimization, and trans-oceanic oil pipeline construction.

  • Custom, real-time, multitasking machine control software and hardware applications
  • Designed a line of custom Brushless Servo Motors for 64-bit RISC Machine Controller
  • AT&T Bell Labs High Speed Fiber Optic Winding Draw Tower
  • Boeing Airframe Weight Optimizer
  • McDermott Trans-Oceanic Pipeline Welder
Companies & Clients
Flutter / Betfair•McKesson / RelayHealth•Ford Motor Company•Prosper Marketplace•Shangri-La Hotels•The Melt•Chefs Feed•Prometheus Real Estate•Geli / Hanwha Energy•Springboard Auto•Integreon

Expertise

Core competencies across three decades of building production systems

Embedded Engineering

Customer-embedded delivery. Discovery through production through iteration, operating inside complex enterprise environments with first-principles problem solving.

AI & Agentic Systems

LLM integration, agentic orchestration, multi-agent systems, workflow automation. Production AI pipelines with Claude Code, Codex, Ollama, and custom frameworks.

Distributed Systems

Real-time transaction processing, SaaS, messaging architectures, command & control platforms, telemetry systems, and 24/7 production operations.

Security & Compliance

HIPAA-compliant healthcare systems, SOC2 enterprise migrations, secure handling of sensitive legal and financial data, and audit-ready production environments.

Data Engineering

Ingestion pipelines, normalization engines, ETL at scale, data classification systems. Multi-tenant architectures with PostgreSQL, MongoDB, and SQL Server.

CTO & Technical Leadership

Strategy, roadmapping, team building, investor presentations. Scaled teams from 3 to 25. Multiple acquisitions and IPOs. Technical due diligence and advisory.

Technology

Languages, platforms, and tools across the full stack

Languages
PythonRubyC#JavaJavaScript / TypeScriptSQLGoRust
Frameworks & Frontend
ReactElectronNode.jsRails.NETJ2EE
Cloud & Infrastructure
AWS (EC2, S3, Lambda, RDS, CloudFront)AzureCloudflareHerokuCI/CDDocker
Data & Messaging
PostgreSQLMySQLSQL ServerMongoDBRabbitMQZeroMQ
AI & Agentic
Claude CodeCodexGeminiOllamaHugging FaceLLM OrchestrationMulti-Agent Systems

Education

B.S. Mechanical Engineering
University of Rhode Island
Tau Beta Pi Engineering Honor Society
Professional Certificate — ML & AI
UC Berkeley College of Engineering

Mechanical engineering foundation with deep cross-training in software systems, machine learning, and applied AI. The ME background shows up everywhere — from designing brushless servo motors at BPC to building mechanical drive systems for large-scale kinetic sculptures.

Beyond Software

Large-Scale Kinetic Sculpture

Where mechanical engineering meets public art. I design and develop the mechanical drive systems for large-scale, public kinetic sculptures — pieces that move, breathe, and respond to their environment.

This is where the ME degree from URI meets decades of systems thinking: precision gearing, load analysis, environmental tolerances, and the same reliability engineering that goes into production software — applied to steel, motors, and motion at architectural scale.

Mechanical Drive SystemsPrecision GearingPublic InstallationArchitectural ScaleEnvironmental Design
Watch the Sculpture in Motion

Get In Touch

Available for fractional CTO engagements, forward deployed engineering, and technical advisory

Location
San Francisco, CA