Shawn Cunningham

CTO & Forward Deployed Engineer.

Discovery → Build → Production → Iteration. From the first portable audio device to real-time trading platforms to AI-driven agentic systems.

Principal Engineer & Fractional CTO · San Francisco, CA · connect@layer3dev.com · Book a 15-min intro

About

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

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 Legal Acquired 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

RelayHealth Acquired 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.com IPO 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.com First 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.com Pre-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

SoftAd Ford'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 Control Acquired 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

Forward Deployed 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
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

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.

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