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Barry Pilgrim

Software Engineer

Lifelong technologist. 20+ years writing and maintaining enterprise software. Now I build end to end with AI agents in the loop. I ship systems for web and desktop, including AI-native applications.

The AI is why I can deliver fast. My engineering background is why the work holds up.

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20+ yrs
Shipping enterprise software
8 industries
Banking to retail operations, government to digital marketing
1,000+
Users on the platform I led, across 130+ offices
Daily
AI agents I actually run — not demos

Experience

25+ years · 8 companies
  1. 2024 — Present

    Software Engineering & AI Systems · Independent Consultant

    Building complete products solo: AI agents in daily production use, desktop applications, and the business systems small companies actually run on. This site and the assistant answering questions on it are part of the same body of work.

    • TypeScript
    • Python
    • Claude API
    • .NET
    • Cloudflare Workers
  2. 2020 — 2024

    Technical Lead · Veritext Legal Solutions

    Led a distributed team of four on Vision, a mission-critical legal operations platform serving 1,000+ users across 130+ offices. Architected the WebView2 bridge that let a monolithic WPF application migrate to React incrementally — no big-bang rewrite, no operational downtime.

    • C#
    • WPF / MVVM
    • WebView2
    • SQL Server
    • GraphQL
    • Camunda
  3. 2018 — 2020

    Senior Developer · Bank of America

    Merrill Guided Investing — a customer-facing investment platform built under strict financial-compliance constraints. Worked within SAFe across 8–10 coordinated teams in the U.S. and India; served as designated backup Technical Lead.

    • ASP.NET
    • JavaScript
    • WCF
    • REST
    • SOA
  4. 2012 — 2018

    Senior Developer · Vertican Technologies

    vExchange, a B2B data integration platform moving secure operational data between banks, law firms, and collections agencies. Built and maintained the NextGen API layer alongside a suite of enterprise .NET applications.

    • C#
    • .NET
    • SQL Server
    • IIS
    • Angular
    • ServiceStack
  5. 2010 — 2012

    Senior Developer · IDT Corporation

    BOSS Revolution, a high-volume international calling and retail telecom platform used by distributors, retailers, and end customers worldwide.

    • C#
    • ASP.NET
    • SQL Server
  6. 2007 — 2009

    Senior Application Developer · Zeta Interactive

    Zeta Buzz, a social-media data-mining platform ingesting 50,000+ blogs and 500,000+ posts a day through a distributed, multi-threaded collection architecture. Raised throughput 25% per instance and cut new-source onboarding time by 75%.

    • VB.NET
    • C#
    • XML
    • RegEx
    • Multi-threading

Earlier: Lead Developer at SGW · BCT Partners · consulting for BMW of North America, Gucci Group, Cendant, and Wakefern Food Corporation.

Selected work

All projects →
Flagship

Vision · Enterprise Legal Operations Platform

Technical lead on a mission-critical platform serving 1,000+ users across 130+ offices — and the migration bridge that let it modernize without going down.

C# · WPF (MVVM) · WebView2 · SQL Server · WCF · GraphQL · Camunda · Amazon S3 · SSRS · Datadog

  • Desktop
  • Web

AI Assistant

A capture system with no rules engine. Send it anything from your phone; a language model decides what it is and files it. In daily use.

Python 3.12 · Anthropic Claude · Model Context Protocol · Telegram · Google Calendar/Gmail APIs · hexagonal architecture

  • AI
  • Automation

A File-Based Workspace for AI

Most AI work starts from zero every session. This is the opposite bet: no database, no framework, no agent runtime — the folder is the app.

Markdown · YAML frontmatter · Obsidian · Claude Code · ~30 packaged skill workflows

  • AI

What I do

Through Software On-Demand, I build custom software for process-driven small businesses — the CRM, tracker, dashboard, or automation that a company is currently running on a spreadsheet and goodwill. Discovery to deployed, by one person who has done this at enterprise scale.

How it works →

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