Patrick Diamitani
Executive Summary
AI Forward Deployed Engineer who builds production AI systems that organizations actually run on — not demos that impress once. Architect of 16 enterprise AI systems serving 50+ daily non-technical users, with $16M+ in attributed pipeline from AI-powered automation. Published researcher (ROSTR Framework), founder of 150+ custom GPTs, and builder of 6 shipped consumer products. Fifteen years across enterprise sales (Uber, Upwork, Asana), startup leadership ($200K→$1.5M revenue), and Techstars portfolio support ($100M+ raised). I don't just build AI — I deploy it into organizations, prove its ROI, and make it stick.
Core Competencies
AI/ML Engineering
Production Systems
Forward Deployment
Domain Expertise
Professional Experience
- Architected and deployed 16 production AI systems across sales, marketing, and RevOps serving 50+ non-technical users daily — including a two-channel AI inbound system (chatbot + form automation) that attributed $9M+ in pipeline within 30 days, with a $250K deal traced to a single chat conversation.
- Built the GTM AI Platform — not one automation, but the operating system a 50-person org runs its AI adoption on: published ROSTR methodology, self-serve project intake engine, and 40+ skill library that cut idea-to-production from 4-8 hours to under 30 minutes.
- Designed and shipped an AI compliance screening system that corrected 100+ misclassified deals and more than doubled detection of ineligible opportunities — hybrid architecture with LLM interpretation + deterministic rules engine + full audit trails.
- Rebuilt a failing 4-agent post-call automation from 0/25 passing runs to fully verified production — diagnosed RAG architecture failures, pivoted to deterministic file fetch, reduced context from 882KB to 295KB while assembling 116K characters of live country data per call.
- Owned and resolved a runaway enrichment spend incident, then redesigned the system around free ICP gates and tiered cost profiles — cutting spend ~70% by architecture, not vigilance. Turned owned mistake into permanent organizational safeguard.
- Established AI governance standards: dry-run defaults, shared error handling, cost reporting on every workflow, three-tier attribution model that deliberately excluded $1.1M+ in flattering-but-false revenue for honest measurement.
- Built and shipped 6 production consumer products: LOLA (AI fitness), Replai (AI messaging), FCR Agent (credit repair), Huddle (7,000+ coworking locations), Let's Vibe AI (social connection), Artispreneur Academy (music business education).
- Created GPTPAT marketplace with 150+ custom GPTs across programming, productivity, sales, creative, civic, and lifestyle — all published in the GPT Store with real daily users.
- Founded Gency AI (AI software development consulting) and SalesGency (GTM AI consulting) — applying enterprise production discipline to client engagements.
- Published the ROSTR Framework on Zenodo (DOI: 10.5281/zenodo.19550414) — a citable architecture for production-grade multi-agent systems with PAL, RAG DAL, NPAO, and Rostr Hub components.
- Built Your48 civic intelligence platform for Chicago's 48th Ward — making local government accessible through AI-powered constituent services.
- Scaled revenue from $200K to $1.5M ARR as founding sales leader — built the sales playbook, hired and trained the team, and established repeatable enterprise motion.
- Closed enterprise accounts including Fortune 500 marketing teams seeking scalable video production solutions.
- Designed and implemented CRM automation that reduced sales cycle by 30% through intelligent lead scoring and automated follow-up sequences.
- Supported portfolio companies that collectively raised $100M+ in follow-on funding, with two successful acquisitions.
- Provided hands-on GTM support to early-stage founders on sales strategy, pitch refinement, and market positioning.
- Facilitated mentor matching and managed relationships across the Techstars network.
- Uber for Business: Closed enterprise accounts for corporate travel program, consistently exceeded quota, pioneered city-level enterprise motion.
- Upwork Enterprise: Sold workforce solutions to Fortune 1000, managing complex procurement cycles and multi-stakeholder deals.
- Asana: Enterprise work management sales, developed deep expertise in operational workflow design that informed later automation work.
- Built to $2M annual revenue producing 1,000+ live entertainment shows for 80,000+ college students across the Midwest.
- Managed P&L, vendor relationships, and 15-person event staff — full operational ownership from booking to execution.
- Developed systematic approach to event operations that scaled across multiple university partnerships simultaneously.
Publications & Research
A published, citable framework for building production AI systems. Introduces PAL (Prompt Abstraction Layer), RAG DAL (Dynamic Acquisition Layer with credibility-weighted retrieval), NPAO (5D phase taxonomy with 4D priority scoring), and Rostr Hub (four-level persistent state). Validated across 16 production systems serving 50+ daily users.
Read the paper →Complete documentation of 16 enterprise AI systems, 40+ Claude skills, and 11 production workflows — including architecture diagrams, stack details, challenges & fixes, and demonstrated ROI for each build.
View the portfolio →Shipped Products
LOLA
Replai
FCR Agent
Huddle
GPTPAT
Your48
Education
Civic Engagement
- Elected Democratic Precinct Captain serving Chicago's 48th Ward (Edgewater/Andersonville)
- Built Your48 civic intelligence platform and Leni48 campaign operations dashboard
- Apply same production discipline to civic tech — technology that serves organizing, not replaces it
Download Resume
Get a copy in your preferred format for sharing or printing.
See the Work
This resume summarizes the outcomes. The portfolio shows how it was built — architecture, stack, challenges, and fixes for every system.
View Full Portfolio →