Cole Ciprari

Business Systems Architect · Complex Business Systems, Operations Technology & AI Automation
Worcester, MA 01608 · cole@ciprari.ai · (508) 688-5824 · linkedin.com/in/coleos · download PDF

SUMMARY

Systems architect who designs the architecture and ships the code. 15+ years architecting complex business systems — enterprise project and portfolio platforms, ERP/POS integrations, RPA pipelines and AI-augmented workflows — plus 20 production platforms built solo, including a 120-route construction ERP and a multi-tenant SaaS estimating suite serving 25+ trades. Owns the full lifecycle: requirements discovery, platform evaluation, integration and data-model design, build, migration, training and post-launch adoption measurement. 70% of manual data entry eliminated, 250+ labor hours reclaimed annually, 18% schedule variance reduction, with P&L accountability for portfolios up to $8.5M.

PLATFORMS BUILT AND SHIPPED SOLO

Every platform with a public site is monitored live on the public status page.

EXPERIENCE

Edgeball Strategies — Director of Media & Intelligence (contract)
Oct 2026 – present · Remote

Runs Edgeball's publishing operations and commercial partnerships. Wheels Car Rental System is the anchor sponsor of The Edgeball Edge. The newsletter reaches thousands of fleet, rental and dealer loaner operators.

Edgeball Strategies — Editor in Chief, The Edgeball Edge (contract)
Sep 2026 – present · Remote

Editor in Chief of The Edgeball Edge, Edgeball Strategies' LinkedIn newsletter for fleet, rental and dealer loaner operators: operational intelligence from Edgeball's Deal Desk, written as blueprints rather than thought leadership.

Ciprari.AI — Founder
Aug 2026 – present · Remote

Founder of Ciprari.AI, the practice behind ciprari.ai: ColeOS, a résumé built as a working retro operating system with an AI assistant, an App Builder and a Job Fit Analyser, plus changelog.ciprari.ai, a build log that writes itself.

Coen Construction — Project Portfolio Manager
Oct 2025 – present · Worcester, MA

Systems & AI architecture for an $8.5M project portfolio; sole architect and engineer of the company's 120+ route ERP covering estimating, payroll, payments, telephony and field operations.

Hannaford Bros. Co. — Evening Operations Manager
2025

Performance systems architecture across 10 departments; audit score 88 → 96; 250 labor hours reclaimed.

Andyman Dessert Baking Co. — Operations Manager
2023 – 2024

POS/inventory/finance integration architecture; 70% of manual entry eliminated; inventory turns +12%, waste −9%, revenue +18%.

Naples Pizzeria — Managing Partner
2020 – 2023

$1.2M P&L; revenue $650K → $900K; cloud HR stack; hiring 10 days → 3; turnover −35%.

TSD Rental, LLC — Operations Manager / Strategic Planning Lead
2014 – 2020

Two facilities, $1M assets at 98% utilization; IT infrastructure and multi-site systems architecture; $30K/yr contract savings.

Liberty Mutual Insurance — Operations Process Improvement Specialist
2010 – 2014

RPA across claims: errors −15%, cycle time −22%; enterprise knowledge architecture of 200+ processes for 3,000+ users at >99.9% uptime.

Early career
2002 – 2009

Exsos LLC (senior account executive, IT staffing — built the TD Banknorth pipeline through the Commerce Bank merger); Technology Seed (contract IT support — Windows Server, Exchange, Active Directory, Cisco); Datamonitor ($275K+/quarter enterprise sales in healthcare/pharma — Pfizer, AstraZeneca, Stryker); Bad Boy Entertainment & Sean John Clothing (marketing/promotions and artist logistics).

CERTIFICATIONS

Claude Code Certified (Anthropic) · OpenAI Certified Architect (OpenAI). In progress: Google Cloud Generative AI Fundamentals, Google Analytics 4, Automation Anywhere RPA Essentials.

Prefer the live demo? The interactive version of this résumé is a working operating system: boot ColeOS → Or read answers to common questions.
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