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Jack HolowczakJH

Jack Holowczak

Fractional CTO | AI & Supply Chain

€1,924/day
Toronto, CA
8-15 years

Average response time: 1 hour

About Jack

Toronto-based Executive Chairman & Operations Architect


I bridge the gap between "Bay Street" private capital rigour and technical innovation.

As a Dual-Threat Executive (Capital Markets + AI Engineering), I help Private Equity firms and Canadian enterprises solve complex operational problems that pure software developers cannot understand.

WHAT I DELIVER:

Private Equity Operations: Technical due diligence and post-acquisition turnarounds for portfolio companies. I identify risks in the code and leaks in the P&L.

Supply Chain Resilience: Strategy for high-value logistics, global fulfillment (FBA/3PL), and cross-border trade.

AI & Data Strategy: Architecting secure, private AI environments (Python/LLMs) for internal automation and financial modelling.

WHY WORK WITH ME?

I Build What I Advise: I don't just deliver slide decks. I deploy the Python code, set up the warehouse flows, and safeguard the P&L.

Executive Context: As the Chairman of DXLI Holdings, I understand Cap Tables, ROI, and Board governance.

Available for on-site strategic sessions in the GTA and remote leadership globally.
  • English

    Native or bilingual

Can work on-site
Toronto (up to 50km)

Experience

  • CURTAE (Contextual AI Career Intelligence)
    Technical Product Lead
    October 2025 - Today (9 months)
    • • Architected and deployed a vertical AI SaaS platform designed to bypass Applicant Tracking Systems (ATS) through contextual semantic analysis.
    • • Full-Stack Architecture: Built a responsive React frontend and Python/FastAPI backend, integrating vector databases for high-speed semantic matching of candidate profiles.
    • • AI Strategy: Engineered the "Contextual Intelligence" engine using LLM fine-tuning to automate the genera tion of optimized resumes and cover letters, achieving significant improvements in user interview rates.
    • • Commercial Launch: Led the product from concept to commercialization, establishing the pricing model, Stripe payment integration, and go-to-market strategy.
    Artificial Intelligence (AI) Python AI and Advanced Analytics Natural Language Processing (NLP) Generative AI
  • VERIUL (AI Luxury Authentication Infrastructure)
    Principal ProductArchitect (AI & Trust)
    February 2024 - Today (2 years and 5 months)
    • • The Solution: Productized 10+ years of operational expertise into a SaaS utility. Architected "Veriul" from the ground up—a "Digital Chain of Custody" engine using computer vision to detect high-fidelity counterfeits ("su perfakes").
    • • Proprietary AI/ML: Crafted a custom ML model trained on a proprietary dataset of 10,000+ authentic items and forensic data collected over a decade of operations.
    • • Multi-Modal Pipeline: Deployed a Large Vision Model (LVM) reasoning pipeline to analyze stitching density, material grain, and heat stamp irregularities.
    • • Security: Implemented "Zero-Trust" architecture (DMARC/DNS, RBAC) for robust email integrity and human in-the-loop validation queues.
    Computer Vision Deep Learning Fraud Detection Image Recognition SaaS (Software as a Service)
  • DXLI HOLDINGS (Real Estate & Private Capital)
    Executive Chairman | Portfolio Project Lead
    January 2021 - Today (5 years and 6 months)
    Toronto, ON, Canada
    • • Strategic Oversight: Direct board-level strategic planning, governance, and capital allocation for a diversified commercial real estate portfolio.
    • • Financial Engineering: Developed data-driven ROI frameworks and financial models to analyze new invest ment themes and acquisitions, successfully optimizing cash flow visibility.
    • • Negotiation: Represented the organization in high-stakes negotiations with lenders and partners, driving complex contract structuring to secure favorable commercial agreements.
    Mergers & Acquisitions (M&A) Real Estate Development Investment Strategy Asset Management Venture Capital

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Education

  • Bachelor of Arts
    University of Toronto
    2021
    Bachelor of Arts
  • Studies Abroad Program
    University of Oxford
    2019
    Studies Abroad Program

Skill set

Categories