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Jackson Macdonald

About

I like the part between “this process is broken” and “this is how we work now.”

My career has been a progression toward one kind of work: taking ambiguous operational problems and turning them into systems people can actually use.

I started as a teacher, moved into e-commerce and enterprise technology implementation, led software transformation across a distributed franchise network, and eventually became deeply involved in enterprise AI adoption and workflow automation.

Today, I work across business strategy, implementation, AI, automation, and change. I’m comfortable sitting with an operator to understand why a process is frustrating, translating that conversation into requirements, building or prototyping a better workflow, working with technical teams when necessary, and then helping the organization adopt the change.

That last part matters to me.

A technically impressive solution that never becomes part of someone’s real workflow is not a successful implementation.

I’m particularly interested in roles where I can own the space between customer or stakeholder discovery and measurable deployed outcomes — especially in AI implementation, AI deployment, forward-deployed product, AI transformation, and product-adjacent solutions work.

Start with the problem, not the technology.
The best automation removes work, not just clicks.
Human-in-the-loop is a design choice, not a failure of automation.
Deployment is not done when the system goes live. It is done when the new behavior becomes normal.
If we cannot explain the business outcome, the AI project probably is not ready.

Career timeline

  1. Jan 2024 – Present

    Global AI Initiative — Project Manager & AI Subject Matter Expert

    AlphaGraphics & PostNet World Headquarters / Fortidia

    • Led enterprise AI transformation supporting 3,500+ employees across 10 global brands
    • Partnered with leadership to identify use cases and implementation priorities
    • Built AI-enabled workflow automations
    • Led enablement and adoption
    • Reported adoption, impact, and roadmap recommendations to executives
  2. Aug 2024 – Present

    Business Development Consultant

    AlphaGraphics & PostNet World Headquarters / Fortidia

    • Strategic advisor to 20 franchise businesses
    • Discovery around operational challenges, technology, CRM, and growth
    • Data-driven business recommendations
    • Workshops and capability building
    • Portfolio associated with 8% YoY regional growth
  3. Aug 2025 – Nov 2025

    Post-Acquisition Integration Manager — Sydney, Australia

    AlphaGraphics & PostNet World Headquarters / Fortidia

    • Selected by executive leadership for onsite international integration
    • 100-location acquired organization
    • Transformation roadmap
    • Governance
    • Cross-functional workstreams
    • Executive reporting
    • Adoption frameworks
  4. Oct 2023 – Aug 2024

    IT Project & Implementation Manager

    AlphaGraphics & PostNet World Headquarters / Fortidia

    • Enterprise software transformation across 225+ locations
    • Requirements
    • Vendor and technical partnership
    • Training and adoption
    • Implementation frameworks
    • Reporting and risk management
  5. Dec 2022 – Oct 2023

    E-Commerce Project Manager

    AlphaGraphics & PostNet World Headquarters / Fortidia

    • E-commerce implementation
    • Technical/business alignment
    • Certification and reporting automation across 250+ locations
    • Training programs
    • Cross-functional delivery

Earlier career

8th Grade Math Teacher

Before working in technology and transformation, I taught 8th grade math. That experience still shapes how I work: explain complex ideas clearly, meet people where they are, and recognize that adoption depends on understanding — not just instruction.

Building AI systems that have to work in the real world?

I’m interested in AI implementation, deployment, transformation, forward-deployed, and product-adjacent roles where I can own the path from business problem to deployed outcome.