Fractional CTO & Chief Automation Architect ( Possible Tech Advisory Board)

Leadership Role: Fractional CTO & Chief Automation Architect (Pro Bono / Tech Advisory Board)

Organization: JakeyMac Foundation

Engagement: Volunteer Executive / Advisory Board Member

Time Commitment: 7–10 hours/week during Phase 1 (Pipeline & Engine Architecture), tapering to 2–3 hours/week of strategic stewardship and system optimization.

Location: Remote (St. Pete / Tampa Bay, FL ties welcome)

The Core Problem: Modern Kids Are Tuned Out, and Legacy Education Is Broken

Right now, young minds with massive potential are completely disengaged from traditional learning systems that haven't evolved in decades. Static textbooks, dry lectures, and rigid curricula fail to capture attention in an era built on dynamic feedback loops. Screens are addictive and become ing unsafe.

At the JakeyMac Foundation, we are engineering the alternative: transforming youth education through immersive, gamified audiobooks paired with earbuds and competitive leaderboards for classroom-less learning.

We tap directly into the psychological drivers of modern gaming—streaks, XP, achievement badges, and peer competition—to make foundational knowledge, financial literacy, and life skills addictively engaging for youth.

Here is our operational truth:

Building an innovative, gamified learning vehicle requires a frictionless operational engine. Most non-profits bleed out through administrative sludge—manual data entry, lost donor attributions, disconnected community chats, and clunky donor receipts.

We refuse to operate like a legacy bureaucracy. We run like a high-speed, modern product team—and we need our Technical Guide to architect the AI powered machine behind the mission.

The Call to Adventure: Become the Chief Architect of Our Engine

If you understand strategic leverage, you know the difference between an Opportunity Seeker (who runs around putting out daily fires) and a Strategic Architect (who designs automated systems once so the machine scales without human friction).

We don’t need an IT technician to reset passwords or configure office printers.

We need an elite Fractional CTO & Automation Architect—a systems designer / builder who can help our team connect our gamified youth ecosystem, community hubs, and multi-channel AI Fundraising engine into a unified, self-sustaining operations engine.

The young learners leveling up their lives and the benefactors funding them are the heroes of our/ your journey. You are the master craftsman who builds the vehicle that makes their transformation possible.

The Tech Stack You Command

We don’t run bloated, expensive enterprise software. We deploy agile, programmable, modern rails:

• Automation Brain: n8n (Webhooks, API routers, JSON payload normalization, custom scripts)
• Conversion & CRM Engine: GoHighLevel (GHL pipelines, custom values, automated SMS/Email triggers)
• Omnichannel Giving Rails: Chariot (DAFpay / Donor-Advised Funds), Stripe, Shopify (merch/direct digital checkouts), Pledge.to, Benevity (corporate matching)
• Engagement & Community: Discord (leaderboards, role-gated learner channels, community engagement), WhatsApp Business API (high-touch SMS gamification challenges & donor updates)
• Data Backbone: Google Sheets (real-time, append-only ledgers CPA auditing board reconciliations)

The 2-Phase Architectural Blueprint

• Phase 1: We Built the Machine - You Refine It - (Weeks 1–6 | 7–10 hrs/week)
  • Unified Giving Ingestion: Oversee n8n workflows that listen for incoming donations across Stripe, Shopify, Chariot DAFpay, corporate match platforms (Benevity, Pledge.to).
  • Data Normalization & GHL Integration: Clean, transform, and map fragmented payloads into GoHighLevel with accurate pipeline attribution and custom donor tags.
  • Automated Stewardship Loops: Trigger instant 501(c)(3) tax receipts, founder SMS alerts for major gifts, and automated donor engagement drips.
  • Community & Gamification Rails: Wire webhooks into Discord and WhatsApp to support leaderboards, student achievements, role-based access for volunteers, learners.
• Phase 2: Leverage & Optimization (Ongoing | 2–3 hrs/week)
  • Advisory & Governance: Serve on our Advisory Board, evaluating new educational software integrations, gamification APIs, non-profit tech grants, and security pr otocols.
  • System Reliability: Monitor webhook health, audit API rate limits, and maintain data backup integrity.

The Profile of Our Ideal Architect

• Mastery of Workflow Engines: Fluent in n8n (or Make), deeply comfortable with webhooks, REST APIs, and writing clean JavaScript/Python transformation nodes when native modules aren't enough.
• GoHighLevel Specialist: You understand GHL inside and out—custom fields, sub-account logic, webhook triggers, and multi-channel conversational automation.
• Fintech & Non-Profit Rails Fluent: You know how Stripe, DAFs (Chariot), and workplace matching engines (Benevity) process transactions under the hood.
• Passionate About Gamified Learning: You recognize that gamification, audio narrative, and competitive leaderboards are the future of youth education.

What You Walk Away With

• Executive Advisory Board Credential: Formal appointment as Fractional CTO / Technology Director on our official board roster—an executive credential for your resume or advisory portfolio.
• A Signature Architecture Asset: A fully functional, production-grade non-profit automation machine you can reference as definitive proof of your systems architecture mastery.
• Direct Generational Impact: You won't be writing throwaway code to optimize banner clicks. Your infrastructure directly supports a gamified platform that makes education exciting, rewarding, and accessible to youth who need it most. And supporting the AI Fundraising engine.
• Executive Network Access: Direct collaboration with foundation leadership, community innovators, and our philanthropic partners.

How to Step Up

We know A-players value leverage and respect their own time. Skip the formal cover letter.

Send an email with your CV, LinkedIn or GitHub profile and quick answers to these two questions:

1. What is the most elegant n8n or API webhook pipeline you’ve built to date?
2. Why does building the operational engine for a gamified youth education non-profit appeal to you right now?