Lead AI & Systems Developer (Python)

Lead AI & Systems Developer (Python) Permanent | Collingwood, ON | November 20, 2025

Our client is a founder‑led group of companies operating across aviation, telecom, hospitality, craft brewing, commercial real estate, luxury charters, and fintech.

They are building an internal AI platform powering operational efficiency across their entire portfolio, including:

AI assistants

Workflow automation

HR onboarding

Data integration

We are looking for a hands‑on Python developer who is excited to build, ship, and scale new tools as their digital ecosystem expands.

Job Overview

This is a hybrid role combining software development, systems integration, and applied AI. You will build the next phase of our internal software, connect systems across different businesses, and introduce AI/automation where it creates clear operational value.

Responsibilities

Build & Expand existing AI + Systems Platform

Develop new modules in Python (FastAPI), including:

HR onboarding + employee data vault

Contract generation + digital signing workflows

Document upload + KYC/ID verification components

Knowledge base ingestion + vector database search

Maintain and improve existing React frontend + Azure backend.

Integrations & Automation

Build lightweight API integrations between POS, HR, booking, payroll, and financial systems.

Create automations and scripts that reduce time and manual work (Power Automate, Zapier, custom Python scripts).

Develop dashboards and reporting tools using AI, Power BI, or custom code.

Infrastructure & Security

Manage cloud environments (Azure, Google Workspace).

Improve access control, data protection, and backup policies.

Maintain logging, monitoring, and error‑tracking processes.

Work directly with managers across:

Telecom field operations

Aviation & airport operations

Hospitality & brewery

Yacht and aircraft charter

Real estate & family office

Translate operational problems into simple, functional technology solutions.

Targeted Candidate Profile/Required Experience

Experience

2–6 years of experience in software development, automation, or tech operations.

Strong Python skills, especially FastAPI, scripting, integrations, or backend development.

Experience with cloud platforms (Azure, GCP, or AWS).

Bonus: React, TypeScript, or full‑stack familiarity.

Mindset

Builder mentality: loves shipping features quickly and improving iteratively.

Comfortable working directly with a founder and operators.

Highly adaptable, enjoys working across multiple industries.

Curious, resourceful, and self‑directed.

You Are Probably Someone Who…

Has built side projects, SaaS tools, or automations independently.

Loves solving operational problems with technology.

Thrives in variety and hates monotonous corporate environments.

Why This Role Is Rare

This is not a siloed corporate tech job.

This is a chance to:

Build a live internal product used across multiple industries

Apply AI in real, tangible workflows

Potential to grow into a leadership role as the digital organization matures

Work directly with ownership on high‑impact projects

You will see your work make a difference immediately.

If you are interested and have the above experience please forward a MS Word copy of your resume. Thanks!

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