Lead AI & Systems Developer (Python) (Collingwood)

Lead AI & Systems Developer (Python) Our client is a 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 Contract generation 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 current 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. Cross-Portfolio Collaboration 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, Type Script, 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! Apply on Kit Job: kitjob.ca/job/2om5bd