Senior Director of AI

Job Description

Senior Director of AI

Gary Jonas Computing Ltd was established in September 1990 as a client‑oriented, technology‑driven software application company. Jonas Software leads the enterprise management software market for Private and Semi‑private Clubs, Foodservices, Construction, Metal Service Centers, Moving & Storage, Attractions & Leisure, Fitness & Sports, and other industries. With 12 distinct brands, Jonas serves over 8,000 customers across 15 countries and operates in more than 30 markets worldwide.

We are seeking a dynamic, strategic leader to oversee AI initiatives, driving transformative projects that enhance product capabilities, improve operational efficiencies, and unlock new revenue opportunities. As a member of the Senior Leadership Team, this role will shape the strategic direction of AI deployment within the organization.

Job Responsibilities

• Develop and own the company’s AI strategy, ensuring alignment with long‑term business goals and market opportunities.


• Work with Product and R&D teams on the design and development of AI projects.


• Drive end‑to‑end AI solution development, from research and prototyping to scalable production deployment.


• Evaluate emerging AI technologies and industry trends, recommending adoption strategies to maintain competitive advantage.


• Establish AI governance standards, including model ethics, safety, privacy, data integrity, and responsible AI practices.


• Collaborate with executive leadership to identify high‑impact AI use cases across products, operations, and customer experiences.


• Set KPIs and performance metrics for AI initiatives and ensure measurable ROI and business value delivery.


• Communicate AI vision and outcomes to internal stakeholders and external audiences, including customers, partners, and industry forums.

Qualifications

• Demonstrated ability to translate business problems into AI solutions with measurable impact on revenue, efficiency, or customer experience.


• Proven track record of delivering AI projects in production, including scalable architectures, model deployment, monitoring, and lifecycle management.


• Experience identifying and implementing AI solutions that delivered tangible business value (e.g., revenue growth, cost reduction, efficiency improvement).


• Expert‑level understanding of modern AI techniques such as deep learning, LLMs, generative AI, reinforcement learning, NLP, and applied machine learning.


• Strong leadership experience leading high‑performance technical teams and influencing executive stakeholders.


• Experience with AI governance, including model explainability, risk assessment, fairness, privacy, and regulatory compliance.


• Excellent communication skills, with the ability to present complex AI concepts to technical and non‑technical audiences.


• Experience building and managing budgets, vendor relationships, and cross‑functional programs at an enterprise scale.

Business Unit: Jonas Club

Scheduled Weekly Hours: 37.5

Number of Openings Available: 1

Worker Type: Regular

Pay Scale: $130,000–$150,000 CAD annually