Job Description:

Senior Director of AI

Jonas Club

THE COMPANY

Gary Jonas Computing Ltd was established in September 1990 with a mandate to be a client-oriented and technology-driven software application company with industry-related professionals. Jonas Software is the leading provider of enterprise management software solutions to the Private and Semi-private Club, Foodservices, Construction, Metal Service Centers, Moving & Storage and Attractions & Leisure, Fitness & Sports industries. Within these independent vertical markets, Jonas boasts 12 distinct brands, all of which are respected and longstanding leaders within their own domain. Jonas’ vision is to be the branded global leader across the aforementioned seven vertical markets and to be recognized by customers and respective industry stakeholders as the trusted provider of Software for Life and as an ambassador for technology, product innovation, quality, and customer service. Jonas Software is the valued technology partner of over 8000 customers worldwide in 15 countries.

POSITION

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.

JOB 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.

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More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.