AI and Digital Transformation Lead

Toronto, Canada | Full-time

JOB DESCRIPTION

Reporting to the Chief Technology Officer (CTO), the AI and Digital Transformation Lead is a strategic technology leader responsible for advancing the company’s AI strategy and automation initiatives. This role combines artificial intelligence, CRM technologies (Microsoft Dynamics 365), and web platforms (WordPress) to design and deliver intelligent, scalable solutions that enhance user experience, improve operational efficiency, streamline processes, and support data-informed decision-making.

The AI and Digital Transformation Lead manages the design, implementation, integration, and governance of AI-powered solutions across the company’s technology ecosystem. Working collaboratively across departments, the incumbent drives innovation and ensures the seamless integration and reliable flow of data, workflows, and AI-driven insights between the company’s public-facing WordPress platforms and internal CRM and Microsoft environments. The role is accountable for delivering AI features that are actively used in production, reducing or eliminating manual processes through automation, and enabling smarter member engagement, enhanced user experiences, and greater organizational effectiveness across the organization.

KEY RESPONSIBILITIES

Engagement and operational efficiency, with a focus on:

• Microsoft Dynamics 365 CRM

  • Lead the optimization, administration, and continuous enhancement of Microsoft Dynamics 365 to improve member engagement, service delivery, data quality, reporting capabilities, and organizational efficiency.

• WordPress Website and Digital Platform Integration

  • Oversee the integration of WordPress websites with internal business systems and digital platforms to create a seamless user experience, improve data sharing, and support online service delivery.

• Microsoft 365 (Outlook, Word, Excel, Teams, SharePoint)

  • Maximize the value of the Microsoft 365 ecosystem by promoting collaboration, document management, communication, knowledge sharing, and productivity across the organization.

• Email and Workflow Automation

  • Design and implement automated workflows and business processes that reduce manual effort, improve operational efficiency, enhance accuracy, and accelerate service delivery.

• Secure AI Adoption

  • Establish a secure and governed approach to Artificial Intelligence by identifying practical use cases, implementing appropriate controls, ensuring compliance with organizational policies, and enabling staff to use AI responsibly and effectively.

AI strategy and enablement

• Collaborate with the CTO and create a prioritized multi-year AI roadmap aligned with organizational objectives and risk mitigation priorities

  • Identify AI use cases that span across CRM, WordPress, and Microsoft 365, enabling end-to-end automation and insight.

  • Define patterns for AI-assisted engagement journeys (web → CRM → email → reporting).

Business development and digital strategy collaboration

• Partner with the Director of Business Development to identify and implement technology solutions that support organizational growth, member engagement, digital services, and operational efficiency.

• Partner with the Director of Marketing and Communications to develop digital initiatives that improve user acquisition, retention, communications, and service delivery.

• Provide technical insight into emerging AI, CRM, and web technologies that can support strategic business objectives.

• Assist in evaluating and integrating new digital platforms, tools, and automation opportunities.

AI and automation development

• Design, build, and deploy AI driven solutions (e.g., chatbots, recommendation engines, predictive models).

• Integrate AI capabilities into business workflows using tools like Azure AI, Power Platform, and APIs.

• Identify opportunities to automate manual processes across CRM and web platforms.

• Ensure all CRM and WordPress integrations comply with data privacy, security, and organizational standards.

• Define guardrails for AI use across internal and public systems.

• Document integrations, workflows, and AI decision logic.

Microsoft Dynamics 365

• Customize and extend Dynamics 365 (CRM) using plugins, workflows, and Power Platform (Power Automate, Power Apps).

• Integrate AI models and automation into Dynamics (e.g., lead scoring, member engagement insights).

• Work with stakeholders to translate business requirements into AI-driven solutions.

• Integrate CRM data into WordPress, Outlook, Word, Excel, and Teams using AI and automation to:

  • Improve communications

  • Generate summaries and insights

WordPress Development and Integration

• Integrate WordPress websites with Microsoft Dynamics 365 CRM to:

  • Capture and sync form submissions, registrations, inquiries, and user activity

  • Automate lead/member creation and updates

  • Improve segmentation and personalization

  • Design scalable integration approaches using APIs, connectors, or middleware.

• Partner with web teams and vendors to ensure integrations are secure, performant, and well-maintained.

• Leverage AI to enhance WordPress-driven experiences (e.g., intelligent forms, content personalization, analytics insights).

Data and Integration

• Design integrations between systems (Dynamics, WordPress, third-party platforms)

• Work with APIs, webhooks, and middleware to ensure seamless data flow

• Analyze data to support AI model training and optimization

Security and Governance

• Ensure solutions follow best practices for data privacy, security, and compliance

• Implement role-based access and secure data handling across platforms

EXPERIENCE, QUALIFICATIONS AND EDUCATIONAL REQUIREMENTS

• 5+ years’ experience in one or more of:

  • AI/ML solution development

  • Business automation

  • Microsoft enterprise platforms

• Solid experience with WordPress (theme/plugin development, REST APIs)

• Hands‑on experience with Microsoft 365, Power Platform, and automation tools

• Experience with AI/ML frameworks (Azure AI, OpenAI APIs, Python, etc.)

• Solid understanding of AI‑driven workflows and integration design

  Proficiency in:

  • Power Platform (Power Automate, Power Apps)

  • RESTful APIs and integrations

• Experience integrating systems via APIs, connectors, or low‑code platforms

• Strong communication skills with both technical and non‑technical stakeholders

ASSETS

• Experience with Azure services (Azure Functions, Logic Apps, Application Insights)

• Familiarity with Power Pages / Dynamics Portals

• Experience in CRM driven organizations

• Knowledge of DevOps practices (CI/CD pipelines, version control)

• Experience with Dynamics‑WordPress connectors or custom integrations

• Familiarity with CMS security and data governance considerations

• Experience using AI to enhance digital engagement platforms

• Azure, Power Platform, or Dynamics certifications

• Experience with Shopify, including integrations, customizations, or API connectivity, is considered a strong asset

PHYSICAL REQUIREMENTS AND WORK ENVIRONMENT

• Work will be performed at the company’s Canada’s Office and from home (hybrid work schedule) with occasional travel to seminars and/or training. Occasional evening and weekend work for problem resolution, or deadlines as required.

• Regularly sits at a desk and operates electronic equipment

• Manual dexterity required to use desktop computer, telecommunications equipment and peripherals

• From time to time, some lifting, up to 20 lbs. may be required to retrieve equipment

WORK ENVIRONMENT
The work environment described is a representation of those an employee encounters while performing the essential functions of this role. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

BENEFITS

Compensation: $140K–$150K base salary, plus a strong benefits and pension package.

Work arrangement: Hybrid, with a minimum of two days per week in the Toronto office.