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KEY RESPONSIBILITIES The Vice President, AI & Technology Strategy will serve as the senior executive responsible for architecting and executing a comprehensive AI, digital, and emerging technology strategy across White Owl’s DI portfolio companies. This leader will define a future state vision for how hardware, software, automation systems, deep learning tools, data platforms, industrial IoT, and advanced analytics can transform operations and create long-term competitive advantage.

This role combines strategic thinking, applied innovation, technology leadership, and education to guide both the family office and portfolio companies on how next-generation technologies can reimagine business models, operational workflows, and value‑creation opportunities.

This role will also serve as the chief educator and advisor to C suite leaders across the portfolio—raising executive literacy in AI, emerging technologies, and digital operating models—while collaborating with them to define bespoke technology strategies aligned to each company’s needs.

1. Technology Vision & Strategic Leadership

Develop a multi-year AI and technology vision that integrates advanced software, hardware, and intelligent systems to drive operational excellence and strategic advantage.

Conduct deep, ongoing evaluation of industry‑leading technologies, including:

AI/ML platforms, deep learning architectures, and LLM‑based enterprise tools

Robotics, autonomous equipment, and workflow automation

Telematics, fleet and routing optimization systems

ERP/CRM modernization technologies

Industrial IoT sensors, onboard hardware, and edge computing

Translate technology trends into value creation opportunities,



such as cost reduction, improved routing efficiency, workforce augmentation, predictive maintenance, and enhanced customer experience.

2. Portfolio Company Technology Enablemen

Partner with Presidents, GMs, and C‑suite leaders to develop company‑specific technology strategies, ensuring alignment with financial and operational objectives.

Oversee the deployment of hardware and software solutions that strengthen competitive positioning—for example:

On‑truck sensing systems

AI‑powered safety monitoring and telematics

Automated sorting, waste handling, or plant optimization systems

Advanced mapping, logistics, and dispatching platforms

Guide digital integration during acquisitions, including IT infrastructure assessment, system compatibility, and modernization planning.

Partner with the Director of Strategic Initiatives & Transformation to implement solutions that deliver measurable ROI and reimagine core workflows.

Lead initiatives to modernize and integrate data ecosystems—including data lakes, pipelines, dashboards, and predictive models.

Oversee pilot programs for AI and automation, scaling successful projects across the portfolio with governance, architecture, and adoption support.

4. Executive Education & Thought Leadership





Act as the primary educator for executives on AI maturity, emerging technologies, risks, governance, and industry trends.

Deliver structured learning sessions, workshops, and strategic briefings to elevate digital fluency across the leadership teams.

Help C‑suite leaders understand how hardware/software innovation ties to financial outcomes, operational KPIs, and scalability.

Foster a culture of responsible experimentation, continuous improvement, and cross‑company collaboration.

Mentor technology and digital teams across the portfolio, helping build future leadership bench strength.

Serve as an internal champion for embedding modern hardware/software capabilities into operations, field teams, and decision‑making processes.

QUALIFICATIONS & EXPERIENCE Required

10–15+ years in senior technology leadership, including AI/ML, enterprise architecture, automation, or digital transformation roles.

Proven experience selecting, deploying, and integrating industrial hardware and software systems, including telematics, robotics, sensors, ERP/CRM systems, and advanced analytics platforms.

Demonstrated ability to evaluate and adopt deep learning and industry‑leading technologies to create operational and competitive value.

Success driving transformation across multi‑site, multi‑entity organizations.

Preferred

Background within private equity, family office, or multi‑portfolio environments.

Experience supporting M&A;, integration, or IT modernization within industrial sectors.

Solid executive presence and ability to educate, influence, and collaborate with C‑suite leaders.

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Apply on Kit Job: kitjob.ca/job/2g9gp9

📌 Vice President, AI & Technology Strategy (Markham)
🏢 White Owl Family Office Group
📍 Markham