Director Technology, AI & Digital Products

Socket.dev; Toronto; Hybrid; CAD 150,000 - 230,000; Full time

Job summary

Socket.dev, a fast-growing AI advisory firm, seeks a Director of Technology & Digital Transformation to lead client-facing technology advisory. Hybrid role in Ontario, with regular travel to client sites, working with executives and engineers.

You will assess client operations, turn findings into practical roadmaps for modernization and AI adoption, lead engagements from discovery to delivery, and mentor teams while shaping advisory methodologies.

Qualifications

• Extensive senior technology leadership experience, preferably at CIO/CTO level.
• Track record of delivering end-to-end digital transformation and AI initiatives.
• Ability to translate business needs into technology strategy and roadmaps.
• Strong communication with executives and technical teams; client relationship management.

Responsibilities

• Lead technology and operational assessments for clients, engaging both business and technical stakeholders.
• Translate business challenges into clear, actionable technology and AI strategies.
• Provide senior technical leadership and governance across client engagements.
• Present findings and recommendations to executive and technical audiences alike.
• Support new business development through discovery, solutioning, and proposals.
• Mentor technical teams and help build out our advisory methodologies.

Job description

Director, Technology, AI & Digital Products

Location: Hybrid (Ontario - with regular travel to client sites)

About the role

We're a fast-growing technology and AI advisory firm serving enterprise clients, and we're looking for a Director of Technology & Digital Transformation to lead our client-facing technology advisory practice. This is a senior, hybrid role equally at home in the boardroom with executives and in a technical conversation with engineers and architects.

You'll walk into client organizations, assess how the business runs and how technology supports (or holds back) it, and turn that understanding into practical strategies and roadmaps for modernization, AI adoption, and digital transformation. You'll lead engagements from initial discovery through delivery oversight, working closely with our architects, engineers, and delivery teams to make sure recommendations actually get built and get results.

What you'll do

• Lead technology and operational assessments for clients, engaging both business and technical stakeholders
• Translate business challenges into clear, actionable technology and AI strategies
• Provide senior technical leadership and governance across client engagements
• Present findings and recommendations to executive and technical audiences alike
• Support new business development through discovery, solutioning, and proposals
• Mentor technical teams and help build out our advisory methodologies

What we're looking for

We're looking for someone with substantial, progressive experience in technology leadership - ideally having operated at or near the CIO/CTO level, with a track record of leading digital transformation initiatives end to end. You should be someone who thinks in terms of business outcomes as much as technical architecture, communicates with equal credibility across executive and engineering audiences, and is comfortable managing multiple client relationships at once in a consulting or professional-services environment.

Work Location: Hybrid in Ontario