Senior Executive, Technology Strategy and Transformation

Senior Executive, Technology Strategy and Transformation

Location: Hybrid, Corporate HQ in downtown Toronto

Employment Type: Full-Time

Compensation: Base + Commission

The Role

We are seeking an experienced Senior Technology Executive to provide strategic direction, executive advisory, and technical leadership across client engagements and within QuantumSmart.

This role requires a combination of business acumen, enterprise technology expertise, and executive presence. You will assess complex technology environments, identify gaps and opportunities, develop strategic roadmaps, and guide organizations through technology transformation.

You will work directly with CEOs, CIOs, CISOs, boards, and senior stakeholders, translating business priorities into clear technology strategies and actionable solutions. You will also provide technical leadership to project teams, contribute to business development, and play an active role in strengthening QuantumSmart's client relationships and growth.

Work closely with Project Managers and technical teams to ensure the effective execution and delivery of technology initiatives, providing technical guidance, strategic direction, and support in managing client expectations, priorities, risks, dependencies, and escalations.

We encourage candidates to apply even if they do not meet every qualification.

Who is QuantumSmart

Holistic Insight. The Future in Focus.

QuantumSmart is a technology advisory firm helping organizations turn complexity into clarity and action. We provide holistic insight across business, technology, risk, data, processes, and people, helping leaders make informed decisions and build for what comes next.

Key Responsibilities

1. Technology Strategy & Executive Advisory

• Assess organizations' technology landscapes, identifying gaps, risks, dependencies, opportunities, and areas for improvement.
• Develop comprehensive technology strategies and roadmaps that align business objectives with technology capabilities and investment priorities.
• Advise CEOs, CIOs, CISOs, boards, and senior stakeholders on technology strategy, infrastructure, cybersecurity, risk, and emerging technologies.
• Translate complex business requirements into clear strategic direction and actionable recommendations.
• Provide executive-level insight into technology investments, modernization, operational efficiency, and long-term business resilience.
• Navigate complex and evolving business environments, bringing structure to ambiguity, prioritizing competing demands, and maintaining focus on strategic outcomes.

2. Technology Transformation, Technical Oversight & Knowledge Transfer

• Provide strategic technical oversight across enterprise technology environments, including infrastructure, cloud, applications, cybersecurity, and data.
• Develop and lead architecture direction, review, and maintain technical documentation and key project artifacts, including technology assessment reports, architecture diagrams, technical recommendations, solution designs, and implementation roadmaps, ensuring clarity, accuracy, and alignment with client requirements.
• Address business requirements, scalability, security, and industry best practices.
• Guide technology transformation and modernization initiatives, ensuring alignment between current and target states, business objectives, and expected outcomes.
• Provide strategic oversight across technology initiatives, ensuring effective coordination between technical teams, project delivery, resources, dependencies, and client priorities.
• Deliver client education, training sessions, and knowledge-sharing engagements to strengthen technology understanding, build internal capabilities, and enable informed decision-making.
• Guide technology teams and client stakeholders in regulated environments, with consideration for standards such as SOC 2 Type II and ISO 27001.

3. Client Engagement & Business Development

• Lead technical discovery and executive discussions, identifying client challenges, business priorities, and opportunities where QuantumSmart's expertise can create value.
• Develop and present strategic recommendations, technology roadmaps, and solutions that address client needs and align with their business objectives.
• Act as a senior advocate for client interests, ensuring business priorities are understood, expectations are aligned, and recommendations deliver meaningful value.
• Build trusted relationships with senior executives and key stakeholders, establishing credibility through strategic insight, technical expertise, and a strong understanding of business.
• Identify opportunities to expand existing client engagements and contribute to new business development.
• Contribute to proposals, statements of work, presentations, and other business development activities, translating complex technical capabilities into clear business value.
• Work closely with QuantumSmart's leadership team to shape opportunities, strengthen client relationships, and drive sustainable business growth.

4. Leadership, Mentorship & Thought Leadership

• Mentor and guide team members, sharing knowledge and elevating technical and professional capabilities across the organization.
• Collaborate with internal teams and executive leadership to promote continuous learning, innovation, and high standards of delivery.
• Present complex technical concepts in clear, business-focused language to both technical and non-technical audiences.
• Contribute to industry thought leadership through professional networking, LinkedIn engagement, and sharing relevant technology perspectives.
• Demonstrate leadership through accountability, transparency, initiative, and a commitment to QuantumSmart's values.

Qualifications

• Minimum 5+ years in a senior IT leadership role, such as IT Manager or above, with demonstrated responsibility for technology strategy, operations, or transformation.
• Proven experience in IT operations, technology strategy, enterprise technology environments, and working alongside architecture and technical teams to evaluate and guide technology solutions.
• Strong knowledge of enterprise cloud platforms and productivity ecosystems, including AWS, Microsoft Azure, Google Cloud Platform (GCP), Microsoft 365, and Google Workspace.
• Understanding of cybersecurity principles, enterprise security architecture, and recognized security frameworks.
• Ability to assess complex technology environments and translate technical challenges into business value and strategic recommendations.
• Strong executive presence, with the confidence and credibility to engage CEOs, CIOs, CISOs, boards, and senior stakeholders.
• Exceptional presentation, communication, and stakeholder engagement skills.
• Strong written and verbal communication skills in English.

Preferred Experience

• Experience working across enterprise technology and security environments.
• Understanding of regulatory and compliance frameworks, including GDPR, PCI, and other industry standards.
• Experience working in highly regulated industries.
• Experience with CMMI or other IT maturity and assessment frameworks.
• Awareness of emerging technologies, including AI and quantum computing, and the ability to assess their potential business implications.
• Experience contributing to business development, client acquisition, or account growth.

What We Offer

• Annual salary with performance-based incentives (Commission + Bonus).
• Health benefits.
• Opportunities for career growth, certifications, and leadership development.
• Exposure to diverse technology environments, industries, and complex business challenges.
• Opportunities to work directly with executives and contribute to meaningful organizational transformation.
• A collaborative environment that values innovation, knowledge sharing, accountability, and continuous learning.
• Hybrid work model, with occasional travel for client engagements and in-office collaboration at our downtown Toronto headquarters.

Join Our Team

At QuantumSmart, we value leadership, integrity, strategic thinking, transparency, and a growth mindset. We believe in building strong teams, fostering meaningful client relationships, and delivering measurable business value. We are looking for an experienced professional who is motivated to make an impact, contribute to meaningful outcomes, and grow alongside an ambitious organization.

Apply on LinkedIn.