Head of AI

Position: Head of AI
Location: Canada, Toronto
Reports to: CEO
Employment Type: Full-Time

About Solen Software Group: Solen Software Group is an investment and operating company that acquires and operates proven software businesses that have significant growth potential in a variety of vertical markets, enabling them to be market leaders in their niche industry. Solen owns several software companies in various market spaces: Human Resource Technology, Fleet Telematics, Asset Management,  E-Health, Document Management, and other innovative software solutions in a variety of industries. Solen is backed by a group of advisors and investors that have built software businesses of material scale (10-100M in ARR) and advised many.

About the role: The Chief Information & Technology Officer (CITO) provides strategic leadership at the intersection of technology, governance, and business transformation. This role ensures that technology across the organization’s diverse portfolio of companies is aligned with corporate strategy, operates under consistent standards, and drives value creation. The CITO oversees IT governance, sets enterprise-wide technology policies, conducts technology due diligence for acquisitions, and ensures best practices are implemented to maximize scalability, security, and efficiency. The role also champions AI adoption—both programmatically and operationally—to accelerate innovation and improve business outcomes.

The successful candidate will work from our office in Canada. 
Key responsibilities:

Strategic Leadership & Governance

• Define and enforce enterprise-wide IT and technology governance frameworks.
• Establish standards, policies, and best practices across infrastructure, software development, cloud adoption, cybersecurity, and AI.
• Partner with executive leadership to align technology strategy with overall business objectives.
• Ensure compliance with relevant regulatory, security, and data privacy requirements.

Technology & AI Adoption

• Drive standardization of tools, platforms, and methodologies across portfolio companies.
• Lead AI adoption initiatives, embedding intelligent automation, machine learning, and analytics into products, services, and operations.
• Evaluate and optimize enterprise architecture, including cloud infrastructure, data management, and AI integration.
• Oversee the adoption of modern development practices, DevOps, system monitoring, and AI-driven development productivity tools.
• Champion innovation while ensuring cost-effectiveness and operational resilience.

Due Diligence & M&A; Support

• Lead technology due diligence during acquisitions, assessing scalability, risks, AI readiness, and integration potential.
• Provide executive-level reports summarizing technology risks, strengths, and recommendations.
• Develop post-acquisition integration playbooks and technology roadmaps to unify systems and processes, including AI enablement strategies.

Risk, Security & Compliance

• Implement frameworks for cybersecurity, business continuity, and disaster recovery.
• Establish AI governance to ensure ethical, secure, and compliant use of AI technologies.
• Proactively identify technology risks and establish mitigation strategies.
• Ensure IT operations across the group meet reliability and performance standards.

Stakeholder Engagement & Leadership

• Collaborate with portfolio company leaders to guide technology modernization, AI adoption, and best-practice implementation.
• Build and mentor a distributed network of technology and AI leaders across acquired businesses.
• Act as a trusted advisor to the board and executive team on technology and AI trends that drive competitive advantage.

Key Requirements

• Proven track record in senior IT/technology leadership roles (CTO, CIO, or equivalent).
• Experience in M&A; technology due diligence and post-merger integration.
• Strong knowledge of governance, compliance, and IT frameworks (e.g., ITIL, COBIT, ISO 27001).
• Expertise in enterprise cloud, AI/ML, automation, modern software development, and security practices.
• Excellent stakeholder management, communication, and strategic planning skills.
• Must be legally authorized to work in Canada.
  We thank all applicants for their interest; however, only those selected for an interview will be contacted.

Equal Opportunity and Advancement Statement 

Solen Software Group is a performance-oriented organisation that values career advancement, internal development, and transparent practices. We are an equal opportunity employer and are committed to creating an inclusive, welcoming environment for all team members. 

We do not discriminate on the basis of race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other legally protected status. All qualified applicants will receive consideration for employment without regard to any of these characteristics. 

Recruitment Disclaimer 

Solen Software Group will never request payment, banking information, or other sensitive personal or financial details during any stage of the recruitment process. All official communication will come from a verified @solensoftware.com email address. Any outreach outside these standards should be disregarded and reported through our official channels. 

Thank You 

We thank all applicants for their interest in joining Solen Software Group. Only candidates selected for an interview will be contacted. 

Solen-isms: 

Pioneering 

Pioneering driven by opportunity, using first principles thinking and unbound by tradition or rules. 

Mutual Elevation 

Committed to growth, elevating teams, developing future leaders, and removing barriers to mastery and joy. 

Learn-It-Alls 

Learn-it-alls, not know-it-alls, embracing failure as part of growth and progress. 

Figure-It-Out-iveness 

Embracing challenges, fostering growth, and taking initiative, leaders thrive on hard work and high failure tolerance. 

Completionists 

We exhibit stick-to-it-iveness. We are Completionists. We adapt. We think long-term. No plan B. We are all in. We burn the boats. 

Ownership Mindset 

We own the mission. We don't wait to be told. We lead, fix, and build as if it were ours. When problems arise, we run toward them, not away. 

Dialectical 

We learn through conversation. We ask, listen, question, and evolve — valuing disagreement as a tool for alignment and deeper understanding. 

Benchmark to Best 

We seek out excellence. We measure ourselves against the best and adapt quickly, always looking for the edge that moves us forward. 

Will to win 

Leaders relentlessly pursue potential, reject mediocrity, and get what they tolerate. 

Candor 

We communicate with integrity, transparency, and respect in all conversations. 
 
Band of beavers 

We are relentlessly resourceful, industrious semi-aquatic rodents. Our teeth are self-sharpening. As multi-faceted generalists, we terraform 

Frugality 

Achieving more with less, focusing on quality, long-term value, and company-wide responsibility.