Job Description: 

Technology Strategy

• Develop and execute Company's long-term technology roadmap aligned with business strategy.
• Lead modernization of the platform, including cloud architecture, scalability, performance, and security.
• Evaluate emerging technologies and recommend investments that improve competitive advantage.
• Establish technology standards, governance, and engineering best practices.

Engineering Leadership

• Lead and mentor Software Development, QA, DevOps, Infrastructure, and Architecture teams.
• Build a high-performing engineering culture focused on accountability, collaboration, continuous improvement, and innovation.
• Recruit, develop, and retain top technical talent.
• Establish KPIs to improve engineering effectiveness, quality, and delivery.

Product Innovation

• Partner with Product Management to define technical direction for future products.
• Drive delivery of scalable SaaS solutions.
• Champion customer-focused innovation.
• Balance technical debt reduction with new product development.

Artificial Intelligence & Automation

• Develop the organization's AI strategy.
• Identify opportunities to embed AI capabilities throughout the Company platform.
• Evaluate and govern the use of technologies such as:
  • Azure OpenAI
  • Microsoft Copilot
  • Retrieval-Augmented Generation (RAG)
  • Intelligent automation
  • Predictive analytics
• Ensure AI solutions are secure, scalable, and aligned with customer needs.

Infrastructure, Security & Operations

• Ensure platform reliability, uptime, disaster recovery, and business continuity.
• Oversee cloud infrastructure and DevOps practices.
• Maintain cybersecurity standards and compliance.
• Implement monitoring, observability, and incident response processes.

Cross-Functional Leadership

• Partner with:
  • Product Management
  • Professional Services
  • Customer Success
  • Sales
  • Executive Leadership

to ensure technology investments align with strategic priorities.

• Participate in customer meetings, executive presentations, and strategic planning.

Operational Excellence

• Improve software delivery speed while maintaining quality.
• Reduce technical debt through disciplined modernization.
• Establish engineering metrics including:
  • Deployment Frequency
  • Lead Time
  • Change Failure Rate
  • Platform Availability
  • Mean Time to Resolution (MTTR)
  • Customer Defect Rates

Qualifications

Required

• Bachelor's degree in Computer Science, Engineering, or related field.
• 5+ years of progressive software engineering experience.
• 3+ years leading engineering organizations.
• Proven experience delivering enterprise SaaS platforms.
• Experience leading cloud migration and modernization initiatives.
• Strong understanding of:
  • Microsoft Azure
  • Cloud architecture
  • APIs
  • Microservices
  • CI/CD
  • DevOps
  • Security
  • Scalable system design
• Experience managing engineering budgets and technology roadmaps.
• Strong executive communication and leadership skills.

Preferred

• Experience within ERP, logistics, transportation, moving & storage, or field service software.
• Experience integrating AI and machine learning into commercial software products.
• Familiarity with Microsoft Copilot, Azure OpenAI, and modern AI development frameworks.
• Experience working within a private equity or software portfolio environment.
• MBA or Master's degree is considered an asset.

Leadership Competencies

The successful candidate will demonstrate:

• Strategic thinking and business acumen
• Technical depth with executive-level leadership
• Customer-first decision making
• Strong organizational and change leadership
• Excellent coaching and mentoring abilities
• Data-driven decision making
• Ownership and accountability
• Continuous improvement mindset

Success Measures (First 12 Months)

The successful CTO will:

• Establish a multi-year technology roadmap aligned with company strategy.
• Improve engineering predictability and delivery velocity.
• Reduce technical debt while accelerating innovation.
• Advance cloud modernization initiatives.
• Launch meaningful AI-enabled product capabilities.
• Improve software quality, platform reliability, and security.
• Strengthen engineering culture through leadership development and talent retention.
• Build stronger alignment between Product, Engineering, Customer Success, and Professional Services.

Business Unit: 

Scheduled Weekly Hours:

Number of Openings Available: 

Worker Type: 

More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.