Chief Technology Officer

Jonas Software

$180K — $220K *
US-AnywhereRemote in Canada
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 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 and cloud architecture.
  • Experience managing engineering budgets and technology roadmaps.

Responsibilities

  • Develop and execute long-term technology roadmap aligned with business strategy.
  • Lead platform modernization focusing on cloud architecture and security.
  • Evaluate emerging technologies for competitive advantage.
  • Build a high-performing engineering culture fostering collaboration and innovation.
  • Drive the delivery of scalable SaaS solutions in partnership with Product Management.
  • Oversee cloud infrastructure and maintain cybersecurity compliance.
  • Establish effective KPIs for software engineering quality and delivery.

Benefits

  • Opportunities for professional growth and development.
  • Supportive work environment focused on innovation and improvement.
  • Emphasis on work-life balance through achievable project goals.
Full Job Description
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:
Efficient Workflow Solutions
Scheduled Weekly Hours:
40
Number of Openings Available:
1
Worker Type:
Professional (Fixed Term)

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