At a Glance
- Tasks: Lead tech strategy, modernize platforms, and drive AI innovation.
- Company: Join a forward-thinking company focused on efficient workflow solutions.
- Benefits: Competitive salary, remote work, and opportunities for professional growth.
- Other info: Dynamic environment with a focus on collaboration and continuous improvement.
- Why this job: Shape the future of technology while making a real impact.
- Qualifications: 5+ years in software engineering and 3+ years in leadership roles.
The predicted salary is between 123750 - 151250 $ per year.
Compensation & Role Details:
- Expected Salary Range: The expected base salary range for this role is between $160,000– $175,000 CAD/USD, depending on experience and qualifications.
- Role Type: New Role
- AI Disclosure: AI may be used during the hiring process.
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, and 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, and 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.
Chief Technology Officer in Winnipeg employer: EWS Group
CORA Group, as part of Jonas Software, is an exceptional employer that prioritizes employee culture and growth while driving innovation in the M&A sector. With a commitment to professional development and a collaborative work environment, employees are empowered to thrive and contribute meaningfully to the company's success. Located in Canada, CORA offers a unique opportunity to be part of a dynamic team that values autonomy and fosters a supportive atmosphere for all its members.
We think you need these skills to ace Chief Technology Officer in Winnipeg
Technology Strategy Development
Cloud Architecture
Scalability
Performance Optimization
Security Standards
Software Development Leadership
Mentoring and Coaching
