Chief Technology Officer (Remote)

TAG Software Group is looking for an experienced Chief Technology Officer.

About Tag Software Group

TAG Software Group is a team of experienced investors and operators dedicated to acquiring, enhancing, and growing mission-critical software companies serving SMB, enterprise, and public sector customers.Founded as part of Valsoft Corporation, TAG provides a permanent home for software companies, we don’t buy to sell. Our focus is on long-term partnerships that protect your legacy, employees, and customers.

Our in-house team delivers an efficient, transparent, and seller-friendly process, ensuring speed and certainty of close. Once part of TAG, your company gains access to proven best practices, dedicated value-creation resources, and the extended ecosystem of our sister companies, including proprietary in-house technology including ValPay and Sadie AI — helping your business reach the next level.

Investment Approach

Unlike private equity and venture capital firms, we are Entrepreneurs who Buy, Enhance and Grow Software Businesses. That’s right; we don’t sell businesses. We form a strategic alliance with existing management teams. We recognize the dedication and perseverance required to create a firm and place a premium on customers’ and workers’ well-being over short-term goals.

Culture

Tag Software Group is more than just a place to work; we’re a team. We mean it when we say people are our greatest assets, so investing in them is our number one priority. We create an environment where our employees feel first-day-on-the-job excitement, day after day, creating a culture of high performers and collaboration. We celebrate our milestones, and we’re proud of them. We Dream Big, Stay Humble, and Stay Hungry.

The Role

Valsoft is looking for a hands-on and commercially minded Chief Technology Officer to lead the technology function of a SaaS platform business. This is a leadership role for someone who can operate strategically while staying close enough to the technology, architecture, and engineering practices to guide meaningful execution.

The platform is hosted on Microsoft Azure and supports a cloud-based architecture that includes microservices, event-driven design, Kubernetes, Azure Functions, Azure Logic Apps, App Service, PostgreSQL, and Azure SQL Server. The environment includes both modernization of an existing platform and continued development of new product capabilities.

The CTO will be responsible for leading the engineering organization, shaping the technical roadmap, improving delivery practices, and ensuring the platform can scale securely, reliably, and efficiently. This person will work closely with product, operations, and business leadership to align technology decisions with customer needs and commercial priorities.

The product roadmap includes integrating Generative AI and LLM capabilities into the platform. In parallel, the engineering team is already using AI-assisted development tools. A major part of the role will be to scale AI-driven development practices across the team, define practical guardrails, and ensure AI is used to improve productivity, quality, testing, documentation, and delivery speed without compromising engineering discipline.

The successful candidate will be an empathetic and structured leader with a track record of developing engineering talent while delivering measurable business outcomes. They should be comfortable making decisions using data, user insights, technical judgment, and product instincts. They must communicate clearly with stakeholders across the business and influence teams through clarity, accountability, and sound technical reasoning.

Key Responsibilities

• Lead and develop the engineering organization across architecture, software delivery, security, and operations.
• Define and execute the technology strategy in partnership with product and business leadership.
• Shape the technical roadmap to support platform modernization, scalability, reliability, product growth, and customer needs.
• Guide architectural decisions across cloud infrastructure, application architecture, data platforms, integration patterns, security, and operational resilience.
• Balance modernization, technical debt reduction, and delivery of new product capabilities.
• Support ISO 27001 readiness through secure development practices, technical controls, documentation, and audit support.
• Lead the integration of Generative AI and LLM capabilities into the product roadmap.
• Scale AI-driven development practices across engineering, building on existing developer usage.
• Define guardrails and quality standards for AI-assisted coding, testing, documentation, code review, and delivery workflows.
• Improve engineering productivity, delivery predictability, software quality, and operational maturity.
• Ensure effective use of project management, issue tracking, CI/CD, and version control tools such as JIRA, GitHub, or equivalent platforms.
• Partner with cross-functional leaders to align technical delivery with customer needs, commercial priorities, and operational requirements.
• Build clear team structures, responsibilities, development plans, and hiring priorities to support business growth.

About You:

• Bachelor’s degree in computer science, software engineering, or a related field.
• Minimum 3 years of experience managing software engineers.
• Minimum 5 years of progressive experience in technology leadership, software engineering, architecture, and full-stack development.
• Strong experience with SaaS product development and SaaS operating models.
• Mandatory experience implementing, scaling, or leading AI-driven development practices within software engineering teams, including hands-on use of AI-assisted development tools such as Claude Code, Cursor, or equivalent platforms to improve productivity, code quality, testing, documentation, and delivery speed.
• Practical experience with a combination of relevant technologies such as Microsoft Azure, .NET/C#, PostgreSQL, Azure SQL Server, Vue.js, Angular, Azure Functions, Azure Logic Apps, App Service, Kubernetes, microservices, event-driven architecture, or equivalent technologies.
• Experience leading modernization efforts, cloud-based platforms, or scalable software architecture.
• Experience with CI/CD, GitHub-based development workflows, Agile delivery, and modern software development lifecycle practices.
• Experience with ISO 27001, SOC 2, or similar compliance frameworks is an asset.
• Exposure to Generative AI, LLM integration, AI governance, or AI-enabled product development is an asset.
• Strong communication skills with the ability to work effectively with technical and non-technical stakeholders.
• Excellent written and spoken English.
• Legally authorized to work in Canada.

Employee Perks

•  Lead an established software company with the backing of a global acquisition group
•  High autonomy within a decentralized operating structure
•  Opportunity to shape and scale a business for long-term success
•  Career growth within a rapidly expanding, entrepreneurial ecosystem
•  Remote work flexibility (location-dependent)

We thank all applicants for their interest; however, only those candidates selected for an interview will be contacted.

We use AI‑assisted screening tools to support parts of the recruitment process, such as identifying relevant qualifications or matching skills to job requirements. All final hiring decisions are made by people. If you have questions about how AI tools are used or would like to request an alternative assessment method, please let us know.

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