Fractional CTO

Position Summary

The Fractional Chief Technology Officer (CTO) provides strategic and operational technology leadership to the company on a part-time basis. The role is responsible for ensuring that the company's technology strategy, hosting infrastructure, cybersecurity, and technical organization support the company's business objectives and long-term growth.

The role combines strategic technology leadership with practical oversight and is expected to provide clear direction, establish appropriate standards, mentor technical leaders, and address critical technology risks. This is not a purely advisory role. The Fractional CTO is expected to actively review technology decisions, participate in key technical discussions, and drive improvement initiatives while enabling the internal team to manage day-to-day execution.

Key Responsibilities

1. Technology Strategy and Leadership

• Develop and maintain the company's technology strategy and roadmap.
• Align technology priorities with business goals, product strategy, customer requirements, and growth plans.
• Advise executive management on major technology investments, risks, and opportunities.
• Evaluate emerging technologies and recommend those that can provide meaningful business or product value.
• Establish clear priorities for technical modernization, scalability, security, and operational improvement.
• Provide technology input for annual planning, budgeting, and strategic initiatives.

2. Ensure that systems are designed for scalability, performance, reliability, maintainability, and security.

• Provide oversight of application architecture, APIs, databases, integrations, and cloud or hosting infrastructure.
• Establish a practical architecture review and approval process appropriate for a small, agile software company.

3. Cloud, Hosting, and Infrastructure

• Provide strategic oversight of the company's hosting and cloud infrastructure.
• Review infrastructure architecture for availability, scalability, performance, security, and cost effectiveness.
• Establish appropriate standards for:
  • Cloud and hosting environments
  • Backup and recovery
  • Disaster recovery
  • Monitoring and alerting
  • Capacity management
  • Infrastructure security
  • Configuration management
• Review hosting and cloud costs and identify opportunities for optimization.
• Ensure that infrastructure supports customer service-level commitments and business continuity requirements.

4. Cybersecurity and Technology Risk

• Provide executive-level oversight of cybersecurity and technology risks.
• Establish a practical cybersecurity roadmap based on the company's size, products, customers, and risk profile.
• Review vulnerability management, patching, access controls, data protection, and incident response practices.
• Ensure appropriate security considerations are incorporated into software design and development.
• Support customer security assessments, audits, and technology due diligence when required.
• Ensure that significant technology and cybersecurity risks are clearly communicated to executive management.

5. Artificial Intelligence and Emerging Technologies

• Develop a practical strategy for the use of artificial intelligence within the company's products and operations.
• Identify high-value AI opportunities while avoiding technology adoption without a clear business case.
• Evaluate AI tools for software development, testing, analytics, customer support, and internal productivity.
• Provide guidance on AI architecture, data requirements, security, privacy, and governance.
• Support the development of AI-enabled product capabilities where commercially appropriate.

Expected Deliverables

The Fractional CTO is expected to produce and maintain practical deliverables, including:

• Technology strategy and roadmap
• Current-state technology and architecture assessment
• Cloud and hosting strategy
• Cybersecurity and technology risk roadmap
• AI and emerging technology strategy
• Technology organization and capability assessment
• Quarterly technology risk and progress report for executive management

Key Performance Indicators

Performance may be measured using a combination of the following indicators:

• Progress against the technology roadmap
• Reduction in critical technical risks
• Improvement in software quality and production stability
• Improvement in system performance and availability
• Improvement in cybersecurity maturity
• Optimization of cloud and hosting costs
• Development of internal technical leadership
• Successful implementation of strategic technology initiatives

Qualifications and Experience

• 15+ years of experience in software engineering and technology leadership.
• Previous experience as a CTO, VP of Engineering, Chief Architect, or equivalent senior technology leader.
• Experience working with small or mid-sized software product companies.
• Strong understanding of software product development and the complete software development lifecycle.
• Demonstrated experience with software architecture, cloud infrastructure, hosting, DevOps, cybersecurity, and technical operations.
• Experience leading or advising distributed software development teams.
• Ability to balance long-term technology strategy with immediate business and
• Strong understanding of Agile product development environments.
• Experience with AI and emerging technologies is preferred.
• Experience with B2B enterprise software and mission-critical customer systems is highly desirable.