About the role
Overview We are seeking an experienced, business-minded technology leader to serve as a Fractional CTO or Technology Strategy Advisor across a portfolio of clients. This role combines high-level strategic leadership with practical execution — guiding organizations through technology transformation, operational scaling, and digital enablement. Engagements may include ongoing fractional CTO retainers, steering committee participation (SCaaS), or short-term advisory work. The right candidate thrives in a dynamic, consultative environment and is comfortable shifting between boardroom strategy and hands-on technical problem solving. Engagement Model Can be structured as: • Full-Time Employee (FTE) role leading multiple client engagements; or • 1099 Subcontractor on a fractional retainer basis (typically X hours/week per client). Compensation and structure will depend on experience, availability, and client portfolio alignment. Core Responsibilities Strategic Leadership & Governance - Serve as a technology leader on client steering committees, providing oversight, insight, and alignment between business strategy and technology investment. - Develop, evaluate, and refine technology roadmaps that enable growth, efficiency, and scalability. - Act as an executive advisor to CEOs, COOs, and Boards on technology decisions, vendor selection, and digital transformation. - Build and mentor internal technology leadership — particularly in scenarios where a client is transitioning or developing an internal CTO or Director of Technology. Operational & Technical Guidance - Assess and optimize client technology stacks, development practices, infrastructure, and security posture. - Guide project management, software architecture, and engineering process improvement initiatives. - Lead technology due diligence and integration for M&A, investment, or partnership scenarios. - Oversee or advise on vendor and partner relationships to ensure accountability and value. AI, Automation & Efficiency - Integrate practical AI and automation initiatives that drive measurable improvements in efficiency, scalability, and process optimization — not AI for AI’s sake. - Help define responsible AI policy and governance within client organizations to ensure compliance, ethics, and alignment with operational goals. Team Leadership & Mentoring - Coach and mentor emerging technology leaders, helping bridge skill gaps during leadership transitions or growth phases. - Support hiring, team structure, and culture development within client technology organizations. Qualifications - Proven experience in technology or operational leadership — ideally as a CIO, CTO, IT Director, or in an equivalent executive role where technology strategy and execution were a core part of daily responsibility (e.g., COO, CFO, or CEO in a technology-dependent organization). - Proven success aligning technology strategy with business outcomes. - Strong understanding of modern software architecture, cloud infrastructure, data strategy, and cybersecurity fundamentals. - Demonstrated experience implementing automation, analytics, and/or AI-driven process improvements. - Exceptional communication and stakeholder management skills, comfortable engaging with executive leadership and non-technical stakeholders. - Consulting, advisory, or multi-client fractional experience strongly preferred. Attributes of the Ideal Candidate - Operates as a strategic partner, not just a technologist. - Brings a pragmatic, outcomes-driven approach — balancing innovation with operational discipline. - Excels in fractional or portfolio-style work and context-switching between clients. - Enjoys coaching and developing leaders, not just running teams. - Has a bias toward efficiency, scalability, and measurable business impact. Example Engagement Scenarios - Long-term fractional CTO supporting a mid-market company’s ongoing digital transformation. - Short-term interim CTO following leadership turnover. - Coaching engagement for an internal CTO recently promoted into the role. - Steering Committee member advising on enterprise technology strategy and AI enablement.