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.
