Chief Technology Strategist Jobs (NOW HIRING)

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 AIs 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 companys 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.