Fractional CTO / Technology Leader

A professional services firm is seeking a fractional CTO or technology leader to reduce reliance on individual leaders, modernize infrastructure, and advance customer relationship management, workflow automation, and AI adoption. This part-time leader will assess the current technology environment, guide a move from internally hosted systems to managed or cloud services, shape CRM and workflow strategy, and help recruit and mentor the next full-time technology hire. Local candidates are preferred; the role may transition into an ongoing advisory relationship after the initial engagement.

Responsibilities

• Assess the current technology stack, architecture, security posture, and operational gaps.
• Develop and own a practical, prioritized technology roadmap aligned with business goals.
• Lead cloud migration strategy and execution to move systems to a managed or cloud environment.
• Drive CRM and workflow strategy and implementation, including coordinating a CRM transition and evaluating or implementing an operational platform.
• Identify, design, and implement automation and AI opportunities to reduce manual work and improve efficiency.
• Partner with founders and business stakeholders to define technical requirements, KPIs, and success measures.
• Interview, source, and help hire the next full-time technology leader; provide mentoring and support a smooth handoff.
• Mentor and upskill existing IT staff; establish standard operating procedures, documentation, and runbooks.
• Manage vendors, contractors, and third-party integrations; support reliable production operations and incident response.
• Recommend and manage technology budgets, vendor contracts, and cost optimization measures.
• Ensure appropriate data protection, privacy, compliance, and security controls for sensitive client information.

Qualifications

• Proven experience as a CTO, VP of Engineering, Head of Technology, or senior technology leader, ideally in a small business, professional services, or consumer-facing organization.
• Demonstrated experience with CRM implementations and workflow automation.
• Hands-on technical background with modern application technologies and cloud platforms.
• Track record of executing cloud migrations and retiring internally hosted infrastructure.
• Practical experience identifying and implementing automation and AI solutions that reduce manual processes.
• Experience recruiting, hiring, and mentoring engineers and technical staff.
• Strong vendor and stakeholder management skills, with the ability to translate business needs into technical strategy.
• Familiarity with data security, privacy, and compliance requirements for organizations handling sensitive client information.
• Comfortable working in a founder-led, growth-oriented environment and reducing single points of failure.