Overview

Our client is seeking an experienced Virtual Chief Technology Officer (CTO) to guide small and medium-sized businesses through the process of exploring cloud solutions and planning technology migrations. This role is ideal for a strategic technologist who understands both business goals and technical execution — helping organizations transition from outdated systems to modern, secure, and scalable digital environments.

You’ll act as a trusted advisor, designing cloud strategies, assessing readiness, and building transformation roadmaps that align with each client’s goals and resources.

Key Responsibilities

• Conduct cloud readiness assessments for small businesses using a structured framework.

• Recommend technology stacks (Microsoft 365, Azure, AWS, or Google Cloud) tailored to business needs.

• Develop cloud migration roadmaps with clear milestones, timelines, and budgets.

• Evaluate existing on-premise systems and create modernization strategies.

• Advise on security, data protection, and compliance best practices during cloud adoption.

• Work collaboratively with client leadership and technical teams to ensure smooth implementation.

• Support clients in selecting vendors, tools, and managed service options.

• Provide executive-level reporting and ongoing technology guidance.

Ideal Candidate

• 7+ years of experience in IT architecture, cloud strategy, or digital transformation.

• Deep understanding of Microsoft Azure, Microsoft 365, and modern workplace environments.

• Experience working with small to mid-sized organizations or startups.

• Strong communication skills, able to translate technical concepts into business outcomes.

• Proven ability to develop transformation plans, manage stakeholder expectations, and deliver measurable value.

• Certifications such as Azure Solutions Architect, AWS Certified Solutions Architect, or CompTIA Cloud+ are a plus.

Time Commitment

• Part-time: Up to 10 hours per week (flexible schedule)

• Remote work

• Initial engagement: 3-month contract with extension opportunities

Deliverables

• Cloud readiness and digital maturity assessment

• Migration strategy and roadmap

• Technology recommendations report

• Executive summary presentation for business owners

Why Work with Us

Our client provides digital transformation and cloud advisory services designed to empower small and minority-owned businesses. You’ll be working within a purpose-driven ecosystem that values innovation, inclusion, and impact — helping entrepreneurs adopt technology that fuels real growth.