Chief Information Officer

GuidePoint Security is a leading boutique cybersecurity firm specializing in value-added resale of security solutions and delivery of professional services across all areas of information security. With over 1,200 employees nationwide and a primarily remote workforce, GuidePoint combines deep technical expertise with a vendor-agnostic approach to help clients address today's most complex cybersecurity challenges.

Role Summary

GuidePoint is seeking a strategic, execution-driven Chief Information Officer (CIO) to lead all facets of the organization’s information technology and systems. The CIO oversees the planning, development, implementation, and maintenance of enterprise IT systems, ensuring they support business operations, efficiency, security, and growth. This role serves as the key executive liaison between IT and other business units, aligning technology initiatives with the organization’s strategic goals. This is a senior executive role reporting directly to the CEO and working closely with the COO and CISO to ensure IT is a true business enabler in a complex, fast-growing, and security-first organization.

Key Responsibilities

• Strategic IT Leadership

  • Define and execute a forward-thinking IT strategy aligned with GuidePoint’s growth, with a technology-first mindset and strong emphasis on AI adoption and enablement.

  • Collaborate with executive leadership to prioritize, fund, and deliver digital transformation initiatives that improve operational effectiveness and scalability.

  • Identify emerging technology trends and assess their impact on the organization.

  • Provide direction and thought leadership on digital transformation and innovation initiatives.

• Internal Stakeholder Engagement

  • Build trusted partnerships across the business, especially with the COO and functional leaders, to understand needs and deliver tailored solutions.

  • Maintain a strong internal executive presence as a visible and credible leader of IT strategy, delivery, and innovation.

  • Communicate IT performance and strategic plans to the executive team and board.

• Operational Excellence & Service Delivery

  • Oversee the daily operations of the IT department, ensuring optimized work throughput, backlog management, and service delivery across a decentralized and rapidly evolving environment.

  • Ensure the availability, integrity, and performance of all IT systems and platforms.

  • Establish and maintain metrics and accountability systems to ensure responsiveness, transparency, and continuous improvement.

  • Drive consolidation of redundant platforms to streamline operations and reduce overhead.

• Team & Budget Management

  • Build and lead a high-performing IT team, promoting continuous learning and professional development.

  • Oversee IT infrastructure, help desk, enterprise applications, business intelligence, AI teams, and operations.

  • Develop and manage IT budgets, vendor relationships, and strategic sourcing to ensure high ROI.

• Security & Compliance Collaboration

  • Partner with the CISO to align on overlapping domains such as email security, endpoint protection, and identity management.

  • Support the operationalization of compliance requirements impacting IT (e.g., privacy, access controls, data retention).

  • Collaborate with legal, compliance, and risk teams on audits and data protection initiatives.

Qualifications & Experience

• Bachelor's degree in Information Technology, Computer Science, Business Administration, or related field (Master's preferred).

• 10+ years of progressive experience in IT leadership roles, including at least 5 years at the senior executive level.

• Proven success leading IT organizations of similar size and complexity, ideally within a high-growth, services-oriented, or cybersecurity-adjacent company.

• Demonstrated ability to manage large-scale transformation efforts including AI integration, data governance, and platform consolidation.

• Strong knowledge of IT systems, infrastructure, cybersecurity, and emerging technologies with deep experience in SaaS-based environments.

• Deep understanding of cybersecurity principles, including infrastructure and application security controls, with experience implementing secure architectures across SaaS and hybrid environments.

• Track record of improving operational maturity, delivery timelines, and cross-functional transparency.

• Strong leadership, communication, and stakeholder management capabilities.

• Ability to translate complex technical concepts into business language.

• Collaborative and consultative partner with the ability to influence and lead across functional areas

• Excellent strategic thinking, problem-solving, and decision-making skills.

• Financial acumen and experience managing multi-million-dollar IT budgets and vendor portfolios.