Services
Advisory and leadership for critical technology work
Engagement models designed for organizations that need experienced technology direction, without adding permanent executive headcount.
Fractional CIO Advisory
What it is
Senior CIO-level technology leadership on a flexible, part-time or interim basis. We step in as your technology executive, providing direction, governance, team leadership, and strategic planning without the overhead of a full-time hire.
Where it helps
Organizations that have outgrown basic IT support but are not ready for a full-time CIO. Companies navigating growth, transition, or leadership gaps. Boards and investors needing independent technology assessment.
Example outcomes
- Clear technology strategy aligned to business objectives
- Improved IT governance and decision-making discipline
- Stronger vendor and technology portfolio management
- Executive-ready communication and board reporting
Cybersecurity Advisory & Compliance
What it is
64thSquare provides cybersecurity leadership in two modes depending on what the organization needs. For organizations without a dedicated security leader, we serve in a Fractional CISO capacity, providing ongoing program leadership, risk governance, and executive-level security direction. For organizations with a specific compliance, audit, or readiness challenge, we deliver targeted advisory, risk assessment, gap analysis, remediation planning, and compliance evidence preparation.
Where it helps
- Organizations without dedicated security leadership needing ongoing program direction
- Companies responding to audit findings, compliance requirements, or a security incident
- Firms preparing for SOC 2, ISO 27001, PCI DSS, or regulatory examination
- Boards and leadership teams needing an independent security posture assessment
Example outcomes
- Risk-prioritized security program aligned to actual business risk tolerance
- Improved security maturity without tool sprawl or unnecessary spend
- Compliance documentation and evidence readiness for relevant frameworks
- Clear incident response structure and governance ownership
- Independent assessment delivered to board or executive leadership
Technology Transformation
What it is
End-to-end transformation planning and execution support. From assessing current state and defining target architecture through building roadmaps and guiding delivery, with a focus on outcomes, governance, and organizational readiness.
Where it helps
Organizations undertaking significant technology change, cloud migration, ERP modernization, digital platform builds, or operating model redesign. Companies that need experienced direction to avoid common transformation pitfalls.
Example outcomes
- Realistic, sequenced transformation roadmap
- Governance structures that maintain momentum
- Organizational change management integrated with delivery
- Measurable business outcomes at each stage
Program Recovery & Execution
What it is
Rapid assessment and intervention for technology programs that are off track. We diagnose root causes, stabilize the situation, and establish the discipline needed to deliver. Direct, practical, and focused on restoring confidence.
Where it helps
Programs experiencing schedule overruns, budget pressure, scope creep, or team dysfunction. Organizations that need an independent assessment of program health. Leadership teams needing a credible path forward.
Example outcomes
- Honest assessment of program status and recovery options
- Stabilized delivery with clear accountability
- Restored stakeholder and team confidence
- Disciplined execution through to completion
AI-Enabled Transformation
What it is
Practical advisory for identifying and implementing AI-enabled use cases that improve productivity, decision-making, risk management, and business execution. We help organizations cut through the noise and focus on high-impact AI opportunities that deliver measurable results.
Where it helps
Organizations exploring how AI can improve operations, customer experience, or competitive position. Companies that need practical guidance on AI adoption without over-investing in unproven technology. Teams seeking to build AI capabilities pragmatically.
Example outcomes
- Identified high-impact AI use cases aligned to business priorities
- Practical roadmap for AI adoption and capability building
- Improved productivity and decision-making through AI-enabled tools
- Risk-managed approach to AI implementation and governance
How we engage
Flexible by design
64thSquare engages on a retainer or project basis depending on the nature and duration of the work.
Retainer
Retainer engagements are suited to fractional CIO or CISO roles, ongoing advisory relationships, and programs requiring sustained senior involvement over multiple months. Retainer terms are structured around specific time commitments and defined outcomes, not open-ended hour banks.
Project
Project engagements are suited to bounded advisory work: program health assessments, cybersecurity gap analyses, technology due diligence, transformation roadmaps, and similar defined-scope deliverables with a clear beginning and end.
All engagements begin with a no-commitment conversation to establish fit, scope, and approach. If 64thSquare is not the right resource for a given situation, we will say so.
Need senior technology leadership for a project, transition, recovery effort, or advisory role?
Schedule a confidential conversation to discuss how 64thSquare can help your organization.