Retained executive counsel, independent strategic advisory, or a targeted fixed-scope engagement. Every service is structured around measurable outcomes and calibrated to what your family office or portfolio company actually needs — never to a packaged scope.
Cavalier Consulting offers three categories of engagement: retained counsel (fractional CTO, fractional CIO, fractional CISO, and interim executive coverage on monthly retainer); strategic advisory (technology governance, AI governance, vendor selection, and technology due diligence for acquisitions); and fixed-scope assessments (Technology Health Check, Cybersecurity Baseline, Cloud Readiness, AI & Automation Scan, Vendor Contract Optimization, IT Budget & Spend Analysis). All engagements are vendor-independent, senior-led, and conducted under strict confidentiality.
Monthly retainer engagements. Your technology executive on your terms — structured around access, governance, and outcomes rather than hours.
Your retained technology executive. We own the roadmap, govern your vendor relationships, represent technology at the board or family council level, and ensure the senior operational leadership of your organization always has a technology counterpart in the room.
The depth and accountability of a full-time hire, structured as a retainer — appropriate for family offices and portfolio companies that need senior oversight without the cost, complexity, and organizational footprint of a full-time executive.
Dedicated cybersecurity governance on a retained basis. We build and govern the security program, manage risk, maintain compliance posture, and deliver board-level reporting — without the cost or complexity of a full-time CISO hire.
Essential for family offices where a breach is not a statistic but a family event, and for portfolio companies where a cybersecurity incident affects the sponsor, the family office, and the operating business simultaneously.
When a technology executive departs — planned or otherwise — the cost of a leadership gap can be severe. Vendor negotiations stall. Compliance deadlines slip. Active projects lose momentum. We step in within days, stabilize the technology organization, and maintain full continuity while you conduct the search for a permanent hire.
Project-based strategic advisory for family offices and portfolio companies with specific decisions to make — vendor selections, architecture planning, cybersecurity programs, AI governance, organizational design. Independent perspective, business-aligned outcomes, and a final deliverable that holds up to board-level scrutiny.
Independent technology assessment for family offices and sponsors evaluating an acquisition, a major vendor commitment, or a portfolio company's current state. We surface what the other side's presentation does not — technical debt, cybersecurity exposure, scalability limits, key-person risk, and vendor commitments — before a commitment is made that cannot easily be unwound.
Defined scope, clear deliverables, specific timeline. Many client relationships begin here before moving into a retained counsel arrangement.
Comprehensive diagnostic covering infrastructure, security posture, vendor contracts, and technology spend. Delivers a prioritized action plan in two weeks.
Structured review of security posture — gaps, vulnerabilities, and remediation priorities. Appropriate before a board presentation, an audit, or a major data-handling commitment.
Technical, operational, and financial evaluation of cloud readiness. A phased migration path that minimizes disruption and avoids unnecessary cost.
Practical assessment of where AI and automation can reduce operational overhead — and where the hype does not survive contact with the environment.
Independent review of your technology vendor agreements. We identify overspend, unfavorable terms, and opportunities to renegotiate or consolidate.
Line-by-line review of technology expenditure against organizational needs. Find the waste before it compounds into next year's budget baseline.
A private, no-obligation conversation to discuss your organization's needs and whether Cavalier is the right fit.
Schedule a Confidential Consultation