Technology Health Check
A comprehensive diagnostic covering infrastructure, security posture, vendor contracts, and technology spend. Two weeks. Delivers a prioritized action plan your leadership can act on immediately.
Every engagement is structured around what your organization actually needs — not a standard package, not a staffing solution. Executive-grade technology leadership, delivered with discretion.
Monthly retainer engagements. Your organization's technology executive — on your terms, without the full-time cost.
Your retained technology executive. We own the roadmap, lead your vendors, oversee your team, and represent technology at the board level. The strategic leadership your organization needs — structured as a retainer, not a full-time hire.
Right for organizations where technology decisions are being made without senior accountability, where vendors are effectively managing themselves, or where the board is asking questions no one can currently answer.
Schedule a Confidential ConsultationDedicated cybersecurity leadership on a retained basis. We build and govern your security program, manage risk, maintain compliance, and deliver board-level reporting — without the cost of a full-time CISO.
Critical for family offices managing sensitive principal and financial data, and mission-driven organizations subject to donor data regulations, grant compliance, or audit scrutiny.
Discuss Your Security PostureFull-engagement executive coverage during a leadership transition. When your technology executive departs — planned or otherwise — we step in within days, stabilize operations, and maintain full momentum while you search for the right permanent hire.
Vendor negotiations, compliance obligations, board reporting, and active projects do not pause for executive transitions. Neither do we.
Talk Through Your TransitionDefined scope, clear deliverables, specific timeline. Many organizations begin here before moving to retained leadership.
A comprehensive diagnostic covering infrastructure, security posture, vendor contracts, and technology spend. Two weeks. Delivers a prioritized action plan your leadership can act on immediately.
A structured review of your security posture — gaps, vulnerabilities, compliance status, and remediation priorities. Essential before a board presentation, audit, or any significant vendor or data commitment.
Independent technology review for organizations evaluating an acquisition, major vendor relationship, or significant technology commitment. We surface what the other side's presentation does not.
A clear-eyed assessment of where your technology stands, where it needs to go, and a practical plan for getting there — aligned with your operating model, your team, and your budget.
An honest evaluation of your organization's cloud readiness — technical, operational, and financial. We identify the right strategy and a phased path that minimizes disruption and avoids unnecessary cost.
A practical assessment of where AI and automation can reduce operational overhead and improve outcomes in your specific environment — without the hype, without the unnecessary complexity.
Probably not. Most family offices and mission-driven organizations don't need a full-time CTO — they need the accountability, clarity, and strategic oversight one provides. A fractional engagement delivers exactly that, sized to what you need, at a fraction of the $300,000–$500,000 annual cost of a full-time hire.
We complement your existing team — legal counsel, wealth managers, auditors, IT staff. Our role is to be the senior technology voice in the room: translating technical decisions into strategic ones, holding vendors accountable, and ensuring your board has visibility into risk. We are not competing for relationships. We are making the whole advisory ecosystem more effective.
Every engagement is conducted under strict confidentiality. We maintain no public client list and reference no client relationships without explicit written consent. This is not a policy we adapted for your comfort — it is the standard under which we operate.
Completely independent. No reseller agreements, no vendor partnerships, no referral arrangements of any kind. We are retained by our clients and accountable to no one else. When we recommend a vendor — or recommend replacing one — it is because the recommendation serves you.
Fractional retainers typically begin within two to three weeks. Interim engagements — where a technology executive has departed — can begin within 48 hours. Fixed-scope assessments generally start within one week of agreement.
Fractional retainers are structured as monthly engagements, priced based on the scope and level of involvement your organization requires. Fixed-scope assessments are priced per engagement. We do not publish standard rates publicly because engagements are structured around what each client actually needs — not a package. The initial consultation is complimentary. If there is a fit, we will propose a structure and investment level that reflects your organization's specific situation.
A private, no-obligation call to discuss your organization's needs and whether Cavalier is the right fit.