Boutique Technology Advisory · Est. Tampa Bay
Senior technology counsel.
For the decisions that move the business.
Fractional CTO, CIO, and CISO leadership — plus M&A technology due diligence and compliance readiness when the work calls for project engagement. Vendor-independent. Senior-led. Built on decades of operating experience across regulated industries.
The Cavalier Practice
Built on three commitments: clear scope before contract, three written options on every engagement, and the same senior advisor from the first call through the final review.
Boutique by designWhat we do, in plain English
The fractional executive your organization actually needs.
Cavalier Consulting is a boutique advisory firm that provides senior technology leadership — Chief Technology Officer, Chief Information Officer, and Chief Information Security Officer — to mid-market organizations on a fractional basis. We serve companies between 25 and 500 employees where technology decisions now carry strategic weight, but a full-time C-suite hire is the wrong size for the business.
Our work covers technology strategy and roadmap, IT and operations leadership, cybersecurity and compliance (SOC 2, HIPAA, CMMC), M&A technology due diligence, and post-acquisition integration. We are vendor-independent: no managed services, no implementation, no referral fees, no reseller agreements. We get paid to be right.
Our senior advisors are headquartered in Tampa Bay and serve clients in person across the U.S. — particularly New York, Washington D.C., and Boca Raton — with engagements nationwide. Engagements start at $4,500 per month and are scoped to the outcomes the work is built around, presented as three written options in every proposal.
Why Cavalier
Four things that make this work.
These are not promises. They are the structural decisions that shape every engagement — and the reasons our clients call us instead of the alternatives.
Senior-only delivery, end to end
Every Cavalier engagement is led by a senior advisor with decades of operational experience. When the engagement calls for specialized depth — a senior security architect for CMMC technical controls, a senior cloud economist for AWS cost work — we deploy vetted specialists from a curated network, working under firm methodology. No bench rotation. No junior staff. No partner-sells-and-analyst-delivers.
CTO · CIO · CISO under one firm
Most fractional firms specialize in one role. We deliver all three. Technology strategy, IT operations, and information security are decisions that move together — treating them in isolation is how organizations end up with strategy that ignores security risk, or security spend that doesn't fit the technology direction. One firm. One methodology. One coherent direction.
Vendor-independent. Pure advisory.
We do not sell software. We do not resell hardware. We do not run managed services. We do not take vendor referral fees or partner kickbacks. We do not compete with the implementation firms we recommend. Every recommendation is filtered through one question — is this the right answer? — never through how to expand the engagement.
Value-based fees. Written outcomes.
We work to a disciplined methodology: engagements scoped to defined outcomes, fees based on the value of those outcomes, three written proposal options on every engagement. You see the methodology. You see the deliverables. You see the price. No hourly billing games. No scope-creep arguments. No surprise change orders.
Services
Three roles. One engagement. One coherent direction.
Most fractional firms specialize in one role. We deliver all three under one engagement, because the decisions move together.
Fractional CTO
Technology strategy, architecture decisions, build-versus-buy, and engineering leadership for organizations where product and platform are now central to the business but a full-time CTO is the wrong size.
Explore the role Chief Information OfficerFractional CIO
IT operations, vendor governance, cloud and SaaS strategy, M&A integration, and the unglamorous work of making technology actually serve the business. Strategy that translates into accountable execution.
Explore the role Chief Information Security OfficerFractional CISO
Cybersecurity strategy and program leadership. SOC 2, HIPAA, CMMC, ISO 27001 readiness. Board-level risk communication. Incident response preparedness. Insurance and compliance posture that holds up under scrutiny.
Explore the roleIndustries we know
Where decades of regulated-industry experience matter.
Our senior advisors have led technology and security programs through SEC scrutiny, OCR investigations, DoD audits, and the diligence pressure of mid-market PE exits.
Private Equity
Portfolio company technologyPre-exit tech remediation, post-acquisition integration, technology due diligence under deal timelines. We work directly with operating partners.
Explore the practice II.Financial Services
Fintech, RIAs, SOC 2Regulatory pressure, vendor risk, and audit-ready posture for fintechs, RIAs, broker-dealers, and the boards that govern them.
Explore the practice III.Healthcare
HIPAA, OCR, EHR strategyHIPAA-grade security leadership and EHR-aware technology strategy for practices, networks, and life-sciences companies between 15 and 500 employees.
Explore the practice IV.Defense Industrial Base
CMMC 2.0, DFARS 7012, DoD contract retentionCMMC Level 2 and Level 3 readiness from advisors who read the regulation, not the checklist. Built around DoD contract retention — not certification theater.
Explore the practice V.Professional Services
Law, accounting, A&ESenior technology leadership for partnerships where the partners have been the IT committee — and that arrangement has reached the limits of what it can do.
Explore the practice
How we work
Outcomes first. Fees scoped to value, not hours.
A disciplined boutique methodology. Engagements are scoped around defined outcomes. Fees are tied to the value of those outcomes — not billable time. Every proposal arrives as three written options at different scopes, so the conversation is about what shape the business needs, never about negotiating an hourly rate down.
- i.
The fit call
Twenty minutes. We listen. You ask anything. If we are not the right fit, we say so on the call and refer you to firms we trust. No diagnostic work. No homework. No nurture sequence.
- ii.
Three written options
Within five business days, three engagement options — different scopes, different price points, different outcomes — so you pick the right size for the business, not what we want to sell.
- iii.
Documented outcomes
Outcomes go in writing before the contract is signed. The engagement is scoped around them. The 30- and 60-day reviews are structured against them. No moving goalposts.
- iv.
Senior delivery
Every engagement is led by a senior advisor. Specialists from our curated network join when the work calls for it. Same methodology, every engagement, every time.
What we do not do
The shortest sales conversation in consulting.
If you came looking for any of the items at right, we are not the right firm — and we'll tell you so on the first call. That is the boutique advisory commitment: clarity about fit before clarity about fee.
Every recommendation we make is filtered through one question: is this the right answer? Not how to expand the engagement. Not which vendor pays a referral. Not what fills a bench.
- × Managed IT services We do not run help desks, monitor endpoints, or provide ongoing IT operations support.
- × Implementation work We do not write code, install hardware, configure infrastructure, or do hands-on-keyboard delivery.
- × Software or hardware resale No reseller agreements. No volume discounts we mark up. No vendor referral fees.
- × SOC 2 or CMMC audits We prepare you for the assessor. We do not perform the audit itself — audit firms must be independent.
- × Staff augmentation We are not a marketplace, a bench, or a staffing firm. You get senior advisors, not contractors.
- × Hourly engagements Every engagement is scoped to outcomes and priced on value. No time sheets. No surprise overruns.
Frequently asked
Questions worth answering before the call.
Most of the questions we field on the first call are answered here. If yours isn't, schedule a fit call and we'll answer it.
What is Cavalier Consulting?
Cavalier Consulting is a boutique technology advisory firm. We provide fractional Chief Technology Officer (CTO), Chief Information Officer (CIO), and Chief Information Security Officer (CISO) leadership to mid-market organizations — typically 25 to 500 employees — where technology is now decisive but a full-time hire is the wrong shape for the business.
We are vendor-independent: no managed services, no implementation, no reseller agreements, no referral fees. We get paid to be right.
Who is the typical Cavalier client?
Our clients are CEOs, COOs, managing partners, and private equity operating partners running organizations between $5M and $500M in revenue. They are most often in private equity portfolio companies, financial services and fintech, healthcare and life sciences, defense industrial base, and professional services (law, accounting, A&E).
What they share: technology has become material to the business — strategy, security, regulatory exposure, or all three — and they need senior advisory judgment, not another vendor with something to sell.
How is Cavalier different from other fractional CTO firms?
Three things separate us. First, we deliver all three roles — CTO strategy, CIO operations, and CISO security — under one firm. Most fractional firms specialize in one. Treating them in isolation is how organizations end up with technology decisions that contradict their security posture.
Second, we are pure advisory. We do not sell software, resell hardware, take vendor referral fees, run managed services, or compete with the implementation partners we recommend. Our advice is not filtered through a question about how to expand the engagement.
Third, we work to a disciplined boutique methodology: value-based fees scoped to the outcomes the engagement is built around, three written proposal options on every engagement, and senior-only delivery. No bench rotation. No junior staff. No partner-sells-and-analyst-delivers.
Where does Cavalier work?
Our home market is Tampa Bay. Our senior advisors serve clients in person across the U.S. — we are particularly active in New York, Washington D.C., and Boca Raton, with engagements ongoing nationwide. We deliver through a hybrid model: structured remote cadence with on-site presence for board meetings, executive offsites, M&A diligence, and major program milestones. Travel is billed at cost, no markup.
How much do Cavalier engagements cost?
Engagements start at $4,500 per month. Specific fees are determined by the outcomes the engagement is scoped around and are presented as three written options in every proposal. Project engagements (technology assessments, due diligence, CMMC readiness, SOC 2 readiness) are priced as fixed-fee programs against defined deliverables.
We publish a floor, not a ceiling, deliberately. Our fees are scoped to value, not hours.
How long is a typical engagement?
Retainers begin at three months for the Advisory tier; six months for Standard, Executive, and Enterprise tiers. Project engagements range from two weeks (M&A technology diligence) to six months (CMMC Level 2 readiness). Many engagements that begin as projects continue as retainers once the immediate work is complete.
What does Cavalier NOT do?
We do not provide managed IT services. We do not write code or stand up infrastructure. We do not staff help desks. We do not resell software or hardware. We do not take vendor referral fees. We do not perform SOC 2 or CMMC audits (we prepare you for the auditor). We do not compete with the implementation firms we recommend — we work alongside them.
If what you need is implementation muscle, an MSP, or a staff augmentation partner, we will tell you on the first call and refer you to firms we trust.
How do I start?
Schedule a 20-minute fit call. It is exactly what it sounds like: a fit conversation, not a sales pitch, not a free diagnostic. We spend ten minutes understanding your situation. You spend ten minutes asking us anything you want. If there is fit, we send three written proposal options within five business days. If there is not, we tell you on the call and refer you to firms we trust.
Ready to put senior technology leadership to work?
Twenty minutes. We listen. If we are the right fit, we send three written proposal options within five business days. If we are not, we refer you to firms we trust.