Fractional CISOs, CIOs, and CTOs who embed with your team
Recommendations that get tracked through to done
Most executive advisory relationships end the same way: a deck, a handful of emails, then silence. A quarter later, everyone involved, the executive who made them included, is guessing about which recommendations were adopted, which stalled, and which sat untouched.
We treat advisory work as tracked work with a lifecycle of its own. Every recommendation your fractional executive makes is logged, given an owner, and carried through a status, proposed, in progress, or closed, as part of the same program record the Portal keeps for the rest of your engagement.
A recommendation register
Every recommendation your fractional executive makes is logged with an owner, so it stays visible long after the meeting ends.
A status you can see
Proposed, in progress, or closed. You should not have to ask your executive what happened to something they told you about last quarter.
A measured line in the QBR pack
Advisory activity is accounted for in the same quarterly package as the rest of your program, next to the operational work it drove.
Illustration: how a recommendation moves from proposed to closed, and where it lands in your QBR pack.
Available roles
Fractional CISO
Security program design, risk management, board reporting, and compliance oversight. The security leader your organization needs, at a fraction of the full-time cost.
Fractional CIO
Technology strategy, vendor evaluation, operational alignment, and digital transformation. Leadership that connects technology decisions to business outcomes.
Fractional CTO
Technical architecture, engineering team mentoring, product technology roadmaps, and build-vs-buy decisions. Strategic technical guidance from working operators.
Fractional CAIO
AI strategy, governance frameworks, responsible adoption, and integration planning. The Chief AI Officer role is emerging fast. Get ahead of it.
What your fractional executive does
Security program design
Build the program from the ground up: policies, controls, incident response, and compliance alignment.
Board & investor reporting
Clear, confident security and technology updates that satisfy board-level scrutiny and investor due diligence.
Technology roadmaps
Strategic plans that align technology investments with business goals. Prioritized, budgeted, and actionable.
AI strategy & governance
Framework for evaluating, adopting, and governing AI across your organization. Policy, risk, and integration.
Team mentoring
Level up your internal team. We transfer knowledge so your organization builds lasting capability of its own.
Vendor evaluation
Objective assessment of technology vendors. We evaluate against your requirements alone.
Engagement models
Credit-based
Purchase a block of credits. Use them for any combination of strategic leadership, project work, and operational support. Maximum flexibility.
Retainer
Dedicated hours per month with a named fractional executive. Consistent presence, deep context, and predictable cost.
Hours per month
Structured engagement with defined scope and deliverables. Ideal for specific initiatives like SOC 2 preparation or board reporting.
Why companies choose Cloud Sentry for security leadership
A CISO is only as strong as the team behind the title.
Pure vCISO firms
Independent vCISO firms
- ✓Experienced security executives
- ✓Board-level reporting and strategy
- ×Advise only. Don’t build or operate anything
- ×Client still needs an MSP, a cloud team, and a compliance tool
- ×Three more vendors to fill the gaps
They tell you what to do. You still need to find someone to do it.
Big consulting firms
Big-four consulting firms
- ✓Deep expertise and recognized brand
- ×Built for enterprises with $10M+ security budgets
- ×Six-month assessments that stop at a report
- ×Hourly rates that burn through budgets fast
- ×Operations end with the engagement, leaving you to carry it
Advice priced for companies ten times your size. It ends in a report.
Cloud Sentry
The CISO + the team that executes
- ✓Fractional CISO who sets strategy and reports to the board
- ✓The operations team that implements every recommendation
- ✓Security program built, running, and documented
- ✓Scales from a few hours/month to near full-time
- ✓One vendor covers the whole scope
- ✓Every recommendation tracked to a status and rolled into your QBR pack
Advisory and execution in one. The fractional exec comes with the team.
Sound familiar?
“Our board is asking about security and nobody can answer.”
A fractional CISO gives your board confident, structured security reporting backed by a real operational program.
“We need a CISO for SOC 2 but can't afford a full-time hire.”
A fractional CISO at a fraction of the cost, with the execution team to actually build what the auditor expects.
“Our technology decisions are getting ahead of any roadmap.”
A fractional CTO or CIO builds the roadmap, evaluates vendors, and aligns technology investments with business goals.
AI governance is the next compliance frontier
Companies adopting AI face new questions: What data are we training on? Who's accountable for AI decisions? How do we demonstrate responsible use to customers and regulators?
Our Chief AI Officers help companies adopt AI responsibly: policy, risk assessment, and integration strategy designed for your specific business context.
AI usage policy and acceptable use frameworks
Risk assessment for features built on AI
Data governance for training and inference
Vendor evaluation for AI tools and platforms
Board-level AI strategy and reporting
The team inside
The people who run this with you.
Named operators, reachable in the portal, answering you directly.
Dirk Vander Noot
Co-Founder & Operating Partner
Jason Bowen
Cloud Operations Specialist
Ken Hanson
Founder & CEO
John May
Fractional CIO & Advisor
Emil Diaz
Fractional CTO
Board-ready, on demand
The program is running, and you can show it.
Your fractional executive sets the strategy, and the platform is where the work shows up: the live state of the security program, the evidence behind it, and a board-ready view you can pull whenever you are asked. A running program you can see, ready before anyone asks.
Leadership that operates.
Tell us what role you need. We'll match you with a fractional executive who brings the team to get it done.
Published structure with a written annual escalator cap. Read the whole page before anyone calls you.
Executive leadership works best next to the team that executes. The partnership runs both, end to end, under one accountable lead.