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vCISO Services:
A Fractional CISO Accountable to Your Board
A named security leader who owns your program, answers examiners, insurers and LPs, and reports progress every quarter.
On retainer, or as a fixed-scope Jumpstart CISO engagement that audits, analyzes, recommends and reports back in a quarterly business review.
Most companies have a security stack. Few have someone accountable for it.
A vCISO turns tools, policies and vendors into one program with an owner, a roadmap and a report your board can read.
What is a vCISO?
A vCISO, or virtual chief information security officer, is a senior security leader who does the CISO job for your company on a part-time or project basis. The job is the same as a full-time CISO's: own the security program, decide what gets fixed first, set policy, oversee vendors, and report risk to leadership and the board. What changes is the hours. You get the accountability without a full-time executive hire.
You will also see the role called a fractional CISO, a virtual CISO or CISO as a service. The names are used almost interchangeably. "Fractional" usually means a set share of one named person's time. "CISO as a service" sometimes means a team behind a ticket queue. At Cloudskope it means one named leader: our founder.
Breach costs keep rising, and so do the questions from regulators, insurers, investors and customers. Most mid-market companies cannot justify a full-time CISO, but every one of those questions still needs an owner. That gap is what a vCISO fills.
vCISO vs full-time CISO vs MSP
A vCISO does not replace your MSP. It gives your MSP a security leader to answer to. For background, read What is a vCISO?, What is a fractional CISO? and What is CISO as a service?
When You Need a vCISO
Most companies do not need a full-time CISO. They need one at the moments someone asks who owns security.
These are the moments that usually trigger the call.
An Exam or Regulator Request
Amended Reg S-P, Reg S-ID and the FTC Safeguards Rule all expect named responsibility and written evidence that controls work.
Your vCISO owns the program and keeps the evidence file current, so an exam request is a download, not a scramble.
LP, Lender and Board Questions
LPs, lenders and boards ask who is accountable for cybersecurity and how often they report. "Our MSP handles it" does not survive a follow-up question.
Your vCISO answers the questionnaire and sits in the meeting.
Cyber Insurance Renewal:
Answers You Can Prove
Carriers rely on your answers about MFA, backups, endpoint protection and payment controls. A wrong answer can put a claim at risk.
Your vCISO checks each answer against the actual settings before anyone signs.
Acquisitions and
the 100-Day Plan
After close, someone has to turn diligence findings into a funded plan, bring the acquired environment up to standard and report progress to the sponsor. That is a vCISO's job, not the IT help desk's.
Customer Security Reviews:
Questionnaires and SOC 2
Security questionnaires, SOC 2 readiness and contract security terms move faster with one person who knows the environment and can stand behind the answers. Slow security reviews stall revenue.
After a Breach or Failed Audit
Someone has to own the root-cause fixes, rebuild trust with the board and the insurer, and make sure the same gap does not reopen next year.
What Your vCISO Owns
A vCISO is not a consultant who hands you a report.
It is a security leader who owns these six areas, makes the decisions inside them, and reports on them every quarter.
Security Program & Roadmap
One plan, one owner, one budget.
We set the security strategy, prioritize what gets fixed first, and turn it into a 12-month roadmap with owners, dates and a budget leadership can approve.
Without a roadmap, security spend follows the last vendor pitch or the last scare. A plan ties every dollar to a risk it reduces.
Security Strategy
12-Month Roadmap
Budget and CapEx Forecast
Program Metrics
Risk Register & Board Reporting
Risk in business terms.
We keep a live risk register, score exposure across confidentiality, integrity and availability, and present it to leadership and the board each quarter.
Boards are expected to oversee cyber risk. They can only do that with a clear view of what is exposed, what it could cost and what is being done about it.
Live Risk Register
CIA Triad Scoring
Board and Committee Briefings
Quarterly Business Review
Policies & Compliance
Written down, and actually true.
We write and maintain the policies your regulators and customers expect, and map your controls to the frameworks that apply: NIST CSF, CIS Controls, Reg S-P, the FTC Safeguards Rule, PCI DSS and SOC 2 readiness.
A policy that says "MFA for all users" is a liability if one admin account does not have it. We check that the setting matches the paper.
Written Security Program
Framework Mapping
Evidence File
Annual Policy Review
Incident Readiness
Ready before the bad day.
We own the incident response plan, run tabletop exercises with leadership and set the escalation path, so everyone knows who calls the insurer, counsel and the bank.
The first hours of an incident decide most of its cost. A plan nobody has practiced is not a plan.
Incident Response Plan
Executive Tabletop Exercises
Escalation and Notification Paths
Backup Recovery Testing
Vendor & MSP Oversight
Independent of the people you oversee.
We hold your MSP, MSSP and software vendors to written standards, review their access and reports, and check that what they say is running is actually running.
Your MSP should not grade its own work. An independent security leader can tell you plainly what is working and what is not.
MSP and MSSP Oversight
Vendor Risk Reviews
Third-Party Access Reviews
Tool and License Rationalization
Insurance, Diligence & Customer Assurance
One person who can stand behind the answers.
We answer cyber insurance applications, LP and lender questionnaires, customer security reviews and diligence requests, with the evidence attached.
Every one of these answers is a statement your company can be held to. It should come from the person who owns the program.
Cyber Insurance Applications
LP and Lender Questionnaires
Customer Security Reviews
Deal Diligence Support
SOC 2 Readiness
Why Companies Choose a Fractional CISO
Senior security leadership when you need it, without a full-time executive hire.
Senior Leadership, Fractional Hours
A full-time CISO is a senior executive hire with salary, bonus, equity and a long search. A vCISO gives you the same accountability, scaled to the hours your company actually needs.
Independent of Your MSP
Your vCISO reports to leadership, not to the provider running your IT. That separation is what lets the program be measured honestly.
Board-Ready Every Quarter
Each quarter ends in a QBR: what changed, which risks went down, what is left and what it will take. Boards and sponsors get a report they can read in ten minutes.
One Owner for Outside Questions
Insurers, examiners, LPs and customers get consistent answers from the person who owns the program, backed by evidence instead of memory.
Two ways to work with your vCISO
Most companies start with Jumpstart CISO, a fixed-scope project, then decide whether to continue on retainer. Companies that already know what they need can start on retainer. Either way you get a written scope and fee before any work starts.
Jumpstart CISO
A fixed-scope engagement for a CIA triad uplift. We get in, audit, analyze, recommend and report back in your first quarterly business review. Best when you need a baseline and a plan fast: before an exam, a renewal, a board meeting or the first 100 days after a deal.
- Security baseline across confidentiality, integrity and availability
- Risk register scored by business impact
- Prioritized 12-month roadmap with budget ranges
- First QBR with leadership or the board
vCISO Retainer
Ongoing security leadership. Your vCISO owns the program, works the roadmap with your team and your providers, answers outside questions, and runs a QBR every quarter.
- A named security leader for your company
- Program, policy and vendor ownership
- Insurance, LP, customer and examiner questions
- A QBR every quarter, scored against the baseline
What the CIA triad means for your business
Confidentiality, integrity and availability are the standard way security leaders describe what they protect. Jumpstart CISO scores your program on each one, in business terms, so the board can see where risk sits.
Only the right people can see your data: client files, deal documents, financials and employee records. We check identity, MFA, admin access, file sharing and email.
Records, approvals and payments are what they should be, and nobody can quietly change bank details. We check payment-change controls, email security, logging and change approval.
The business keeps running when something breaks. We check backups, recovery testing, ransomware readiness and how long you could operate without key systems.
Jumpstart CISO:
From Audit to First QBR
Jumpstart CISO is a fixed-scope project for companies that need a security baseline and a plan before they commit to a retainer.
It measures your program against the CIA triad: confidentiality, integrity and availability.
At the end you can keep Cloudskope on retainer to execute the plan or take it in-house. Either way, you own the roadmap.
How Jumpstart CISO Works
Get in, audit, analyze, recommend, then report.
The first QBR sets the baseline every later quarter is measured against.
Get In
Kickoff with leadership, read-only access to your environment, and interviews with IT, finance and your MSP. We learn how the business makes money and what it cannot afford to lose.
Audit
We test the controls that matter: identity and MFA, email and Microsoft 365, endpoints, backups, vendors and payment approvals. Actual settings, not self-reported answers.
Analyze
Every finding is scored for confidentiality, integrity and availability, and for business impact. That becomes your risk register.
Recommend
A prioritized roadmap: what to fix this month, this quarter and this year, with owners, effort and budget ranges.
Retainer or In-House
You choose who executes the roadmap: keep your vCISO on retainer, hand it to your team, or mix the two.
The plan works either way.
Quarterly Business Review
Leadership and the board see the baseline, the CIA scorecard and the plan.
Every quarter after that is measured against it.
What a vCISO costs, and what drives it
vCISO pricing is usually a monthly retainer or a fixed project fee, not an hourly rate. We do not publish a price because the honest answer depends on the factors below. After a short call you get a written scope and fee.
Size and complexity. Users, locations, cloud tenants, and how many systems hold sensitive data.
Regulators and frameworks. SEC Reg S-P, the FTC Safeguards Rule, PCI DSS, HIPAA, SOC 2 or CMMC each add evidence work.
Where the program starts. Written policies and a working risk register take less effort to run than a program built from scratch.
Outside demands. Board meetings, LP reporting, insurance renewals, customer reviews and deals planned in the next 12 months.
Hands-on time. Whether your vCISO only leads, or also works directly with your IT team and providers on the fixes.
How to choose a vCISO
One named person. Ask who your vCISO will be, not which team handles requests.
Independence. Your vCISO should report to leadership, not to the provider running your IT.
Board-ready reporting. Ask to see a redacted sample of a quarterly report. If a director cannot read it in ten minutes, it will not get read.
Hands-on depth. Your vCISO should be able to read your Microsoft 365 and cloud settings, not only your policies.
A plan in weeks. You should have a baseline and a written roadmap within the first engagement, not after a long discovery phase.
Who leads your vCISO engagement
Your vCISO is Dipan Mann, Cloudskope's founder, CEO and CTO. He started in public-sector environments where risk was assessed with Department of State and DoD-grade discipline, then worked alongside venture and private equity firms evaluating technology companies and the risks that could derail them, and held operating roles at Kana Software, LiveVox and LogicMonitor. More about Cloudskope.
vCISO Questions, Answered
Straight answers on cost, scope, your MSP and what a quarterly review covers.
1What does a vCISO do?
A vCISO owns your security program: strategy, roadmap, risk register, policies, vendor oversight and incident readiness. They report on it to leadership and the board, and answer the security questions that come from examiners, insurers, LPs, lenders and customers.
2What is the difference between a vCISO and a fractional CISO?
In practice, very little. Both describe a senior security leader working part time for your company. "Fractional CISO" usually stresses a set share of one person's time; "vCISO" and "CISO as a service" are broader and sometimes mean a rotating team. Ask who your named leader will be.
3How much does a vCISO cost?
It depends on your size, your regulators, where your program starts and how much hands-on work you need. Most engagements are a monthly retainer or a fixed project fee, well below the cost of a full-time executive. We give you a written scope and fee after a short call.
4Do we need a vCISO if we already have an MSP?
Usually, yes. Your MSP runs your systems. A vCISO sets the standard those systems should meet, checks that they meet it, and reports the result to leadership. A provider should not grade its own work. Your vCISO works alongside your MSP, not against it.
5What is Jumpstart CISO?
A fixed-scope project for a CIA triad uplift. We get in, audit your controls, analyze the findings by business impact, recommend a prioritized roadmap and present it in your first quarterly business review. Afterward you can keep Cloudskope on retainer or take the plan in-house.
6What is in a vCISO quarterly business review?
What changed since last quarter, a scorecard across confidentiality, integrity and availability, the top risks, progress against the roadmap, and the decisions leadership needs to make. It is built for a board to read in about ten minutes.
7Can a vCISO help with SEC exams, cyber insurance and SOC 2?
Yes. Your vCISO keeps the evidence for Reg S-P and Reg S-ID, checks cyber insurance answers against your actual settings, and runs SOC 2 readiness. Our SEC exam checklist and cyber insurance application check are good places to start.
8Who will our vCISO be, and how fast can we start?
Your vCISO is Dipan Mann, Cloudskope's founder. Engagements usually start within weeks, much faster than a full-time executive search. The first step is a short call to scope the work.
Put One Person in Charge of Security
Book a strategy session to talk through your program, your next exam, renewal or deal, and whether a retainer or Jumpstart CISO fits.
You will speak with the person who would lead the work.