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Cyber Insurance Readiness Assessment for Small Businesses

For businesses that want to make sure their cyber insurance actually covers them.

What Is This?

A Cyber Insurance Readiness Assessment is a comprehensive review of your IT environment against what your cyber insurance carrier requires. I audit your security controls, backup procedures, access management, incident response planning, and documentation to identify gaps between what you told the carrier and what you actually have in place.

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The result is a clear report showing what controls are in place, what's missing, and what you need to fix to ensure your cyber insurance coverage actually applies when you need it.

Why You Need It

You bought cyber insurance thinking you were covered. But when you applied, you checked boxes that said you have MFA, encryption, tested backup, incident response planning, and documented access controls.

The problem: most small businesses don't actually have all of those things in place, or they have them partially configured. If you get hit with ransomware and file a claim, the carrier investigates. They ask for evidence that the controls you claimed to have were actually in place. If they weren't, they can deny your claim.

This assessment tells you the truth about what's actually in place versus what you told the carrier.

Who This Is For

Any small business that carries cyber insurance. Businesses preparing for cyber insurance renewal and unsure if their environment matches their application. Companies that have been denied a claim or had coverage reduced and want to understand why. Organizations in regulated industries (healthcare, financial services, law) that need specific controls their carrier requires. Businesses that have had a security incident and want to make sure their claim will actually be covered. Any company that wants to renew their policy with accurate, defensible information instead of guessing what controls they have.

What Happens When You Don't Match Your Application

  • Your claim gets denied. You file a ransomware claim expecting $500,000 in coverage. The carrier investigates and finds that you don't actually have MFA enforced like you said you did. They deny the claim based on misrepresentation.

  • Your coverage gets reduced at renewal. You renew your cyber insurance expecting similar coverage. The carrier asks for evidence of controls. You can't provide it. Your coverage gets reduced or premium goes up significantly.

  • Your incident response is chaos. You get breached and don't know what to do. You don't have a written incident response plan. You don't know the 60-day notification deadline. You don't know how to communicate with customers or regulators. The delay and confusion make the breach worse and more expensive.

  • Your backup doesn't work when you need it. Ransomware hits and you go to recover from backup. The backup process hasn't been tested in years. The restore fails. You're paying a ransom or losing critical data.

  • You can't produce evidence of controls. The carrier asks for documentation that MFA is enforced, that backups are tested, that access controls are in place. You don't have any of it documented. You look unprepared and the carrier questions whether you're being truthful.

  • HIPAA or FTC enforcement finds gaps. OCR or FTC investigators ask for your risk analysis, your security policies, your backup procedures. You don't have proper documentation. The gap becomes a violation with financial penalties.

  • You're paying for coverage you don't actually have. You're paying premiums for controls that don't exist. When something goes wrong, you discover the coverage doesn't apply.

What's Included

Security Controls Audit

  • MFA implementation and enforcement status

  • Endpoint protection and antivirus coverage

  • Email security and anti-phishing configuration

  • Firewall and network security

  • Device encryption and access controls

  • Patch management and software updates

Backup & Disaster Recovery Assessment

  • Backup procedures and frequency

  • Off-site backup and redundancy

  • Tested restore procedures and documentation

  • Recovery time and data loss estimates

  • Ransomware protection in backup strategy

Access Management Review

  • User account management and unique identifiers

  • Password policies and complexity

  • Remote access security and MFA

  • Shared account identification

  • Access revocation procedures

Compliance & Regulatory Requirements (if applicable)

  • HIPAA technical safeguards (healthcare)

  • FTC Safeguards compliance (financial services)

  • CMMC requirements (defense contractors)

  • Industry-specific regulatory obligations

Incident Response Planning

  • Written incident response plan (or lack thereof)

  • Breach notification procedures

  • Communication plan and templates

  • Escalation paths and decision-makers

  • Regulatory notification timelines

Documentation & Evidence

  • Risk analysis and risk assessment

  • Security policies and procedures

  • Training and awareness documentation

  • Audit logs and monitoring evidence

  • Vendor and Business Associate Agreements

Carrier Requirements Alignment

  • Coverage gaps based on your policy

  • Controls the carrier specifically requires

  • Documentation the carrier will ask for

  • Evidence package assembly

Prioritized Action Plan

  • What to fix before renewal

  • What to document immediately

  • Implementation timeline

  • Quick wins vs. long-term projects

What You Get

Written Assessment Report
Comprehensive documentation of your current controls against what your carrier requires.

Executive Summary
High-level overview of what's in place, what's missing, and what matters most for your coverage.

Control Inventory
Complete list of security controls, backup procedures, access management, and compliance documentation currently in place.

Gap Analysis
Specific gaps identified against your carrier's requirements with coverage impact.

Evidence Package
Documentation you can provide to your carrier showing controls are in place (or evidence of what needs to be implemented).

Renewal Questionnaire Walkthrough
Guidance on how to answer your cyber insurance renewal questionnaire accurately based on what's actually in place.

Prioritized Action Plan
Clear recommendations for what to implement or document before renewal, in priority order.

Consultation Call
30-minute call to walk through the assessment, answer questions, and discuss implementation options.

Timeline

Assessment typically takes 2-3 weeks. I'll audit your controls, review your policies, document what's in place, and compile the report with the evidence package. You get the written assessment and a 30-minute consultation call to review findings.

Pricing

$1,750 flat

No hourly billing. Fixed price regardless of environment size or complexity.

What Happens After

You get the assessment report and evidence package. You can:

  1. Use it to implement missing controls before renewal

  2. Use it to fill out your renewal questionnaire accurately

  3. Use it to justify premium or coverage decisions

  4. Share it with your insurance broker for discussion

  5. Use it as the foundation for hiring IT support to fix gaps

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This assessment stands on its own. It's yours to use however you want.

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Frequently Asked Questions

Will this assessment hurt my insurance renewal?

No. This assessment is for you. It identifies what's actually in place so you can answer your renewal questionnaire accurately. Inaccurate questionnaires are what hurt renewals. Accurate questionnaires with evidence of controls are what carriers want to see.

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What if the assessment finds controls are missing?

Then you know before renewal. You can either implement the controls, or you can answer the renewal questionnaire accurately about what's not in place. Either way, you're protected from claim denial due to misrepresentation.

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Can my insurance broker use this assessment?

Yes. Many businesses share this assessment with their broker to help with renewal conversations. The broker can use it to justify coverage options or discuss premium changes with you.

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How long do we have to implement missing controls before renewal?

That depends on your renewal date and what's missing. Some controls are quick to implement (MFA enforcement, email security settings). Others take longer (incident response planning, documentation). I'll prioritize what matters most and give you a timeline based on your renewal date.

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What if my carrier requires something specific?

The assessment reviews against general cyber insurance requirements. If your carrier has specific requirements beyond standard coverage, bring those to the consultation call and I can address them specifically.

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Do I have to implement everything before renewal?

No. But you should accurately report on your renewal questionnaire what controls are in place and what aren't. Carriers want accuracy. Missing controls with honest disclosure is better than missing controls with misrepresentation.

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Will this assessment cover compliance requirements for my industry?

Yes. If you're in healthcare (HIPAA), financial services (FTC Safeguards), or defense contracting (CMMC), I'll review your controls against those requirements as well as cyber insurance requirements.

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What if we get hit with ransomware before we implement recommendations?

That's the risk. This assessment helps you understand that risk and make decisions about what to fix first. Some controls reduce ransomware risk directly (backup, endpoint protection). Those are usually the top priority.

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Can you implement the recommendations for us?

Yes. I can do that as a separate engagement. The assessment findings become the foundation for implementation work, either as a standalone project or as part of an ongoing managed IT relationship.

 

How often should we do this assessment?

Before every cyber insurance renewal at minimum. Annual assessments are good practice, especially if you're implementing changes. If you're a managed IT client with me, we keep your controls current so you're always renewal-ready.

Ready to make sure your cyber insurance actually covers you?

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