AI-powered cybersecurity guidance delivered by a real CISSP

Cyber insurance renewals shouldn’t keep your leadership team awake at night.

ClearPath helps nonprofits and small organizations complete security questionnaires, identify control gaps, and prepare for renewals—without hiring a full-time security leader.

Get your free readiness review → Try the Questionnaire Coach
Foot-in-the-door offer

Cyber Insurance Questionnaire Accelerator

$995 fixed fee
  • AI-assisted questionnaire completion
  • 90-minute working session
  • Gap analysis and control review
  • Executive summary
  • Prioritized next steps
A lower-risk way to experience ClearPath before a larger engagement.
✓ Fixed-fee entry offer
✓ CISSP + CISM judgment
✓ Plain language, no jargon
✓ Built for nonprofits and small orgs
Meet the Clear Path Questionnaire Coach

Turn intimidating questionnaires into plain-English next steps.

Upload your cyber insurance application or vendor security questionnaire and get a guided review that helps you understand what the question means, what evidence may be needed, and where your gaps are.

Try it free →
Upload cyber insurance application or vendor questionnaire

Receive guidance on:

Plain-English guidance
Suggested answers
Missing controls
Risk explanations
Recommended next steps
What we offer

Start small. Build trust. Fix what matters.

Scoped, practical services for organizations that need security leadership without a full-time hire.

Start here
⚡

Questionnaire Accelerator

Fixed fee · $995

A 90-minute working session to complete your questionnaire, identify gaps, and leave with next steps.

Learn more →
🔍

Technology Risk Baseline

One-time · $5,000–$8,500

A clear view of where risk is hiding, what matters most, and what to fix first.

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🛡

Insurance Readiness

Project · $6,000–$10,000

Support for renewal prep, control evidence, and readiness before underwriters ask.

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📋

Ongoing Risk Oversight

Monthly · $1,500–$2,500/mo

Lightweight monthly oversight to keep controls from drifting and surprises from showing up.

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Experience and judgment behind every engagement.

You get the speed of AI and the judgment of an experienced security executive.

CISSPCISMSecurity Executive

ClearPath brings hands-on leadership experience across cybersecurity and technology risk programs for large, mission-driven organizations.

Experience includes enterprise governance, cyber insurance readiness, vendor risk, board reporting, and practical technology risk oversight for mission-driven organizations.

Free resources

Get something useful before you ever book a call.

Use these as lead magnets for prospects who are not ready to buy yet.

Cyber Insurance Readiness Checklist

A practical prep list before renewal season.

Read the guide →

Board Cyber Risk Scorecard

A simple way to explain risk to non-technical leaders.

Browse resources →

Questionnaire Survival Guide

Plain-English help for answering insurer and vendor questions.

Read the guide →

Top 25 Insurer Questions

Common questions organizations should be ready to answer in 2026.

Browse resources →

Get your free Cyber Insurance Readiness Review.

Send over where you are in the renewal or questionnaire process. We’ll help you identify the next best step.

Get your free readiness review →