First Steps to Buying Cybersecurity Insurance: Checklist for New Buyers

Content Pillar: Cybersecurity Insurance Basics
Audience: U.S.–based business owners, CFOs, CISOs, risk managers
Word Count: ≈ 2,800

Table of Contents

  1. Why Cybersecurity Insurance Is No Longer Optional
  2. Current U.S. Market Snapshot & Premium Benchmarks
  3. Ultimate 12-Point Checklist for First-Time Buyers
  4. Cost Comparison of Leading U.S. Insurers
  5. Location-Specific Underwriting Hotspots
  6. Frequently Asked Questions
  7. Key Takeaways

Why Cybersecurity Insurance Is No Longer Optional

Ransomware demands in the United States soared 518 % between 2020 and 2022 (Source: SonicWall Cyber Threat Report, 2023). The average total cost of a data breach for U.S. organizations hit $9.44 million in 2022 (Source: IBM Cost of a Data Breach Report, 2023).

With stakes that high, cybersecurity insurance has evolved from “nice-to-have” to board-level mandate. If you’re still shopping for your first policy, you are already late to the party—yet you can still negotiate strong coverage if you know the right first steps.

For a plain-English primer on fundamentals, bookmark Cybersecurity Insurance 101: What It Is and Why Your Business Can’t Ignore It.

Current U.S. Market Snapshot & Premium Benchmarks

Metric 2021 2022 2023 (est.)
Total U.S. market size (gross written premium) $4.8 B $6.5 B $8.2 B
Median annual premium for SMBs (<250 employees) $1,100 $1,450 $1,590
Median retention/deductible (per incident) $10,000 $15,000 $25,000
Average ransomware sub-limit included $500,000 $250,000 $100,000

Source: Marsh Global Insurance Market Index, Q4 2023; NAIC Cybersecurity Supplement filings.

Key trends:

  • Hardening market: Double-digit premium increases continued for the sixth straight quarter.
  • Higher deductibles: Insurers push more skin in the game back to the insured.
  • Coverage carve-outs: Some carriers exclude “nation-state” attacks or war exclusions—read the fine print.

For a deeper dive into policy mechanics, see How Cybersecurity Insurance Works: From Policy Purchase to Payout.

Ultimate 12-Point Checklist for First-Time Buyers

Below is a structured, expert-vetted roadmap. Follow each step in order to maximize coverage, minimize cost, and satisfy underwriters on your first application.

1. Map Your Digital Footprint

  • Inventory all data assets (on-prem, cloud, SaaS).
  • Quantify record counts—especially PII, PHI, and PCI data.
  • Identify third-party vendors and API dependencies.

2. Calculate Your Maximum Probable Loss (MPL)

Before you can decide on policy limits, you need a financial model:

  • Multiply average incident cost by likelihood (use historical or industry benchmarks).
  • Include intangible costs—brand damage, customer churn, legal defense.
  • Tools: FAIR methodology or simple Monte Carlo in Excel.

3. Benchmark Your Cyber Hygiene

Most U.S. insurers require baseline controls:

  • MFA on all privileged accounts
  • EDR solution deployed organization-wide
  • Secure, encrypted backups that are isolated/offline
  • Documented incident response plan and at least one table-top exercise

If you can’t confidently tick all of those boxes, expect a 15–40 % surcharge or even declination.

4. Decide on First-Party vs. Third-Party Coverage

First-party = your own costs (forensics, business interruption).
Third-party = liabilities to customers or partners (regulatory fines, class actions).
Most buyers need a blended policy, but confirm sub-limits are aligned with MPL.

5. Confirm Specialty Endorsements

Consider adding:

  • Social engineering / funds transfer fraud (FTF)
  • System failure (non-malicious downtime)
  • Bricking coverage (hardware replacement)
  • Media liability for content-driven businesses

6. Gather Underwriting Documentation

Insurers will ask for:

  1. Completed cyber application (carrier-specific)
  2. Latest penetration test summary
  3. SOC 2 or ISO 27001 certificates (if available)
  4. Recent backup logs & RPO/RTO metrics
  5. Board-approved cybersecurity policy

7. Work With a Specialist Broker

General commercial brokers may lack cyber expertise. Look for:

  • Brokers with CISSP, CISM, or CRISC credentials
  • Access to at least 10+ cyber-specific carriers
  • Ability to provide coverage comparisons, not just quotes

8. Solicit Multiple Quotes & Mock Endorsements

Request a sample policy form and endorsement schedule from each carrier. Line-by-line comparison reveals hidden exclusions.

9. Scrutinize Exclusions & Sublimits

Red-flag wording:

  • “Acts of war” or “nation-state actors”
  • “Failure to patch known vulnerability”
  • “Unauthorized collection of biometric data”

Ask for carve-backs or buy-backs where possible.

10. Negotiate Retroactive Date & Waiting Periods

  • Push the retro date back 6–12 months to capture dormant breaches.
  • Reduce business interruption waiting periods from 24 hours to 8–12 hours.

11. Align Incident Response Vendors

Most carriers provide a pre-approved panel (legal, forensics, PR). Get written permission for your preferred vendors if you want to keep existing relationships.

12. Build a Renewal Calendar

  • Start the renewal process 90 days prior to expiry.
  • Track claims, near-misses, and security upgrades for next year’s application.

For a jargon buster, check Beginners’ Guide to Cybersecurity Insurance Terminology and Concepts.

Cost Comparison of Leading U.S. Insurers

The table below reflects public filings, broker data, and 2023 sample quotes for a hypothetical 100-employee technology firm headquartered in Austin, TX with $20 M annual revenue and strong security controls.

Insurer Annual Premium Policy Limit Retention Notable Inclusions Source
Hiscox USA $9,800 $2 M aggregate $25k Social engineering ($250k), Business Interruption ($2M) Hiscox CyberClear Fact Sheet
Chubb $11,200 $2 M $25k Bricking, System Failure, Global coverage Chubb Cyber Index
Travelers $8,950 $1 M $15k Broad PCI coverage, Phishing training credit Travelers CyberRisk Product Overview
Cowbell Cyber $7,600 $1 M $10k Continuous risk scoring, Free ransomware coaching Cowbell Insights Report, 2023
AIG $12,400 $3 M $50k Higher limits, Extensive breach panel AIG CyberEdge Brochure

Note: Premiums vary ±25 % based on state, revenue, and security posture. Always obtain a custom quotation.

Location-Specific Underwriting Hotspots

Underwriters assign different risk weights by state because of regulatory differences, litigation climates, and incident frequency.

1. California

  • Cal. Civ. Code § 1798.82 imposes strict data-breach notification rules.
  • Litigation friendly; class-action suits common.
  • Expect premiums 15–20 % higher than national median.

2. New York

  • NYDFS Cybersecurity Regulation (23 NYCRR 500) adds compliance exposure.
  • Financial services concentration raises systemic risk.
  • Deductibles often start at $50,000 for mid-market firms.

3. Texas

  • Rapid tech growth in Austin, Dallas, Houston.
  • No additional state cyber mandates, so premiums slightly below average.
  • Ransomware incident frequency still high: 38 reported events in 2023 per Texas DIR.

4. Florida

  • Hurricane-driven property losses increase overall insurer portfolio risk, indirectly affecting cyber.
  • Older legal climate produced “assignment of benefits” abuse—carriers cautious.
  • Premiums roughly 5 % above national mean.

5. Illinois

  • BIPA (Biometric Information Privacy Act) fines up to $1,000 per negligent violation.
  • Many carriers now sub-limit biometric claims to $250k.

Real-World Scenario: A Startup Saved by Cyber Cover

In April 2023, a 30-person fintech startup in Chicago, IL suffered a ransomware attack that locked AWS instances. The firm’s Cowbell Cyber policy included:

  • $1 M ransomware sub-limit
  • $50k ransom payment coverage
  • $10k retention

Total incident costs reached $310,000 (forensics, downtime, PR). The insurer paid $300,000, keeping the company solvent. Read more in Can Cybersecurity Insurance Save Your Startup After a Breach? Foundational Facts.

Frequently Asked Questions

Q1. How much coverage do I really need?
A: Rule of thumb: Purchase limits equal to 2–3× your estimated Maximum Probable Loss. SMBs often choose $1–3 M; mid-market firms may need $5–10 M.

Q2. Will a previous breach make me uninsurable?
A: Not necessarily. Provide evidence of remediation steps (patches, MFA rollout) and you can still obtain coverage—albeit with a surcharge.

Q3. What’s the typical application turnaround?
A: For well-prepared applicants, brokers can secure quotes in 7–10 business days. Complex enterprises may take 30+ days.

Q4. Is cyber insurance tax-deductible?
A: Yes. Premiums are typically deductible as an ordinary and necessary business expense under IRS § 162.

Key Takeaways

  1. Start early. Give yourself at least 60–90 days before you need coverage to complete controls and paperwork.
  2. Quantify risk, then buy limits. Don’t guess. Use data-driven MPL calculations.
  3. Shop around. Premiums can differ by 40 % for identical limits in the same state.
  4. Negotiate exclusions. Ask for carve-backs on nation-state and software supply-chain events.
  5. Treat the policy as a living document. Update the insurer whenever you launch new products or expand internationally.

For expanded context, explore:

Need personalized guidance? Reach out to a licensed cyber-insurance broker or legal counsel to tailor the above checklist to your unique business model and state regulations.

Recommended Articles