Cyber Insurance Readiness Assessment

Know your gaps, gather the evidence, and prioritize what matters before renewal.

Two weeks. One prioritized plan.

BUILT FOR GROWING BUSINESSES

Insurers increasingly ask for proof that core safeguards are in place. Cyber Winter turns that questionnaire anxiety into a focused, business-friendly plan - without burying your team in jargon.

You leave with a decision-ready roadmap

We translate technical gaps into business priorities so leadership, IT, and your insurance broker can move forward with the same picture.

Pricing

Fixed-fee launch package: $2,500–$3,500

Up to 50 employees $2,500 · 51–100 employees $3,500

One business entity, standard technology environment. Remote delivery included.

Process

01 / DISCOVER: Kickoff + evidence

One focused session and a streamlined document request.

02 / ASSESS: Review + prioritize

Independent analysis through a business-risk lens.

03 / DECIDE: Scorecard + plan

Leadership debrief with clear ownership and sequencing.

What's included

• Readiness kickoff: goals, renewal timing, business context, and current controls.

• Focused control review: identity and access, phishing-resistant multifactor authentication, endpoint detection and response, email security, immutable and offline backups, patching, incident response, and security awareness.

• Evidence checklist: what you already have, what is missing, and who should own each item.

• Executive scorecard: a plain-language Red / Yellow / Green view of readiness.

• 90-day action plan: prioritized by business impact, urgency, and effort.

• Leadership debrief: a 60-minute working session to agree on next steps.

Best fit

• Renewal or application is 30-90 days away

• No dedicated security leader

• Leadership needs a practical plan

• IT is managed internally or by an MSP

Optional follow-through: Need a written security program? Our WISP Package turns your assessment findings into the written plan the FTC Safeguards Rule requires, at 15% off when booked within 90 days of your readout.

Readiness assessment only; not a penetration test, legal opinion, compliance certification, or guarantee of coverage or pricing.