Know what your cyber insurer will ask for, and have the proof ready.

We check your Microsoft 365, endpoint protection and backups against what underwriters require, then hand you a fix list, draft questionnaire answers and an evidence pack you can submit with confidence.

Fixed prices from $395 CAD. Read-only access. Based in Vancouver, serving the US and Canada.

Backups restore-tested Ready EDR on 18 of 18 devices Ready MFA: 2 exceptions Review DMARC at quarantine Review Evidence pack Questionnaire draft included
Sample snapshot for a fictional client. Your results depend on your systems.

Underwriters ask about controls. Your systems hold the proof.

Insurers now expect evidence, not a ticked box. Partial MFA is the most common reason small businesses fail an assessment, and a wrong answer can put a claim at risk later. We connect each question to what your systems actually show.

The question on the form

Is multi-factor authentication required for all remote access and email?

What we check and hand over

  • Conditional Access policy enforcing MFA for all usersReady
  • 3 accounts excluded from the policyReview
  • Every admin account has MFA registeredReady
  • Legacy sign-in, which bypasses MFA, still allowedGap

How an assessment works

  1. Connect read-only

    You approve a read-only app in Microsoft 365 and share your EDR and backup reports. Nothing in your tenant is changed, and you can revoke access in one click.

  2. Get your report

    Within 5 business days: a pass/review report by control, a prioritized fix list, and draft answers to your insurer's questions.

  3. Fix, then submit

    Close the gaps with your IT team, then get a final evidence pack, with every file fingerprinted so an underwriter can see it hasn't been altered.

Fixed prices, agreed before we start

Small-business cyber policies often cost $45 to $200 a month. Losing it can cost far more in client contracts.

Readiness check

$395 CAD, one-time

A quick read on where you stand, ideal if your renewal is a few months away.

  • Read-only scan of Microsoft 365
  • Readiness report with a pass/review status for each control
  • 30-minute call to walk through the results
Book a check

Readiness assessment

$895 CAD, one-time

Everything you need to answer your insurer with confidence. Up to 100 staff on Microsoft 365; larger setups are quoted after a short call.

Founding clients: the first 10 assessments are $495 in exchange for honest feedback and, if you're happy, a short testimonial.
  • Everything in the readiness check
  • Review of your endpoint, backup, incident plan and training evidence
  • Prioritized fix list your IT team can work through
  • Draft questionnaire answers linked to evidence
  • Re-check after fixes, and a final evidence pack for your underwriter
Book an assessment

Self-serve scan

$99 CAD, one-time

Sign up, connect Microsoft 365 and run the scan yourself. Good for checking where you stand before you talk to your broker.

  • 30 days of on-demand scans
  • Report, questionnaire draft and evidence pack
  • Upgrade to a full assessment any time
Sign up

Can someone send email as your company?

Insurers increasingly ask about SPF, DKIM and DMARC because spoofed email is how most invoice fraud starts. Enter your domain to check its public records. It takes a few seconds and needs no access to your systems.

The check runs in your browser using Cloudflare's public DNS. We don't see or store the domain you enter.

For IT providers: renewal season, without the scramble

Stop rebuilding the same insurance evidence for every client. Proofwell standardizes the assessment, prepares the report, and identifies the remediation work, saving you time across your entire customer base and turning the gaps into billable projects.

What you get for each client

  • One standard assessment: the same checks and scoring for every client
  • An insurer-ready report, questionnaire draft and evidence pack
  • A prioritized remediation list, ready to quote as project work
  • Read-only access, and your clients stay your clients
Become a founding partner

Founding partners

We'll assess two or three of your clients at no cost, so you can judge the reports before committing.

Founding partners get preferred per-tenant pricing and shape what we build next: a cross-client dashboard, scheduled re-scans, and reports under your own brand.

Who's behind Proofwell

Proofwell is run by Bryan Ward, a Vancouver-based security practitioner with nearly 30 years in IT and security. He ran IT operations and security at Softchoice, where he built the company's cyber security plan and managed infrastructure across 32 offices. Since 2018 he has worked in zero-trust security at Illumio, Guardicore and Akamai, where he served as a Field CISO.

Cyber insurers no longer accept a ticked box. They want proof of MFA, endpoint protection and tested backups, and a wrong answer can put a claim at risk. Bryan started Proofwell so small businesses can see exactly where they stand before the questionnaire arrives, and answer it honestly. His background covers what underwriters check: Microsoft infrastructure and identity, workload and network security, and backup and recovery.

Bryan on LinkedIn

Book an assessment

Tell us about your business and your renewal. We'll reply within one business day with a fixed quote and a time for a 20-minute call.

Prefer email? Write to [email protected].

Questions

Do you need access to our systems?

Read-only access to Microsoft 365 through an app you approve, plus exports from your endpoint protection and backup tools. We can't change anything, and you can remove the app at any time from your Microsoft 365 admin center.

What happens to our data?

We collect only what's needed to evidence each control, share it only with you and anyone you name (such as your broker), and delete working copies when the engagement ends unless you ask us to keep them for monitoring.

Does a readiness report guarantee coverage?

No. Insurers make their own decisions, and requirements differ by carrier and change over time. We help you find gaps and organize honest, evidence-backed answers. You review every answer before it goes to an underwriter.

We use Google Workspace, not Microsoft 365.

Get in touch. Endpoint, backup and email checks apply to any setup, and we can quote a manual review for Google Workspace.

Our IT provider handles security. Why would we need this?

Many good providers don't produce insurer-ready evidence by default. We work alongside them, and the fix list goes straight to the people who can act on it.