I’m building a focused service that helps B2B SaaS companies understand why enterprise security reviews get stuck. I’m looking for a contract CMMC/ SaaS Security Questionnaire Reviewer who can review customer security questionnaire responses through the lens of an enterprise CISO, auditor, or vendor-risk reviewer.
The goal is not simply to edit answers. The goal is to identify which answers are likely to stall a security review, trigger buyer follow-up, or block a deal because they are vague, unsupported, overbroad, contradictory, or not backed by evidence. This is not implementation work, legal review, audit certification, or a full vCISO engagement.
This is a bounded review role focused on identifying likely blockers and providing practical response direction.
What You’ll Review
A typical review packet may include:
Customer security questionnaire with current answers
Buyer / CISO / procurement follow-up comments
Client concern notes
SOC 2 or GRC status summary
Trust or security overview
Key evidence references, such as pen test summary, subprocessor list, policies, GRC exports, or trust center materials
What You’ll Do
Review questionnaire responses the way an enterprise CISO, auditor, or vendor-risk team would review them
Identify answers likely to trigger follow-up, concern, or rejection
Identify the questions most likely to stall a deal or require CTO, legal, security, or product escalation
Distinguish harmless wording issues from real security or evidence gaps
Flag claims that are not supported by SOC 2, policy, GRC evidence, or other proof
Identify vague, risky, overbroad, contradictory, or generic answers
Provide concise response direction that helps the client answer more defensibly without overclaiming
Identify what evidence would likely support a stronger answer
Identify when something cannot be fixed with wording and needs actual remediation or internal decision-making
What You Will Produce---
For each assessment, I may ask you to identify the top likely blockers and provide concise guidance, including:
Why the item may matter to the buyer
Whether the issue is a weak answer, missing evidence, risky claim, unclear owner, customer/legal requirement, or real security gap
What evidence would support the answer
What response direction makes sense
Who should own or escalate the item internally
What the client should avoid saying
You are not expected to complete the entire questionnaire, validate the full environment, provide legal advice, or join customer calls by default.
Skills Needed---
Experience with SaaS security questionnaires, customer trust, vendor risk, SOC 2, GRC, or enterprise security reviews
Ability to think like a buyer-side CISO, auditor, or vendor-risk reviewer
Experience identifying what stalls or blocks enterprise security reviews
Ability to review whether questionnaire answers are evidence-backed and defensible
Ability to distinguish weak wording from actual security gaps
Clear, concise writing
Practical judgment
Strong scope discipline
Useful Background
Experience with any of the following is helpful:
CMMC
SOC 2
ISO 27001
SIG / SIG Lite
CAIQ
Vendor risk reviews
Customer assurance / customer trust
Vanta, Drata, Secureframe, Sprinto, OneTrust, Conveyor, or similar tools
Security questionnaires for B2B SaaS companies
Enterprise procurement or security review workflows
Common Areas You May Review---
SOC 2 / compliance posture
Encryption and key management
MFA / SSO / access control
AI or customer data use
Data retention and deletion
Incident response
Breach notification
Vulnerability management
Penetration testing
BCP / disaster recovery
Subprocessors and vendor management
Logging and monitoring
Data residency
Security addendum or customer security commitments
This Is Not a Fit If
You want to audit the full company environment
You need to review every system/control before giving limited response direction
You want to perform remediation or implementation
You are looking for a full vCISO engagement
You over-engineer every answer
You are uncomfortable working from client-provided materials and giving bounded guidance
You want to complete questionnaires line by line as the main service
You cannot separate “bad answer” from “real security gap”
Engagement---
This is contract work. I’m starting with test packets to evaluate fit.
The test will involve a sample security questionnaire and supporting materials. I’ll ask you to identify the top likely blockers and track how long it takes.
If the fit is strong, work may be project-based as assessments are sold.
To Apply-Please include:
Relevant experience with SaaS security questionnaires, SOC 2, GRC, customer trust, vendor risk, auditing, or enterprise security reviews.
Any experience with Vanta, Drata, Secureframe, Sprinto, OneTrust, SIG, CAIQ, ISO 27001, CMMC, HIPAA, fintech, healthcare, or AI SaaS.
A short answer to this scenario:
A 70-person B2B SaaS company submitted a security questionnaire for a $150k enterprise deal. Many answers were generated from a GRC tool or prior questionnaire. The buyer’s security team has not rejected them outright, but the review is stalled. What answer patterns would you look for to identify the questions most likely causing concern, and how would you decide what the top blockers are?
A short answer to this second scenario:
A SaaS company answered, “Yes, all customer data is encrypted.” Why might that still concern an enterprise buyer, and what would you want to clarify before sending an updated response?