AI Skills — Compliance and Security
How a YC Startup Closed a $1.5M Deal With 5 Security Documents
Hyperbound, a YC-backed startup, ran the Vanta SOC 2 track and closed a $1.5M enterprise deal three months later. Not because their product got better in that window. Because they cleared the security review the enterprise required. This skill pack gives you the five documents that do the same job, plus a prompt to build your AI vendor audit in under an hour.
The Problem
Enterprise clients do not ask about your product first. They ask about your security posture.
Which tools touch their data? Where is that data stored? What happens if there is a breach? Do you comply with the AI Act or GDPR?
If you cannot answer those questions with documentation, you do not get to the next meeting. It does not matter how good your service is. Enterprise procurement runs on evidence, not conversations.
Most small businesses and agencies are already running AI tools in their operations: Claude or the OpenAI API for tasks, n8n or Zapier for automation, Notion for client work, Gmail for communication. Every one of those tools touches customer data in some form. Enterprise buyers know this. They will ask about it.
The businesses that have the documents in place close faster. The ones that say "we can get those to you next week" lose to whoever already has them.
Copy: AI Vendor Security Audit Prompt
This prompt generates your vendor audit: the most time-consuming compliance document to build from scratch, and the one that feeds directly into your data processing agreements and breach plan.
Start here. The other four documents in the skill pack follow from it.
Copy this.
I am building a security compliance document set for my business. I use AI tools and automation platforms in my operations. I need to document which tools touch customer data and what our compliance posture looks like for each. For each tool I list below, produce a security review row with these fields: - Tool name - Data types it processes (choose from: PII / financial records / business operations data / none) - Data storage location (US / EU / unknown / customer-controlled) - Relevant certifications this vendor holds (SOC 2 / ISO 27001 / GDPR-compliant / AI Act assessed / none listed) - Our data exposure level (high / medium / low — based on what data the tool can see and how it handles it) - Required action from us (e.g. sign a Data Processing Agreement / review their data retention policy / none needed) Format as a table. After the table, give me a priority list: which tool to address first based on exposure level, and what the single most important action is for each. My tools: [LIST YOUR TOOLS — e.g. Claude API, OpenAI API, n8n, Notion, Zapier, HubSpot, Google Workspace, Calendly, Stripe] I am a [BUSINESS TYPE: agency / SaaS startup / consulting firm / solo operator] serving [CLIENT TYPE: SMB / enterprise / healthcare / financial services].
How to Use It
Run this prompt in Claude or Codex. Replace the bracketed placeholders with your actual tools and business type. The output gives you the vendor audit table. Export it, format it in your company template, and keep it as a living document. Update it when you add a new tool.
What You Get Back
The full skill pack contains five documents. Here is what each one does:
01. AI Vendor Security Audit. The table from the prompt above. Maps every tool in your stack to the data it touches and the compliance status each vendor holds. This is the document enterprise buyers ask for first.
02. Data Processing Agreement Template. Pre-filled for the tools in your stack that require one. Covers data retention, deletion rights, breach notification, and subprocessor disclosure. Most enterprise procurement departments have their own DPA template; having yours ready signals that you take this seriously.
03. Breach Response Plan. A one-page procedure: who gets notified, in what order, within what timeframe. EU GDPR requires 72-hour notification to regulators. Having the plan written before an incident means you do not improvise during one.
04. AI Act Compliance Checklist. Covers the EU AI Act requirements for AI systems that interact with customers or make automated decisions. Relevant if you serve EU-based clients or plan to. Checks transparency obligations, prohibited practices, and documentation requirements.
05. One-Page Security Overview. A client-facing summary of your security posture in plain language. Non-technical. Covers data handling, access controls, vendor vetting, and incident response. This is what you send to a procurement team instead of a 40-page SOC 2 report.
Together, these five documents represent a security posture that clears most SMB and mid-market enterprise security reviews.
Honest Limits
This pack does not replace a full SOC 2 audit. If you are targeting Fortune 500 companies or regulated industries like healthcare, financial services, or government, you will need formal certification. Tools like Vanta automate the evidence collection for SOC 2 Type I and Type II. The Hyperbound case is that path: they used Vanta for the SOC 2 track and it took three months.
For most agencies and service businesses moving into enterprise, the five-document pack clears enough of the security review to get to the decision stage. Once you are closing enterprise deals consistently, then the investment in formal certification makes sense.
One specific note: the AI Act compliance checklist is based on the regulation as of mid-2026. The EU is still issuing implementation guidance for specific provisions. Review the checklist against the latest published guidance before handing it to EU-based procurement.
Most businesses running AI in their operations do not have any of these documents. That is the gap you close this week.
The next time a prospective enterprise client asks about your security posture, you send the one-pager before they finish the question. Run the vendor audit prompt now. It takes under an hour. The other four documents build from there.