EPISODE · May 5, 2026 · 18 MIN
Build a Trust Center That Wins Enterprise Deals
from Headcount Zero · host Jordan
Solo automation consultants pursuing enterprise clients face a hidden deal-killer: vendor security questionnaires. When procurement sends you 261 questions about your encryption policy, subprocessor list, and AI data handling, you need artifacts, not explanations. This episode builds the complete trust surface that prevents deals from dying in procurement — a one-page Notion Trust Center, a living subprocessor register, a plain-language Data Processing Addendum, and a Make scenario that automates DPA signature and storage. Jordan walks through the exact structure that mirrors CAIQ, SIG, and SOC 2 frameworks, includes the AI section buyers now expect, and provides copy-safe answers for the most common questionnaire prompts. Plus: the automation that turns DPA signing from a week-long email chain into a single status change in Notion.
What this episode covers
Solo automation consultants pursuing enterprise clients face a hidden deal-killer: vendor security questionnaires. When procurement sends you 261 questions about your encryption policy, subprocessor list, and AI data handling, you need artifacts, not explanations. This episode builds the complete trust surface that prevents deals from dying in procurement — a one-page Notion Trust Center, a living subprocessor register, a plain-language Data Processing Addendum, and a Make scenario that automates DPA signature and storage. Jordan walks through the exact structure that mirrors CAIQ, SIG, and SOC 2 frameworks, includes the AI section buyers now expect, and provides copy-safe answers for the most common questionnaire prompts. Plus: the automation that turns DPA signing from a week-long email chain into a single status change in Notion.
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Build a Trust Center That Wins Enterprise Deals
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