Recommendation
Use Zapier to trigger on HubSpot contact changes, send a stable token payload to an AI copy service (Jasper if you have that Zap, or OpenAI/ChatGPT via Zapier’s OpenAI action/webhook), store template text and version metadata in an Airtable/Google Sheet, then create a scheduled send in HubSpot (or queue drafts) rather than sending immediately. This gives reliable tokens, an audit trail, and predictable scheduling.

Why this pattern
Separating: (1) contact trigger and token mapping, (2) AI generation, (3) draft creation/versioning, (4) scheduling — reduces flakiness and makes template/versioning auditable. Zapier handles integrations; the AI step can be Jasper or ChatGPT depending on your stack and budget.

Decision criteria (pick based on your team and constraints)
- Budget & skill: Use Zapier’s built-in OpenAI action or a Jasper Zap for low/no-dev setup. If you need custom prompts/APIs or higher throughput, use webhooks and a developer to call Jasper/OpenAI APIs.
- Team size & audit needs: Airtable/Google Sheets for small teams; database or Git-backed templates for enterprise audit trails.
- Workflow stage & output quality: If drafts must be reviewed, generate drafts and set HubSpot owners/tasks. If fully automated, include strict QA checks and opt-out safeguards.

Step-by-step Zap (practical)
1) Trigger: HubSpot — New or Updated Contact (filter on property like “Ready for email” or lifecycle stage). Use a custom property to gate automation.
2) Formatter/Code: Build a token map (JSON) from HubSpot fields you’ll rely on: first_name, company, deal_size, last_activity_date, buyer_segment. Keep token keys fixed; make a mapping table in your sheet so Zapier always uses the same token names.
3) Lookup template + version: Use Airtable/Sheets lookup (by template ID) that returns prompt wrapper and version number. This is your canonical template repo. Save template_id + version to Zap logs.
4) AI generation: Call Jasper (via Zapier Jasper action or webhook) or ChatGPT/OpenAI. Send the wrapper prompt + token map. Include an explicit “template_id: X, version: Y” line in the prompt so output records the source. Use temperature=0.2–0.4 for consistent, on-brand copy.
5) Post-process: Use Formatter to replace token placeholders and run a quick profanity/email-safety check (simple regex/blacklist). Store the generated copy + template_id + version into Airtable/Sheets for audit.
6) Create draft in HubSpot: Create Email or Create Engagement (note: HubSpot Marketing Email API may be required to truly schedule marketing sends). Alternatively create a CRM task for reviewer + HubSpot scheduled send action.
7) Schedule: Use Zapier’s Delay Until (or HubSpot scheduling action) to set the send time. If timezone matters, convert times robustly.
8) Logging & error handling: On failure, route to Slack or email and set status in your template sheet.

Practical checklist
- Lock token names in a mapping table before building zaps
- Keep template text + version in Airtable/Sheets and reference by ID
- Include template_id & version in the AI prompt and save AI output with those fields
- Use low temperature for consistent outputs
- Have a manual QA path (task or review step) for high-risk sends
- Add unsubscribe/compliance checks and logging

Best-for / Avoid-if
Best for: scalable personalized sequences, sales follow-ups, nurture emails where speed and personalization matter.
Avoid if: messages are legally sensitive, require strict regulatory records beyond simple audit logs, or must come from strictly human-written copy.

If you want, I can sketch the exact prompt format to send to Jasper/OpenAI and a sample Airtable schema. CTA: If you plan to build this in Zapier I recommend starting with Zapier’s HubSpot and AI actions for the fastest proof-of-concept.

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