Headcount Zero

Jordan
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Headcount Zero is about scaling a company with AI and no employees. Each week, Jordan breaks down one practical system to win customers, deliver better work, and protect margin.

Episodes

  1. Stop Chasing Invoices: Zero-Touch Dunning with Stripe Smart Retries

    2D AGO

    Stop Chasing Invoices: Zero-Touch Dunning with Stripe Smart Retries

    Solo operators lose thousands in recoverable revenue to failed payments they never chase. This episode shows you how to build a zero-touch dunning system using Stripe Smart Retries plus Make/Zapier webhooks that automatically recovers failed payments while you focus on delivery. Jordan walks through the exact Dashboard configuration (8 attempts over 2 weeks), webhook orchestration for customer emails and Slack alerts, Notion tracking, and Test Clock validation. Includes ACH Direct Debit handling, idempotency patterns, and the client proof dashboard that turns invisible automation into visible value. The complete system takes 90 minutes to build and runs forever—no manual follow-ups, no awkward conversations, just recovered revenue hitting your account automatically.

    26 min
  2. Zero-Touch Client Onboarding: E-Sign to Welcome Pack in 45 Minutes

    MAR 25

    Zero-Touch Client Onboarding: E-Sign to Welcome Pack in 45 Minutes

    Turn signed contracts into fully provisioned client workspaces in under an hour—completely automated. Jordan walks through the exact chain from PandaDoc webhook to Stripe payment processing to Notion workspace creation to Google Drive folder setup to welcome email delivery. You'll get the complete Make scenario with idempotency checks, error handlers, and rollback logic so nothing gets created twice and partial failures clean up automatically. Includes downloadable templates for the Notion Client Hub, Onboarding Runs database, Gmail welcome email, and the complete automation blueprint you can import directly into Make or Zapier.

    31 min
  3. Change Order Automation: Stop Scope Creep with Slack + Notion + PandaDoc + Stripe

    MAR 18

    Change Order Automation: Stop Scope Creep with Slack + Notion + PandaDoc + Stripe

    Solo operators lose thousands to scope creep through informal client requests. Jordan shows you how to build a complete automation that catches every "quick favor," classifies it as in or out of scope, generates a priced change order, and blocks work until both signature and payment clear. Using Slack for approvals, Notion for data, PandaDoc for documents, and Stripe for payment gates, this system protects your margins while you sleep. Includes templates for Notion databases, PandaDoc merge fields, Slack approval buttons, and both Zapier and Make blueprints.

    22 min
  4. Stop Taking Bad Discovery Calls: AI-Powered Lead Qualification That Guards Your Calendar

    MAR 11

    Stop Taking Bad Discovery Calls: AI-Powered Lead Qualification That Guards Your Calendar

    Jordan tracked 83 discovery calls over six months—47 were complete wastes of time. Budget mismatches, timeline disconnects, people wanting services he doesn't even offer. That's 35 hours of billable time lost to tire-kickers while qualified leads waited. So he built an AI-powered intake system that qualifies leads before they ever see his calendar. Qualified leads get instant booking links with pricing anchored. Non-fits get helpful redirects. Zero human touch until someone's actually worth talking to. His close rate jumped from 18% to 62%—not because he got better at selling, but because he stopped wasting time on people who were never going to buy. This episode shows you exactly how to build the same system using Zapier's new AI Guardrails or Make's If-else modules, with form sanitization, LLM qualification, and bulletproof routing that never leaks calendar links to unqualified prospects.

    20 min
  5. Ship a Zero-Touch Client Proof Digest (Gmail + Make + Notion) in 90 Minutes

    MAR 4

    Ship a Zero-Touch Client Proof Digest (Gmail + Make + Notion) in 90 Minutes

    Your best automation work is invisible—and that's killing your client relationships. When automations run perfectly in the background, clients forget they exist and start questioning what they're paying for. This episode shows you how to build a zero-touch weekly digest that makes your invisible work visible, using Gmail, Make.com, and Notion to automatically compile everything you shipped into a client-readable proof of value. No manual reporting, no weekly check-ins—just automated visibility that reduces churn and strengthens client relationships. Jordan walks through the complete build: Gmail v4 module setup with proper search operators, LLM summarization with hallucination safeguards, Notion client portal integration, and optional Slack/PDF outputs. Includes gotchas like Gmail reauthorization limits, Notion API rate limits, timezone handling, and cost optimization strategies. Plus alternatives for Zapier, n8n, and HubSpot users. Everything you need to ship this in 90 minutes and start preventing churn immediately.

    17 min
  • 5 Episodes

About

Headcount Zero is about scaling a company with AI and no employees. Each week, Jordan breaks down one practical system to win customers, deliver better work, and protect margin.

Information

  • Creator
    Jordan
  • Episodes
    5
  • Rating
    Clean
  • Copyright
    © 2026 Headcount Zero
  • Show Website
    Headcount Zero