Headcount Zero podcast artwork

PODCAST · business

Headcount Zero

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.

  1. 33

    Stop Writing Custom Proposals: Build a 3-Tier Portfolio That Prices in Minutes

    Solo automation consultants waste hours writing custom proposals for projects that follow the same patterns. Jordan breaks down the 3-2-1 portfolio framework: three service tiers (Starter, Pro, Enterprise), two standardized add-ons, and one hard scope gate that lets you price any project in sixty seconds. Using real boundary language from nine automation shops, you'll learn to constrain workflows, channels, interactions, and support windows to make delivery predictable and margins sustainable. Includes the exact Notion Offer Catalog template with toggleable SLAs, red-and-yellow scope flags, and service card generator.

  2. 32

    The Enterprise Solo Pack: Trust Center + SSO + SLA Tiers That Close Deals

    Jordan breaks down how to package your security posture, questionnaire automation, and SSO capabilities into a named, priceable Enterprise Solo Pack that gets procurement teams to yes faster than larger agencies. Learn to build a Trust Center backed by CAIQ-Lite answers, price SSO as a scoped add-on, structure SLA tiers, and run the 10-minute demo that closes enterprise deals without anyone asking about your team size.

  3. 31

    Stop Flying Blind: Monitor Webhooks and Portals with Passive ZAP Scans

    Solo operators expose dozens of public endpoints—webhooks, client portals, form handlers—but unlike companies with security teams, nobody's checking if they're properly configured. This episode walks through setting up OWASP ZAP's passive baseline scan in Docker, scheduled weekly with cron, to catch missing security headers, CORS misconfigurations, and cookie issues before they cost you a client or a deal. Jordan covers the exact Docker Compose setup, config file tuning with OUTOFSCOPE patterns, exit code automation for Slack alerts, and ticket creation in Linear or Jira. The scan is passive-only and production-safe, designed as a regression safety net that catches configuration drift between deployments. Includes guidance on authenticated scanning with ZAP contexts, the critical endpoint inventory every solo needs, and honest limits about what passive scans can and can't catch.

  4. 30

    Build Your SLA Monitoring Loop: From Alert to Credit in One Afternoon

    Every proposal Jordan sends includes an SLA section promising 99.9% uptime and 20-minute update cadences. But for eight months, he had no way to prove it. This episode builds the complete SLA monitoring automation: your monitor fires, a draft status update appears for approval, Slack enforces update cadence, and credit calculations run automatically when incidents close. Learn to connect Statuspage's API to your monitoring stack, implement human-in-the-loop approval gates, and automate the credit math that turns incidents into trust signals. By the end, you'll have the infrastructure to operate SLAs instead of just promising them.

  5. 29

    Automate SLA Credits and Incident Comms From Your Audit Logs

    If you have SLA commitments in your contracts and you're still calculating credits manually — or worse, waiting for a client to ask before you even check — you are one bad month away from a trust conversation you can't win. This episode shows you how to automate the entire trust paperwork stack: credit math, ledger tracking, status page updates, and incident communications. Jordan walks through building an SLA automation pipeline that computes monthly uptime from your audit logs, applies vendor-grade credit ladders (like Twilio's 10% threshold and AWS S3's tiered system), writes monthly ledger entries automatically, and drafts incident updates via status page APIs before your client even knows something's wrong. You'll get the exact Make/n8n scenarios, Notion ledger schema, and templated incident communications that turn SLA management from a monthly spreadsheet nightmare into a set-and-forget system.

  6. 28

    Zero-Downtime Zapier Migration: 14-Day Shadow-Run + 15-Minute Cutover

    Jordan walks through the exact migration playbook he used to move a revenue-critical 12-step Zapier workflow to Make without losing a single lead. Learn the 14-day shadow-run methodology with correlation IDs and parity checks, the three Gate Zero checks that determine migration feasibility, and the 15-minute cutover process with a tested 60-second rollback. Includes current 2026 cost models comparing Zapier tasks vs Make credits vs n8n executions, SSO parity requirements across platforms, and webhook throughput limits. Jordan saved $400/month on this specific workflow while proving the new system matched the old one event-for-event before switching over.

  7. 27

    Stop Building Agents by Default

    Jordan challenges the default assumption that agents are the sophisticated choice for automation workflows. Using side-by-side testing data, he demonstrates that deterministic flows outperform agents on reliability and cost for 80% of production work. For the 20% where agents are justified, he shows exactly how to box them with tool allowlists, hard timeouts, per-run budgets, checkpoints, and approval gates. The episode includes a practical A/B testing harness to benchmark any agent against your deterministic baseline before going live, plus the framework updates from Microsoft Agent Framework and LangGraph that make strict guardrails possible.

  8. 26

    Build a Trust Center That Turns Security Questionnaires Into 40-Minute Tasks

    After losing a $14K/month deal because he couldn't answer a 48-page security questionnaire, Jordan built a system that turns vendor security reviews from deal-killers into 40-minute tasks. In this episode, he walks through building a public Trust Center in Notion, creating a reusable answer library mapped to CAIQ-Lite and SIG Lite standards, and automating questionnaire responses with a Make flow that handles 70% of questions automatically while routing the rest for human approval. Jordan covers the two industry-standard "lite" frameworks most mid-market buyers accept, shows exactly which artifacts to publish (SOC 2 links, DPA templates, subprocessor lists), and explains how to triage questionnaires into three risk tiers so you only escalate when truly necessary. He also addresses when this approach breaks down—regulated data scenarios that require full SIG Core responses—and how to charge for deeper reviews as a line item rather than free pre-sales work.

  9. 25

    Production RAG That Actually Works: Supabase pgvector with Bounded Corpus and Auto-Refresh

    Most private RAG deployments fail not because of the model, but because of three fixable infrastructure problems: stale embeddings from unchanged source documents, unbounded corpora that contaminate results with irrelevant content, and no retrieval guardrails to catch bad matches before they reach the LLM. This episode walks through building a production Supabase pgvector RAG system that solves all three: automatic re-embedding when source documents change, bounded corpus design, and SQL-level retrieval gates that block the LLM call when similarity scores are too low or keyword overlap is insufficient. You'll get the complete schema, indexing strategy, refresh pipeline using Make.com or n8n, and the exact cost breakdown for running this on Supabase Pro.

  10. 24

    Build a Regression Gate: Test Sets and Pass-Fail Thresholds for LLM Changes

    When a two-word prompt change can approve fourteen spam submissions in one weekend, you need more than eyeballing outputs. This episode builds a regression gate—a frozen test set, three types of automated checkers, and a pass-fail threshold that blocks deploys when something breaks. The whole system runs inside Promptfoo, triggered from Make or n8n, and takes about forty-five minutes to set up from scratch. You'll get the exact CLI commands, environment variables, and exit code logic to catch prompt regressions before your clients do.

  11. 23

    Why You Don't Need to Self-Host LLMs for Enterprise Clients

    Most solo operators assume they need to self-host LLMs when enterprise prospects mention "on-prem" requirements. But you can satisfy 90% of enterprise security questionnaires without touching a single GPU driver. Jordan walks through the four controls that replace self-hosting: BYO API keys per tenant, region-pinned endpoints, structured logging with correlation IDs, and a visible kill switch in the client portal. You'll get the exact provider settings for Azure, OpenAI, Vertex AI, and Anthropic, plus a one-page checklist you can send to procurement the same day you get the ask.

  12. 22

    Build a Client Control Surface with Airtable + Softr

    When clients text you at midnight asking to turn off automations, you've hit the client proof problem. This episode walks through building a minimal control surface—not a full portal—that gives clients on/off toggles, SLA status chips, and a panic switch using Airtable + Softr + Make. Total build time under a day, total cost under $140/month. You'll get the exact schema, webhook wiring, and role-based visibility setup, plus a Notion + Super fallback for read-only clients. No custom code, no complex auth—just proof and control for the two things clients lose sleep over: is it working, and can I stop it if it's not.

  13. 21

    Your 60-Second Rollback Plan for No-Code Workflows

    Solo automation consultants running Make, Zapier, or n8n in production face a hidden risk: every platform has version history, but each has gaps that will cost you time, money, or client relationships during an actual incident. This episode delivers semantic versioning for no-code workflows, Git-backed exports that work on free tiers, and practiced 60-second rollback drills for each platform. Jordan walks through the exact system that saved him from a costly HubSpot sync failure and shows you how to build rollback-on-demand into your client automation practice.

  14. 20

    Build Tamper-Evident Run Logs: One ID, Full Audit Trail

    Learn to build a complete data lineage automation system using correlation IDs, append-only logs, and exportable evidence. Jordan covers three implementation stacks - Airtable with permissions and interfaces, Notion with integration-only writes, and Postgres/Supabase with hash-chained tamper evidence. Plus a Slack slash command that answers "what happened on this run" with timestamps and status codes in under three seconds. Turn invisible automation work into defensible, auditor-ready evidence that shifts client conversations from "trust me" to "here's the proof."

  15. 19

    Build a PII Redaction Subflow That Logs Every Detection

    Solo operators running Make or n8n workflows that touch client data face a hidden risk: PII and secrets leaking through LLM calls, API requests, and workflow logs. While vendors offer inconsistent protection—Vertex AI has non-configurable filters, Bedrock Guardrails cost per request, and Anthropic relies on prompt patterns—you need a solution that works everywhere and proves it's working. This episode walks through building a detect-mask-log subflow that drops in before any external call. Using Microsoft Presidio or OpenAI's new Privacy Filter, you'll scan for emails, phone numbers, API keys, and other sensitive data, then mask or pseudonymize it based on rules you control. The real game-changer is the annotated log—a JSON object that records what was found, what was masked, and which detector version ran. Jordan covers the cost math between self-hosted detection ($5-15/month in compute) versus managed services (AWS Comprehend's per-character billing, Google DLP's per-GB pricing), addresses the quality tradeoffs of masking versus pseudonymization, and shows how to fail closed when detection errors occur. You'll get the exact subflow templates for Make and n8n, plus the log schema that turns invisible security work into client-visible protection.

  16. 18

    Policy as Code JSON: Enforce Consent and Regions in Every Flow

    Turn your compliance policy from a PDF promise into executable rules that gate every API and LLM call in your Make and n8n workflows. This episode shows you how to encode consent flags, data residency requirements, and tool allowlists as JSON, then evaluate them at runtime using JSONLogic or json-rules-engine. Jordan walks through the complete implementation—from policy file structure to Code step evaluators to fail-closed routing with Slack approval overrides. You'll see specific examples for OpenAI's regional endpoints, Bedrock's model ID prefixes, Vertex AI's region processing, and Azure's deployment types. By the end, you'll have a governance layer that proves compliance during procurement audits and prevents policy drift across client workflows. Includes the Governance-as-JSON Starter Pack with copy-pasteable policy templates and evaluator snippets for both platforms.

  17. 17

    Ship Enterprise SSO on Softr This Week Using Auth0 or Clerk

    When enterprise buyers require SSO for your portal builds, you can ship SAML and OIDC authentication in under a week using a hosted identity provider. Jordan walks through the exact setup for Softr portals using Auth0 or Clerk as the authentication layer, including the critical ACS URL configuration that trips up most first attempts, a complete test plan for both SP-initiated and IdP-initiated flows, and the fallback strategy that keeps deals alive when SSO breaks during pilots. Also covers what's different on Glide and Retool, plus the three scoping questions that prevent you from over-engineering when clients just want Google login.

  18. 16

    1Password vs Doppler: Solo Secrets Management That Scales

    Solo automation consultants face a growing secrets management problem: API keys scattered across Make connections, n8n credential stores, and personal vaults with no audit trail or rotation strategy. Jordan breaks down the 1Password vs Doppler decision for teams of one, showing how to implement per-client scoping, automated rotation reminders, and centralized access logging. Learn the two-tier rotation strategy that aligns with AWS Config defaults, how to use Make teams and n8n projects for blast radius control, and why the proxy pattern matters for LLM integrations. Includes the complete Solo Secrets SOP with ready-to-copy Make and n8n Slack reminder snippets.

  19. 15

    Build a Trust Center That Wins Enterprise Deals

    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.

  20. 14

    Never Get Surprised by AI Bills Again: Throttle + Kill Switch

    Jordan shares the exact guardrail system he built after a $230 Zapier overage nearly cost him $700 in margin. You'll get a unified cost ledger that tracks LLM tokens, Zapier tasks, and Make credits per client, with Slack alerts at 60/80/100% of budget. Plus auto-throttle rules using Delay After Queue, n8n concurrency caps, and Make's built-in backoff—and kill switches on all three platforms that shut down non-critical automations before they eat your margin. Includes the complete template pack with alert formulas and platform-specific toggle recipes.

  21. 13

    Stop Writing Specs: Generate and Validate with JSON Schema Before You Build

    Turn messy client paragraphs into validated, build-ready specs using LLM JSON schema workflows. Jordan walks through the complete system: generate structured specs with OpenAI/Claude/Gemini Structured Outputs, enforce them with JSON Schema validation before any build begins, and auto-create Notion checklists from validated specs. Covers implementation paths for Make (external validator via HTTP) and n8n (Code node with Ajv or HTTP to microservice), plus the Cloudflare Worker setup that makes cross-platform validation portable. No more rewriting specs halfway through builds—the validator catches contradictions, missing fields, and impossible constraints before you touch a single module.

  22. 12

    Safe AI Email Triage: Extract, Classify, Route with Confidence Gates

    Build a production-grade AI email triage system that safely automates 80-90% of your inbox while protecting against costly misroutes. Jordan walks through the Extract → Classify → Route pattern with confidence thresholds, deterministic overrides for high-risk emails, and provider-specific rate limiting across Make, Zapier, and n8n. Learn to respect Gmail's 15,000 quota units per minute and Exchange Online's 30 messages per minute caps while implementing exponential backoff and human-review queues. Includes downloadable JSON schema, confidence rubric, and Slack alert templates.

  23. 11

    Airtable, Notion, or Postgres? Pick the Right Data Layer

    How many of your automations are one rate-limit change away from breaking? Jordan breaks down the decision framework for choosing between Airtable, Notion, and Postgres (Supabase) based on workload shape—not hype. Learn the exact throughput ceilings, concurrency limits, and cost breakpoints that determine which tool is right for your automation stack. Includes real client examples and a calculator to run your own numbers.

  24. 10

    Universal Run Log + Slack Alerts in 90 Minutes

    Build a universal automation monitoring system that catches failures before your clients do. Jordan walks through creating a Notion run log database that every workflow in your stack writes to, plus a Slack alerting layer that respects rate limits and only pings you on actual failures, duration spikes, and consecutive error patterns. The complete build takes 90 minutes, works across Make, Zapier, and n8n, and ensures you'll never learn about a broken workflow from a client email again. Includes the exact database schema, Slack app configuration, and post-run webhook snippets for immediate implementation.

  25. 9

    Four Production Controls That Let You Sleep Through Client Traffic Spikes

    If you're running ten or more Zaps, scenarios, or n8n workflows across client accounts without production-safe controls, you're one API hiccup away from a weekend you can't get back. Jordan walks through the four essential controls every automation consultant needs: idempotency keys to prevent duplicate runs, explicit retry logic that works when platforms fail you, a dead letter queue for clean error recovery, and circuit breakers to contain cascading failures. You'll see exactly where to toggle these settings in Zapier, Make, and n8n, plus the SQL and snippets to implement them across your entire client stack in about four hours.

  26. 8

    Turn Missed Calls into Booked Consults: Voice Agent with Twilio + Realtime API + Calendly

    Jordan lost an $8,000 project because his phone went to voicemail while he was in deep work. By December, he had built a Twilio voice AI agent that picks up every call, qualifies leads with natural conversation, and books consultations directly into Calendly. No receptionist, no VA—just a Node server, OpenAI's Realtime API, and about six hours of build time. This episode walks through the complete implementation: Twilio Media Streams setup, bidirectional audio handling, the critical barge-in pattern that makes interruptions feel natural, Calendly API integration for seamless booking, compliance requirements for call recording, and essential guardrails like DTMF fallbacks and human handoff options. Jordan covers the technical gotchas, latency considerations, and post-call automation that creates Notion summaries and follow-up workflows. Perfect for solo consultants who need to capture every lead without breaking focus on client work.

  27. 7

    Bill AI Usage Without Losing Margin: Stripe Meters + Token Billing

    Every month you run AI for clients on a flat retainer, you're subsidizing their usage with your margin. The gap between what the models cost and what you charge only widens as clients adopt the tools you built for them — success makes the problem worse. This episode shows you how to fix that with Stripe usage-based billing: meters, pricing plans, rate cards, and two concrete implementation paths so that by next invoice cycle, every token has a price and every client pays for what they actually use. We'll walk through setting up Stripe Meters with model and token type dimensions, creating pricing plans with automatic credits, and implementing both the zero-code Vercel AI Gateway path and the self-posting Make/n8n approach. Plus budget controls, Smart Retries for failed payments, and edge cases like backfill and usage caps.

  28. 6

    Never Ask for Passwords Again: Secure Client Credential Intake with Make Credential Requests

    Solo automation consultants face a dangerous liability: storing client passwords in Slack DMs, Google Docs, and email threads. One breach exposes every credential you've ever handled. Make's Credential Requests feature eliminates this risk entirely by letting clients authorize their own apps through secure OAuth links. Jordan walks through building a complete 4-scenario system: automated request creation, status tracking in Notion, 24/72-hour auto-nudges, and proper credential teardown when projects end. Includes handling for Enterprise compliance, non-OAuth apps using 1Password/Bitwarden Send, and addressing the Enterprise/Partner access requirements. The result: secure, trackable client onboarding that protects both you and your clients while eliminating manual password chasing forever.

  29. 5

    Build a Live ROI Dashboard Clients Check Voluntarily (Stripe + Looker Studio + Notion)

    Turn invisible automation work into undeniable ROI with a live client dashboard that updates itself. This episode walks through building a complete Stripe-to-Looker Studio pipeline that shows real money — MRR, time savings converted to dollars, and operations eliminated with price tags attached. Your clients will check it voluntarily, without you asking, because it shows them exactly why they're paying you. We cover three ingestion routes: direct connectors for immediate deployment, Google Sheets staging for cost-conscious solos, and BigQuery for bulletproof scale. You'll get the exact ROI math that makes CFOs pay attention, security settings that prevent data leaks, and the Notion embed pattern that puts everything where clients actually work. By the end, you'll have a self-serve ROI proof machine that eliminates weekly reporting while making renewals automatic. When clients can see their 3x ROI multiple anytime they want, they stop questioning your value and start bragging about their smart hiring decision.

  30. 4

    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.

  31. 3

    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.

  32. 2

    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.

  33. 1

    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.

  34. 0

    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.

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ABOUT THIS SHOW

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.

HOSTED BY

Jordan

Frequently Asked Questions

How many episodes does Headcount Zero have?

Headcount Zero currently has 34 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Headcount Zero 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.

How often does Headcount Zero release new episodes?

Headcount Zero has 34 episodes. Check the episode list to see recent publication dates and frequency.

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Who hosts Headcount Zero?

Headcount Zero is created and hosted by Jordan.
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