Contractor Continuity Plan
Executive Summary
Three contractors each sole-maintain critical systems with no documentation, no backup, and unknown contract notice periods. Federico Del Rio (Nearsure) has 374 commits on the Members Portal — the only person who can operate it. Jonathan Perez (DualBoot) sole-maintains the RPM Planner across web, backend, and mobile. The Nearsure contract notice period is unknown to the CTO.
If either contractor gives notice tomorrow, we have zero effective warning time. The fix is a 4-week documentation sprint producing 6 artifacts per system, combined with designated backups for each critical system and Doppler for secrets management (replacing scattered .env files).
What Needs to Happen
Six Artifacts Per System
- README — Setup-from-scratch guide (new engineer can run locally in <1 hour)
- Architecture Decision Records (ADRs) — Why things were built the way they were
- System Context Diagram — Mermaid diagram showing integration points
- Environment Variable Manifest — Every env var, what it does, where it comes from
- Operational Runbook — Top 5 failure scenarios with step-by-step resolution
- Dependency Map — External services, APIs, databases with ownership and contacts
- Week 0: Review Nearsure and DualBoot contract notice periods — Owner: Lior. This week. Critical: we don’t know how much warning we get.
- Week 0: Access audit — Verify all contractor accounts, enumerate what they own. Every system, every credential, every deployment path.
- Week 1: Federico documents Members Portal — README, architecture, env manifest. Named backup: Josh Fuller.
- Week 2: Jonathan documents RPM Planner + Freddy documents AI tools — Same 6-artifact template. Named backups coordinated with Justin/Alex (RPM) and Jay + Johnny (AI).
- Week 3: CI/CD integration — Verify named backups can run each system from documentation alone. No tribal knowledge required.
- Week 4: Validation — Named backup performs a supervised deployment using only the documentation. If they can’t, documentation is incomplete.
Claude Code acceleration: Auto-generated documentation from codebase analysis is one of AI’s strongest capabilities. Claude Code can analyze repository structure, infer architecture, generate README templates, produce Mermaid diagrams from import graphs, and extract environment variable manifests from code. Estimated savings: 1-2 weeks from the original 4-week timeline.
Completion Criteria
- Nearsure and DualBoot contract notice periods documented
- Full access audit completed — all contractor accounts and ownership enumerated
- Members Portal: all 6 artifacts complete (README, ADRs, context diagram, env manifest, runbook, dependency map)
- RPM Planner: all 6 artifacts complete
- AI tools: all 6 artifacts complete
- Josh Fuller can independently deploy and operate Members Portal using documentation
- Named backup for RPM Planner verified through supervised deployment
- Doppler deployed — all
.envfiles migrated to centralized secrets management - Validation exercise complete: each named backup operated their system independently
Initiative Attributes
Tools Required
| Tool | Purpose | Cost |
|---|---|---|
| Doppler | Centralized secrets management — replaces scattered .env files across systems | $50/month |
| Mermaid | Architecture diagrams embedded in repos — system context diagrams for each system | Free (OSS) |
| Swimm | Documentation with CI stale-doc checks — ensures docs stay current as code changes | $8/user/month |
Related Risks
| ID | Risk | Severity | Probability | Mitigation |
|---|---|---|---|---|
| RF2 | Federico contractor departure (Nearsure) | HIGH | UNKNOWN | D8 captures knowledge. Josh Fuller as named backup. H4 Integration Engineer as backstop. Review Nearsure contract notice period THIS WEEK. |