TSYS Group COO 6c7cb6bb52 docs: add resume-prompt.md for session 2 handoff
Comprehensive handoff document covering:
- What works (BW host CLI, bw_helper.py lifecycle safety)
- What's broken (container BW sync, 2FA, Redmine/Discourse SSO)
- Cloudron Pankow UI patterns (keyboard.type, role=button)
- Per-app SSO button selectors
- Mistakes from session 1 to avoid repeating
- Suggested first actions (fix BW sync before Playwright)

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2026-09-07 14:51:13 -05:00

org-buildout

Building an AI-native organization — shared transparently as a bootstrapping reference.

This repository documents the full thought process behind TSYS Group's transition from a solo-founder operating model to an AI-agent-augmented organization. It captures the planning, architecture decisions, and operational design work behind:

  • COO → CTO transition — delegating operations to AI agents + a human COO
  • AI agent identity architecture — Cloudron SSO, Bitwarden credential management, per-agent RBAC
  • Infrastructure buildout — Proxmox fleet, k8s cluster, monitoring, zero-trust networking
  • Security/compliance targets — CMMC L3, STIG, ITAR, zero trust

Why public?

My brand (@reachableceo) is about reachability and transparency. Most organizations hide their internal operations. I'm sharing the full process — the messy early stages, the planning docs, the architecture decisions — because I believe the future of work involves AI agents as first-class organizational members, and showing how that gets built is more valuable than hiding it.

Documents

Document What it covers
prompt.md Q2/Q3 2026 planning notes — org chart, AI team roles, goals, SDLC/process requirements
prompt-techops.md IaC testing model — sectestbed/preprod VM workflow
prompt-k8s.md K8s vision — VCluster, Rancher, multi-tenancy, workload catalog
transition-map.md Full transition map — current state across Redmine/Discourse/Gitea/infrastructure, Q3/Q4 timeline, risk register, open decisions
agent-identity-bootstrap.md Agent identity provisioning plan — Cloudron enrollment, API key generation, Bitwarden credential architecture, Playwright automation design

Agent Resources

File What it covers
AGENTS.md Orientation guide for agents working in this repo
STATUS.md Current state, blockers, next actions (agent-maintained)
questions-v1.md Open questions for Charles (edit inline to answer)

Context

  • TSYS Group is the overall organization (multiple business entities under one umbrella)
  • Known Element Enterprises (KNEL) owns and operates all IT/business systems
  • The environment operates in ITAR/CMMC/TS/SCI compliance space
  • The infrastructure is a Proxmox bare-metal cluster in a private residence
  • The production stack runs on Cloudron (Reston VA VPS) + on-prem k8s

Status

This is live, evolving documentation. The transition is in progress (Q3-Q4 2026).

License

GNU Affero General Public License v3.0. See LICENSE.

S
Description
Building an AI-native organization — full thought process, planning docs, and transition maps for TSYS Group's COO→CTO handoff and AI agent identity architecture.
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