Foundation type
501(c)(3)
non-profit, US
I.What this is
A set of four documents describing The Cloudbase Foundation's technology strategy — what is being built, who is building it, where it lives, and why each piece exists. This page exists so that anyone arriving cold can find the right entry point.
The Cloudbase Foundation is a 501(c)(3) nonprofit supporting the free-flight community: paragliding pilots, hang glider pilots, competition organizers, and the volunteers who make safe events possible. The organization runs lean. Technology investments are evaluated on whether they reduce manual work for staff and partners, increase visibility into donor and project relationships, and contribute back to the wider open-source ecosystem.
These documents capture the working strategy that emerged from a series of design conversations between Jonathan (CBF director) and Claude Code in May 2026. They are written to be read in any order — each is self-contained — but they are most useful read together.
Core principle
Open + self-hosted
minimal SaaS lock-in
Primary stack
Twenty + Next.js
Donorbox for donations, ListMonk for email
Repos
4
CBF-site · CBF-crm · chelan-comps · documents
II.The documents
Three companion documents sit alongside this one. Each one has a distinct job; together they cover the strategy from intent through execution to infrastructure.
Doc 01
Roadmap
What ships in each phase and the architectural decisions behind it. Phase 1 (complete) through Phase 6 (donor communications), with explicit "what changed and why" callouts where the plan has evolved.
Doc 02
Project Timeline
Operational breakdown. For every task in every phase: who owns it (Claude or Jonathan), rough token and time estimates, and which Claude Code agents and skills are appropriate. Includes a Gantt chart of the sequencing.
Doc 03
Domain Map
URL surface. Every subdomain under cloudbase.foundation, what service backs it, when it comes online, and the conventions governing naming and hosting. The canonical reference when adding a new URL.
III.Suggested reading paths
The documents are written so they can be skimmed selectively. These pathways correspond to the most common reasons someone opens this folder.
Board member or grant funder
Read this page, then Roadmap §I & §II (executive summary and current state). If you have ten more minutes, skim Project Timeline §I & §V (effort budget). You will have a complete picture of strategy and cost without needing to read about webhooks or matching algorithms.
Prospective technical collaborator
Read all four documents in order. Roadmap explains what; Project Timeline explains how the work splits; Domain Map explains where things live. Then look at the supporting analysis docs in the
CBF-crm/docs/strategy/ folder for the deeper context behind specific decisions.
Comp organizer considering forking Groundcrew
Roadmap Phase 4 is the one to read — it describes the OSS-ification plan for the volunteer app. Once the dedicated Groundcrew docs ship at
groundcrew.cloudbase.foundation, that will be the better entry point. The existing production install lives at chelancomps.org.
Another Twenty-stack builder (e.g. James's nonprofit-crm-stack)
Roadmap §III covers the execution-surface split between sidecar service, Twenty App, and Cloudflare Workers — that is the part most worth comparing notes on. The
contribution-strategy.md and donor-matching-considerations.md docs in CBF-crm/docs/strategy/ articulate where CBF's and James's work could share dependencies (notably the matching library).
Future CBF director or staffer
Start with Domain Map — the URL map will orient you to the entire stack faster than anything else. Then Roadmap §II for current state, and Project Timeline §IV for the operating cadence with Claude Code.
IV.How the work gets done
The execution model is a director-plus-AI pair: Jonathan directs and approves, Claude Code handles the bulk of the implementation. The pattern resembles having a full-time engineering team available on demand, with the trade-off that direction must be explicit and verification rigorous. Jonathan picks the strategy, validates the output, and handles everything that requires credentials, in-person decisions, or relationship work (donor communications, board interactions, partner outreach). Claude builds, tests, configures, and documents.
This pattern is sustainable because the surface area of work is bounded. CBF is not building a SaaS company — it is configuring and integrating well-defined components: a CRM, a donation platform, an email platform, a website, a volunteer app. Each component has a documented integration story. The hard part is choosing the right components and wiring them together carefully, which is exactly the kind of work where careful AI assistance is genuinely valuable.
Where the documents live
These four files are stored in the Cloudbase-Foundation/documents repo under tech/. They are companion HTML files — static, no build step, no JavaScript dependencies beyond Mermaid for the diagrams. View them locally by opening the file directly, or on GitHub. The plan is to eventually serve them under board.cloudbase.foundation via Pages CMS.
Revision conventions
Each document carries a revision number and date in the masthead. When the underlying decisions change, the affected document is bumped (Roadmap is currently at Rev. 2) and a "what changed and why" callout is added inline. The Strategy Brief (this page) is Rev. 1 and will be revised as new documents join the set or major scope changes ripple across multiple docs.
Supporting analysis documents
The four documents in this folder summarize and direct. The detailed analysis behind their conclusions lives in Cloudbase-Foundation/CBF-crm/docs/strategy/ — including donor-matching-considerations.md, donation-platform-comparison.md, contribution-strategy.md, and the original drafts. Those are working documents, not finished artifacts, and they evolve as Jonathan and Claude iterate.
V.Related repositories
All under the Cloudbase-Foundation GitHub organization.
- CBF-site — the public Next.js website at
cloudbase.foundation. Tina CMS for content; OpenNext + Cloudflare Workers for hosting. - CBF-crm — infrastructure and documentation for the Twenty CRM instance. Holds the data model definition, the supporting strategy documents, and the Python helper scripts that keep the data model in sync between repo and CRM.
- CBF-kanban — deployment config, env template, nginx, and runbook for the self-hosted kan internal kanban board, running alongside the CRM on the Unraid VM (
kan.cbf-dev; prodkan.cloudbase.foundation). New June 2026. - chelan-comps — production volunteer-application app at chelancomps.org. Will be generalized as the OSS Groundcrew product during Phase 4.
- documents — this repository. Meeting agendas, board materials, and the
tech/strategy folder.