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Editions strategy — why more than one surface exists

Audience: founder, operators, finance, partners who need the why, not the flag names.
Sources: packaging and cloud-run technical contracts, cloud-edition business case, access/cohort design, marketing site content, release notes.
Rule: no invented demand, pricing, or run-rate numbers. Gaps marked TODO(verify).


1. The problem multiple editions solve

WorkWingman has two honest product truths that pull in opposite directions:

Truth Implication
Default product is local-first desktop Privacy story, BYOK AI, full feature depth, data on the user’s machine. Best for real job-search work.
Some audiences will not install a Windows app first YC review, remote teammates, and timed user tests need a browser path with a short menu and hard blast-radius limits.

A single “one binary, one cloud login, full product for everyone” surface would either:

  • force multi-tenant SaaS before storage and routes are tenant-safe, or
  • force reviewers through an installer + local setup that kills first-look conversion.

So the strategy is editioning by risk and audience, not by vanity SKUs.


2. What we actually maintain (and why)

2.1 Public desktop (NSIS installer)

Why it exists

  • Primary product: full HelPeR behavior on the user’s PC.
  • Marketing and packaging promise: one program, one install, no developer toolchain on the tester’s machine.
  • Chromium for vault/login automation ships in the box so “clean laptop” demos do not fail mid-flow.

Cost / benefit

Benefit Cost / risk
Strong privacy and trust story (local-first) Installer size (~hundreds of MB with runtime + browser); SmartScreen until signing reputation
Offline-capable first launch Build complexity (publish API + bundle Chromium + NSIS)
Shareable beta without hosting multi-tenant data Support burden of unsigned or early-signed EXE; update feed must be operated deliberately
electron-updater path for later self-serve updates Feed URL configured but package still flags unpublished build — TODO(verify) live feed ops

Strategic role: default GTM and everyday use. Cloud does not replace it in the current contracts.

2.2 Hosted server edition (invitation + Google cohorts)

Why it exists

  • YC reviewers: bounded evaluation without desktop install.
  • Team testers: parallel invitation-gated surface without pretending the whole desktop repo is multi-user-safe overnight.
  • Internal / user-testing / QA cohorts: Google allowlists so real people get the right workspace and telemetry label (including excluding QA noise from user-testing analysis).

Cost / benefit

Benefit Cost / risk
Browser first look for investors/reviewers/teammates Cloud Run, load balancer, Firestore, Secret Manager, invitation ops
Audience separation (YC vs team codes; cohort isolation) Rate limits, CSRF, session HMAC, secret rotation, live boundary verification
Private workspace per redemption (avoid shared demo chaos) Support for code distribution and revocation
Hard route allow-list / 503 for non-pilot APIs Product looks “thin” next to desktop — must be explained honestly
AI spend brakes on pilot paths Absolute budgets and full COGS still TODO(verify)
User-testing flag for surveys/insights Telemetry governance; multi-tenant legacy store caveats when routes unlocked

Strategic role: private pilot and learning, not yet a claim of full SaaS. Desktop remains the default product in technical and business cloud docs.

2.3 QA / dual-role (“Test Bench” language)

Why it exists

  • QA needs a shared workspace pattern (qa cohort can disable per-member private workspaces).
  • Some people hold two jobs (e.g. Test Bench QA and real user testing). Exclusive cohorts plus a deliberate multi-mode email list force an explicit session choice so telemetry and workspace isolation stay honest.

What we do not claim

  • A formal mock vs live Test Bench product pair is not specified in this repository. Treating “mock/live” as shippable editions would invent structure. Closest real dual axes: cohort mode choice, desktop real/sandbox data worlds, and prod vs qa deployment rungs.

Cost / benefit: better metrics hygiene and dual-role ergonomics vs config complexity and the risk that unknown audiences fall to capability “locked” until mapped.

2.4 Docs audiences (yc-reviewer / team-test) and marketing site tiers

Why it exists

  • In-app docs: fail-closed per document so team-only material never ships to YC review sessions (and vice versa for YC-only fixtures).
  • Marketing site: separate Team / Internal / Tester email tiers for brochure/docs cards — different system, different lists.

Cost / benefit: confidentiality and staged disclosure vs two parallel allowlist systems operators must not confuse. Env-ladder “live-only reader settings” hazard remains TODO(verify) for exact keys.

2.5 Public cloud site (MPA)

Why it exists

  • Brochure, trust, user-testing notice, and CMS-managed content without loading the Angular desktop shell for every visitor.
  • Standing split: htmx/Razor for content, Angular for the product app.

Cost / benefit: clear GTM surface and staff CMS vs another deployable (and a hard requirement that QA content buckets never publish into production).


3. Strategy principles (from the contracts)

  1. Desktop first, cloud second. Server mode is opt-in via config (Edition=server), not the silent default.
  2. Audience is server-derived. Invitation codes and Google allowlists assign policy; the browser must not invent edition from URL or build flags.
  3. Short menu beats fake full product. Pilot routes are mechanically limited; config cannot unlock unsafe multi-tenant legacy stores without an explicit unlock that shares process-wide data (documented hazard).
  4. Separate money brakes from infrastructure bills. AI dispatch caps and GCP budget alerts are different layers; do not sell one as the other.
  5. One desktop artifact. No evidence of a second branded “internal desktop” installer — internal difference is cloud identity/cohort, not a second NSIS product name.
  6. Honest gaps. Missing tester-laptop-distribution-spec.md means laptop fleet logistics are not codified here — TODO(verify) before promising hardware-based distribution programs.

4. Cost / benefit summary table

Surface Main benefit Main cost Keep when… Drop / freeze when…
Desktop NSIS Full product, local trust Build size, signing, support of EXE Real users and power demos need full depth N/A as core product in current strategy
Cloud server pilot Review/test without install Cloud ops, security review, short feature set Need YC/team first look or hosted testing If it is sold as full multi-tenant SaaS without tenant-safe stores
Invitation audiences (YC / team) Policy separation without admin grants Code ops, hash secrets, redemption limits Distinct legal/review vs team needs If a single shared demo account would suffice (it usually does not)
Google cohorts (internal / user-testing / qa) Identity-based access + clean telemetry Allowlist maintenance, multi-mode edge cases Recurring humans, dual roles If everyone is one-off invitation only
UserTesting flag Learning from real sessions Survey fatigue, PII discipline Active tester program Flag left on in non-test deploys without intent
Prod vs QA ladder Blast-radius isolation Double secrets/services Any writeable CMS or tester traffic Temptation to point QA CMS at prod bucket
Docs audience gates Information control Manifest discipline Mixed YC + team readers Public-all docs that never need gating
Marketing editions copy (desktop free / cloud subscription) Clear story on the site Must not over-claim live paid cloud Narrative matches actual offer Copy implies live subscription not yet operated — TODO(verify) monetization status

5. What success looks like (non-revenue)

From cloud-edition business framing and technical contracts:

  • Reviewers and teammates enter only with proper gates, get isolated workspaces where designed, and cannot open non-pilot surfaces.
  • Desktop installers remain shareable for friend/tester laptops without requiring cloud tenancy.
  • Spend and abuse have brakes on pilot AI paths; rollouts fail closed on wrong security topology.
  • Telemetry can separate QA from user-testing cohorts.

Revenue model for cloud SKU, willingness to pay, and rolled-up monthly cloud COGS: TODO(verify) — not established as fixed numbers in the edition contracts.


6. Decision framing

Keep multiple editions while:

  1. Desktop remains the full product and cloud remains a bounded pilot (or later a clearly paid hosted SKU with tenant-safe storage).
  2. Audiences (YC, team, internal, user-testing, QA) still need different data, retention, or metrics rules.
  3. Operators can afford Secret Manager, ladder deploys, and invitation hygiene.

Collapse surfaces only when a single path meets privacy, support, and review needs without silent cross-tenant risk — and document the collapse; do not “simplify” by turning unlock flags on in production multi-tenant hope.


7. Source map

Topic Source
Desktop packaging / updater docs/technical/packaging.md, electron/package.json
Server edition contract docs/technical/cloud-run-server-edition.md
Cloud business case docs/business/cloud-edition-value.md
Cohorts / dual-role docs/design/wing-214-google-sso.md
Docs audiences docs/cloud-docs-manifest.json, docs/technical/oauth-and-reader-tiers.md
Ladder hosts ops/cloud-run/env-ladder.json
Marketing edition cards src/WorkWingman.Site/Content/site-content.json
Release dual-edition narrative docs/technical/wing-202-release.md, docs/plain/wing-202-release.md