WorkWingman — Business & Strategy Docs¶
Living documents. These capture the plan, not a contract. They evolve as we learn. Every figure that came from research is sourced; every figure we invented for planning is labelled an assumption.
This folder is the business/legal/technical-detail track. Each doc has a plain-language mirror in ../plain/ for everyday readers (family, non-technical teammates, students). Same idea, two depths — the same convention the rest of the docs follow.
The one-sentence version¶
WorkWingman is a free, local-first, privacy-first job-application Career Concierge that helps a person run their whole job search from their own machine — and becomes the trusted "Common App for jobs" without ever becoming a spam cannon or selling anyone's data.
Start here¶
| I want to… | Detailed (this folder) | Plain-language |
|---|---|---|
| Pitch it in one breath | elevator-pitch.md | ../business-plain/elevator-pitch.md |
| Get the whole thing on one page | executive-summary.md | ../business-plain/business-overview.md |
| Understand the competitive landscape | competitive-analysis.md | ../business-plain/competitive-analysis.md |
| Understand how we make money (and why in that order) | monetization-strategy.md | ../business-plain/money-plan.md |
| See the staged plan over time | roadmap.md | ../business-plain/roadmap.md |
| Check the numbers: pricing, costs, ROI, break-even | financial-model.md + financial-model.xlsx | ../business-plain/money-plan.md |
| Test assumptions and verify claims before decisions or presentations | venture-evidence-ledger.md | — |
| Present it to an investor or partner | pitch-deck.md + pitch-deck.pptx | — |
| Pitch a testing/pilot partner (Adaptive Solutions) | adaptive-solutions-pitch.md + adaptive-solutions-pitch.pptx | — |
| Know how we go to market and stay trusted | gtm-positioning.md | ../business-plain/how-we-grow.md |
| Understand the legal / compliance guardrails | legal-compliance-risk.md | ../business-plain/staying-legal-and-safe.md |
| See where the strategy came from | council-verdict.md | — |
| Check AI-generation unit economics, caps (WING-299) and top-up packs (WING-300) | ai-generation-economics.md | ../plain/ai-generation-strategy.md |
| See the founding-team offers (cofounder/C-suite first, advisor fallback) | founding-team-recruitment.md | ../business-plain/founding-team-recruitment.md |
Evidence governance¶
The venture evidence ledger governs claims about customer demand, traction, pricing, channels, and business-model risk across these documents. Use it before changing a roadmap stage gate, promoting a financial assumption, making a go-to-market decision, or publishing an investor or partner claim. Interviews, observed behavior, commitments, product outcomes, market research, and comparable-company context must remain distinguishable.
Markdown remains the source of truth for every presentation. Before regenerating a .pptx, verify its material claims against the ledger, preserve all qualifications, and keep private participant data out of both the repository and the rendered deck.
The three things that must never be forgotten¶
- Don't become "auto-apply at scale." That brand is what gets tools platform-banned and hated by employers (LazyApply / Sonara / JobRight territory). We are a trusted candidate operating system, quality over quantity.
- Partnerships and verification come last, not first. LinkedIn/Workday deals need leverage we don't have yet; verification is FCRA legal territory. Earn the user base first.
- Solve the structural churn. Job seekers leave the day they get hired. Non-churning institutional (coach/school/org) seats + repositioning to lifelong career management is how the business survives that.
Provenance¶
The strategy here was produced by a multi-model council (Codex/gpt-5.5 with live web research, Gemini, and two local open-model councils) chaired and synthesized on 2026-07-06, then deepened with dedicated research agents on financials, go-to-market, and legal/compliance. See council-verdict.md and ../../../llm-council/reports/COUNCIL-LOG.md.