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
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	—
See the founding-team offers (cofounder/C-suite first, advisor fallback)	founding-team-recruitment.md	../business-plain/founding-team-recruitment.md

The three things that must never be forgotten

1. 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.
2. 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.
3. 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.