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The plan over time (plain version)

The detailed roadmap with diagrams and triggers is in ../business/roadmap.md.

We grow in steps. Each step starts when the app is ready and users are asking for it — not on a fixed calendar.

graph LR
    A[1. Free app<br/>on your computer] --> B[2. Optional extras<br/>backup + easy AI]
    B --> C[3. Coaches & schools<br/>help more people]
    C --> D[4. Prove your history<br/>with your permission]
    D --> E[5. Big partnerships<br/>the Common App for jobs]
    style A fill:#e8f5e9,stroke:#2e7d32
    style B fill:#e3f2fd,stroke:#1565c0
    style C fill:#e3f2fd,stroke:#1565c0
    style D fill:#fff3e0,stroke:#ef6c00
    style E fill:#f3e5f5,stroke:#7b1fa2

Step 1 — The free app

A helper on your own computer that fills out applications, polishes your resume, and tracks everything. Free, private, always. Goal: earn trust and help real people.

Step 2 — Optional extras

For people who want it: backup, syncing across devices, and a "just works" AI option. Goal: our first income, without giving up privacy.

Step 3 — Coaches and schools

Career coaches, bootcamps, and universities use WorkWingman with the people they help — and can see their progress only if the job seeker agrees to share. Goal: steady income from groups that want people to succeed.

Step 4 — Prove your history (only with your permission)

A private "wallet" where you can collect proof of your jobs and degrees, and share it when you choose. No repeating background checks. Goal: make trust portable.

Step 5 — Big partnerships

Once lots of people love the app, we work with big job platforms so your one profile works everywhere — the "Common App for jobs." Goal: the big vision, done from a position of strength.

What never changes

  • The free app stays genuinely useful.
  • You're always in control — it never applies without you.
  • Your data stays on your computer unless you choose otherwise.
  • We're always on the job seeker's side.

How the money works: money-plan.md