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How WorkWingman is put together (plain version)

Think of WorkWingman as a capable assistant sitting at your desk — not a website you upload your life to. Everything runs on your own computer. The assistant has three parts working together, and a few outside services it talks to on your behalf.

Engineer version with real diagrams: ../technical/architecture.md

The three parts

  • The window (Electron) — the app you actually open and click around in. It starts up the other two parts for you and shows them in one tidy window.
  • The face (Angular) — the screens you see: your job queue, the live application view, your settings, and so on.
  • The brain (a small local server, .NET) — does the real work: remembers your answers, logs into sites, fills in applications, and keeps your secrets in a locked vault. It only listens to your own machine — nothing on the internet can talk to it.

The five steps it does for you

The five things WorkWingman does for you

flowchart LR
    A["1 · Reads your<br/>saved LinkedIn jobs"] --> B["2 · Writes a tailored<br/>resume + cover letter"]
    B --> C["3 · Fills the application<br/>while you watch"]
    C --> D["4 · Helps you study<br/>for the role"]
    D --> E["5 · Tracks who you<br/>applied to + interviews"]
  1. Reads your saved jobs from LinkedIn, oldest first, so nothing expires before you get to it.
  2. Writes your documents — a resume and cover letter tuned to each job, in your own voice.
  3. Fills the application while you watch. For Workday jobs it drives a real browser you can see, and it pauses to ask you whenever it isn't sure. For other sites it hands you the answers to copy and paste.
  4. Helps you study — it gathers documentation, videos, and courses that match the job, and can spin up a focused Claude study workspace.
  5. Keeps track of everything you applied to, and puts your interviews on your Google and Apple calendars.

The best-of-both-worlds way it fills out forms

For Workday-style applications, the app mostly drives itself using a big list of "clues" it's learned for that website (which box is the first-name box, which button is Next, and so on — see the making-of story for how those clues were learned). That part is fast and free.

But sometimes a field is genuinely unclear — a question this particular company made up that nothing has seen before, or a dropdown with no obviously-right option. For just those moments, the app can ask a Claude-powered helper that's looking at the same page to suggest the best answer. The helper only gets asked when the app is actually stuck, so it stays fast and cheap the rest of the time — and if even the helper's best guess isn't confident enough, the app still stops and asks you, exactly like it always has. See the engineer version for the technical seam.

The promises it keeps

  • It never hits "submit" without you. You always get the final say.
  • When it's unsure, it asks instead of guessing — and remembers your answer next time.
  • Your passwords stay in a locked vault on your machine. The app only borrows them long enough to log in, and never shows them on screen.
  • Everything lives on your computer. Google Drive is just an optional backup.
  • It cheers you on. Job hunting is draining, so it offers encouragement along the way.
  • If the local brain is still waking up, the face quietly waits and retries for safe read-only requests, and tells you plainly if it still can't reach it — but it never re-sends an action like starting an application, so nothing gets submitted twice.