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WorkWingman — Plain-Language Overview

Think of WorkWingman as a capable assistant sitting at your desk who fills out job applications for you, shows you everything before sending, and never uploads your life to a website.

It runs entirely on your own Windows computer. Nothing about you gets shipped off to some company's servers. The assistant does the boring, repetitive parts of job hunting — but you stay in charge, and you see everything before anything is submitted.

What it does, in five steps

flowchart TD
    A["1. Reads your saved<br/>LinkedIn jobs"] --> B["2. Writes a tailored resume<br/>+ cover letter in your voice"]
    B --> C["3. Fills the application<br/>while you watch<br/>(pauses to ask when unsure)"]
    C --> D["4. Helps you study<br/>for the role"]
    D --> E["5. Tracks who you applied to<br/>and your interviews"]

  1. It reads your saved LinkedIn jobs. You save jobs on LinkedIn like normal. WorkWingman picks them up — oldest first, so nothing falls through the cracks.

  2. It writes a tailored resume and cover letter in your voice. Not a generic template. It draws on the background you tell it about (there's a "Your story" screen for exactly this) so the documents actually sound like you.

  3. It fills the application while you watch — and pauses to ask when it isn't sure. The application opens in a browser window right in front of you. You can see every field being filled. If it hits something it isn't confident about, it stops and asks you, giving you a short list of options ranked best-first. Whatever you choose, it remembers so it won't ask again.

  4. It helps you study for the role. For each job it builds a little study plan — links to docs, YouTube, Udemy, Google Skills Boost, AWS Skill Builder, Microsoft Learn, LeetCode, Medium, and optionally a Claude study project — so you can prep for interviews.

  5. It tracks who you applied to and your interviews. It keeps a record of every application and puts your interviews on your Google and Apple calendars, so you never lose the thread.

The promises it keeps

These aren't optional settings you might accidentally turn off. They're built into how the app works:

  • It never sends anything on its own. The final "Submit" always waits for you. There is no button, anywhere, to let it submit without your say-so.

  • When it's unsure, it asks — it doesn't guess. If it isn't confident about a field, it pauses and hands you a short, ranked list of choices. Your answer sticks, so you're never asked the same thing twice.

  • Your passwords stay locked away. Secrets live in a secure vault (KeePass) on your machine. They are never handed out over the app's internal connection — the part of the app that fills forms reaches into the vault directly, only at the exact moment it's needed.

  • Everything lives on your computer. Your data is stored in files on your own machine — that's the real copy. If you connect Google Drive or Sheets later, that's just a backup, not the home base.

  • It cheers you on. Job hunting is draining, so the app sprinkles in encouraging notes and celebrates your milestones. Small thing, but it's on purpose.

A quick word on setup

The first time you open it, WorkWingman does a health check — it makes sure the few tools it needs are installed and up to date. If something's missing, it offers to install or fix it, but only after you approve each item one by one. It never installs anything behind your back.

Roadmap (not yet built)

A few parts are still placeholders — they're wired up so the app runs, but the real version isn't finished yet. Today, these do not fully work:

  • Connecting to your real Google account (Calendar / Sheets backup).
  • The permanent, encrypted password vault on disk (right now it uses temporary sample data).
  • The truly custom, AI-written resume and cover letter (right now it uses a stand-in draft).
  • Automatically spotting interview invites in your Gmail.
  • The live, watch-it-happen browser window (right now that area shows a placeholder).

We'll only call these "done" once they actually are.