Connect Claude to WaypointCareer

You can let Claude work inside your WaypointCareer account: read the jobs you are interested in, draft a tailored resume and cover letter for one of them using your own templates, and record what you applied to.

You talk to Claude; Claude talks to WaypointCareer. Nothing is posted to an employer, and nothing is marked applied unless you say you submitted it.

Available on any paid plan. On the free plan the connector will connect but every action refuses with an upgrade message.

Before you connect

Set these up once, under Settings → Application Documents:

  1. A resume template — how your tailored resumes should be built.
  2. A cover letter template.
  3. At least one uploaded resume.
  4. A label on each resume if you have more than one, so Claude knows which to start from ("Platform leadership", "Use for infra and platform org roles").

Nothing is preconfigured on purpose. Until these exist, Claude will tell you exactly what is missing rather than guessing.

Connect it

Your connector URL is shown, ready to copy, at Settings → Application Documents → Agent connector.

In Claude (web or desktop) or Cowork:

  1. Settings → Connectors → Add custom connector.
  2. Paste the URL. Leave Client ID and Client Secret empty — there is no key to create and nothing to copy from WaypointCareer.
  3. Save, then Connect. A WaypointCareer sign-in page opens.
  4. Sign in if you are not already, then read the three permissions and Approve.

If you are on a Claude Team or Enterprise plan, your workspace owner may have to add the connector for the organisation first. Once they have, each person connects their own WaypointCareer account to it — your jobs and documents stay yours.

In Claude Code:

claude mcp add --transport http waypointcareer <your connector URL>

The first time Claude uses it, the same sign-in and approval happens in your browser.

What you are approving

Three permissions, shown on the approval screen:

  • Read your jobs, resumes, document templates and profile.
  • Generate tailored resumes and cover letters, and attach them to a job.
  • Record application questions and answers, skip reasons, and mark a job applied once you confirm you submitted it.

Using it

Ask in plain language — for example:

Which jobs am I interested in? Take the Head of Platform one, draft a tailored resume and cover letter, and show me the draft.

Claude will read the job and your templates, follow the tailoring guidance your WaypointCareer operator has configured, and attach the documents to that job. You will find them on the job in the app, exactly as if you had generated them there.

When you have actually submitted the application, tell Claude and it will mark the job applied. It will not do that on its own — it cannot submit anything for you, and a job marked applied that was never sent would throw off your pipeline and every report built on it.

If you decide against a job, Claude can record the skip and your reason, so the decision is on the record rather than lost in a chat.

Confidential jobs

Jobs you have marked confidential are never sent to Claude — not even with the employer blanked out. Apply to those from the web app.

The reason is honest rather than cautious: the tailoring work needs the posting text, and the posting text is usually where the employer is named. Blanking the company field while sending the posting body would look like privacy without being it.

Seeing and removing connections

Settings → Application Documents → Agent connector lists every client connected to your account, when it connected, and what it can do.

Disconnect cuts one off immediately and completely — it has to be approved again before it can read anything. Use it if you stop using a client, or if you are ever unsure about one.

"Disconnected — reconnect needed"

WaypointCareer cuts a client off by itself if its sign-in token is used twice, because that can mean the token was copied. The client then shows at the top of the panel as Disconnected — reconnect needed.

  • To keep using it, reconnect from Claude (or your other client) the same way you connected it the first time. The notice goes away once it is connected again.
  • If you no longer use that client, select Dismiss. This only hides the notice for you; it doesn't change anything else.

The notice also clears by itself within 30 days.

When something does not work

| What you see | What it means | |--------------|---------------| | "Upgrade required" | The account is on the free plan, or a paid plan has lapsed. Check Settings → Subscription. | | "Setup required" | A template, a resume, or a resume label is missing. The message names it and links to the right tab. | | A message about the platform not being configured | Your WaypointCareer operator has not finished setting the feature up. There is nothing for you to fix — contact support. | | "This job is confidential" | Expected. Apply from the web app. | | Claude says it needs to start a run first | Normal. It re-reads your setup and guidance before writing anything; let it. |