Email & Scheduling

Email and recruiter messages (email-comms)

For any recruiter email, hiring email, or job-search message — drafting, replying, following up, thanking, negotiating in writing, or cold outreach — say:

draft a reply to this / follow up with [Company] / write a thank-you

The email-comms skill:

• Reads the full thread history from workspace/tracker.json and workspace/comms/ so it does not need you to re-paste context
• Drafts in your voice (calibrated from candidate/writing-style.md and samples in workspace/writing-samples/)
• Saves the draft to the comm record as a "ready to send" CTA on the dashboard
• Exports a .txt copy to ~/Downloads/rolester/<Company>/ or ~/Downloads/rolester/_recruiters/

Draft-only by default. Sending requires your explicit action — the skill never sends automatically.

What email-comms handles

• Reply to a recruiter message
• Follow-up after a submitted application (when there is a contact path)
• Post-interview thank-you
• Written negotiation counter-offer
• Scheduling-related prose (when schedule-meeting hands back a drafted reply)
• Cold outreach to a named contact

Scheduling (schedule-meeting)

For anything involving proposing or confirming times — "when can you talk?", "here are three slots", "can we reschedule?" — say:

schedule this / reply to these slots / set up the screen

The schedule-meeting skill:

1. Reads the proposed slots from the thread.
2. Resolves timezones clearly (the skill names every zone, never assumes).
3. Checks your availability against any calendar context you have enabled.
4. Drafts a clean availability reply and prepares a calendar-ready .ics hold.
5. Writes scheduling state back to the tracker.
6. Confirms before sending the reply or creating any calendar event.

Calendar context (optional)

If you have the calendar_read capability enabled, the skill can read free/busy from your work calendar to avoid double-booking. Without it, it drafts from the availability block in your profile (timezone + preferred hours) and degrades gracefully to draft-only + a manual .ics hold.

Calendar provider sync (calendar-sync)

To push a Rolester-tracked event into your real calendar:

add my interview with [Company] to my calendar

calendar-sync previews the exact event (time, title, notes), asks which provider (Apple Calendar, Google Calendar, Outlook), and writes only the confirmed event. It requires the calendar_sync capability to be enabled per provider.

Ingesting incoming messages

Email (ingest-mail)

# In the agent chat:
sync my email / check for new recruiter replies

The ingest-mail skill reads job-search emails from Apple Mail on macOS (or, with separate consent, Gmail/Outlook webmail) and folds recruiter replies and status changes into your tracker communications.

LinkedIn / Wellfound DMs (ingest-messages)

# In the agent chat:
sync my LinkedIn messages / check my Wellfound DMs

The ingest-messages skill reads in-platform DMs through your session browser and folds them into communications[]. Reply drafts go through email-comms. Requires the messaging capability to be enabled per platform.