outreach

name	outreach
description	Draft personalized cold outreach to a candidate the hiring manager hasn't contacted yet. Pulls background from Ashby, personalizes the hook, checks calendar for a time to propose, and sends. Use when the user says "reach out to X", "outreach to X", "email X" for a new candidate, or when sourcing passive candidates from WAAS AI Sourcer or LinkedIn.
allowed-tools	["Bash","Read","mcp__google-workspace__gmail_query_emails","mcp__google-workspace__gmail_get_email","mcp__google-workspace__calendar_get_events","mcp__claude_ai_Gmail__gmail_create_draft","mcp__gmail-drafts__gmail_send_draft","mcp__gmail-drafts__gmail_list_drafts","mcp__ashby__candidate_search","mcp__ashby__candidate_info","mcp__ashby__application_info","mcp__ashby__application_change_stage","mcp__waas__candidate_show","mcp__waas__candidate_status_show","mcp__waas__candidate_status_update","mcp__waas__candidate_messages_list","mcp__waas__candidate_message_send"]

Note: Read recruit-config/user.md for the hiring manager's name, email, and preferences. Do not hardcode any user-specific values.

Outreach — Cold Email to New Candidate

Draft personalized cold outreach to a candidate the hiring manager has never contacted. Starts a new thread.

IMPORTANT: Before drafting, read the config files:

• recruit-config/user.md — hiring manager email, Zoom link, office, Slack IDs, noise senders
• recruit-config/ashby.md — source IDs, archive reasons, email style, draft tool rules
• recruit-config/waas.md — WAAS pipeline stages, job IDs, MCP tools` — Slack/Gmail config, source IDs, archive reasons
• recruit-config/CLAUDE.local.md — Slack bot token (gitignored)
• recruit-config/jobs/product-engineer.md — outreach template, tone rules, candidate bar, Ashby job/stage IDs
• recruit-config/jobs/technical-cos.md — Technical Chief of Staff role playbook
• recruit-config/jobs/community-builder-ops-engineer.md — Community Builder and Operations Engineer role playbook
• recruit-config/jobs/design-engineer.md — Design Engineer role playbook

These files are the source of truth for all job-specific and tone details. Do not hardcode any of those values in this skill.

When to use this vs /reply

Situation	Use
Candidate has an existing email thread	/reply
New candidate, no prior contact	/outreach — this skill

Input

• /outreach Jane Doe
• /outreach John Smith, Candidate C
• "reach out to Peter Urda"
• "email Jane" (routed from /recruit when no existing thread)

Procedure

Step 1: Read config

Read all three config files to get the current template, team facts, tone rules, and Ashby IDs.

Step 2: Gather candidate background

1. Ashby: candidate_search(name) → email, company, school, position, LinkedIn, location
2. If not in Ashby: Ask the hiring manager to add them first (via Chrome Extension or WAAS export), or provide email manually
3. Check for existing threads: gmail_query_emails for any prior emails to/from this person. If a thread exists, redirect to /reply instead.

Step 3: Check calendar for a time to propose

Check the hiring manager's calendar for available 30-min slots in the next 7 business days. Find an open slot and propose it. If multiple candidates are being outreached in the same batch, stagger the proposed times.

Step 4: Personalize the hook

Write one sentence connecting the candidate's specific background to YC's work. Follow the hook pattern and tone rules from product-engineer.md.

Step 5: Draft the outreach

Use the template from the job config file (jobs/product-engineer.md). Fill in the personalized hook and proposed time. Follow all style rules from the job config.

Email formatting rule

No hard line wrapping. Write each paragraph as a single continuous line — let the email client handle wrapping. Never insert \n within a paragraph. Only use newlines between paragraphs.

Step 6: Present for approval — DO NOT SEND YET

## Outreach: {Name}
**To:** {email}
**Subject:** Reaching out from Y Combinator
**Source:** {WAAS/Applied/J&J/Chrome Extension}
**Background:** {one-line summary}
**Proposed time:** {day and time} PT

---
{draft email}
---

**d)** draft — create in Gmail drafts
**s)** send
**e)** edit — tell me what to change
**?)** something else

For multiple candidates, present all drafts first, then ask "send all?" or let the hiring manager approve one by one.

Step 7: Wait for approval

User says	Action
d	Create Gmail draft
s	Send email
e	Ask what to change, update, re-present
?	Ask the user what they want

Choosing the channel: Gmail vs WAAS messaging

Before drafting, determine the right channel:

1. Check if the candidate has a WAAS short_id — look in Ashby custom fields, or check if they came from a WAAS application email.
2. Check for existing WAAS messages via candidate_messages_list(short_id).

Situation	Channel
Candidate has WAAS short_id and no prior email thread	WAAS messaging — messages appear as emails to the candidate
Candidate is in Ashby but not WAAS (sourced via Chrome Extension, J&J, etc.)	Gmail — new thread
Candidate has both WAAS and email threads	Gmail — use the existing email thread via /reply

When using WAAS messaging:

• No draft concept — options become s/e/? (no "d")
• After sending, update WAAS status: candidate_status_update(short_id, state: "reviewing", pipeline_stage: "Reached Out")

Step 8: Execute (only after approval)

1. Send email: mcp__claude_ai_Gmail__gmail_create_draft(to, subject, body, contentType: "text/html") → gmail_send_draft(draftId)
2. Move in Ashby (if applicable): application_change_stage to "Reached Out" stage (get ID from job config)
3. Verify (MANDATORY): DO NOT report success until you have re-queried sent mail to confirm delivery. If you moved Ashby stage, check application_info to confirm. Report what you verified.

WAAS messaging channel

1. Send message: candidate_message_send(short_id, message)
2. Update WAAS stage: candidate_status_update(short_id, state: "reviewing", pipeline_stage: "Reached Out")
3. Move in Ashby (if also in Ashby): application_change_stage to "Reached Out" stage

Step 9: After sending

Report what was done:

Sent outreach to {Name} ({email}) via {Gmail/WAAS}. Proposed {day/time} PT.
Ashby: moved to Reached Out.
WAAS: moved to Reached Out.

Rules

1. NEVER send without approval. Always present first with d/s/e/? options.
2. Always personalize the hook. Never send the template verbatim without a personalized opening.
3. Always read config files first. Never hardcode team size, template, tone rules, or Ashby IDs.
4. Always propose a specific time. Check the hiring manager's calendar first.
5. Stagger times for batch outreach. Don't propose the same slot to two candidates.
6. Check for existing threads first. If there's already an email thread, use /reply instead.
7. New email, not a thread reply. This creates a new thread — no threadId.
8. Move to Reached Out in Ashby after sending (get stage ID from job config).

Gmail & Calendar Rules

• ASCII only in emails. No em dashes, curly quotes, or unicode. Use -- instead of em dashes and straight quotes. The plain-text Gmail MCP tool mangles unicode into garbage.
• Phone screen calendar invites use the title <Candidate First Name> and Ryan -- no "Phone Screen" label. Later stages (tech screen, onsite, partner) include the stage name.
• Use mcp__claude_ai_Gmail__gmail_create_draft (not mcp__gmail-drafts__gmail_create_draft) when creating email drafts. Set contentType: "text/html" and use <p> tags. The gmail-drafts tool only supports text/plain which hard-wraps lines at 78 characters, making emails look broken.
• Never create calendar invites until the candidate confirms the time. Send the outreach or scheduling email first, wait for the candidate to reply confirming, then create the calendar event. Sending an unsolicited calendar invite before confirmation is presumptuous and creates a bad impression.

Follow-Up Email Rules

When drafting follow-up emails to candidates who haven't responded to initial outreach:

Tone

• Don't say "following up," "circling back," "bumping this," "last note from me," or "I know I've tried a couple times." The recipient doesn't care about your outreach cadence. Get to the strongest lead immediately.
• No hyperbole. Don't use "exactly," "perfect fit," "ideal candidate," or superlatives about the candidate's background. Keep it grounded.
• Don't flatter. Don't say things like "exactly the depth we need" about their experience. It reads as recruiter-speak.

Content

• Follow the tone and content rules in the job playbook (recruit-config/jobs/) for role-specific framing, hooks, and what to emphasize.
• Personalize based on their background — reference specific things they've built or done, not generic bullet points.

Structure

• Two paragraphs max. First paragraph: the hook + why their background is relevant. Second paragraph: the ask.
• The call-to-action must be on its own line, separated from the body. Don't bury it in the middle of a paragraph.
• Combine the call time and coffee offer in one line: "Would Thursday at 9am or Friday at 11am work for a call? Also happy to grab coffee at our Dogpatch office if you're nearby."

Process

• Always check Gmail for prior outreach before presenting candidates as "never contacted." Search by both email and name.
• Use contentType: "text/html" when creating drafts to avoid Gmail's plain text line wrapping.

Tone Rules

• "interesting fit" not "great fit" -- softer, less presumptuous.
• "you've had experience" not "you clearly know" -- too strong.
• Don't oversell specific background matches -- keep it broader.
• Tone down academic credentials -- lead with builder/founder energy, not degrees.
• "not sure if you'd be open to it, but..." is a good soft pitch for non-obvious roles.
• "saw your profile and loved your energy" works as an opener for builder types.

Outreach Framings by Candidate Type

• Applied AI + startups: "I'm learning more about startups than I could have possibly imagined"
• Big AI company candidates (OpenAI, Meta AI): "you obviously don't need convincing on the AI front. But what I'd pitch you on is everything else."
• YC alumni/founders: "Since you already know YC from the founder side, thought it'd be worth sharing what we're building on the software team"
• Reconnects: "I might have reached out a while back, but things are moving fast here and wanted to reconnect" (say "might have" not "definitely did")
• Non-traditional backgrounds: "We're looking for people with non-traditional backgrounds who can think across disciplines and build"
• YC as learning org: "At its core, YC is a learning organization -- we teach founders how to build companies"
• Unlimited AI tokens as a consistent selling point across all candidate types.
• Multi-role pitches: Frequently pitch 2 roles in one email (PE + Technical CoS, or Community Builder + Technical CoS) -- works well for versatile candidates.

Follow-up Cadence

• First outreach: personalized, reference their background
• Follow-up (7 days): shorter, personalized nudge, suggest specific time (Thursday AM)
• Last nudge (14+ days): very short, "last nudge from me", no pressure, just drop Zoom link
• After 2 follow-ups with no reply: archive in Ashby, reactivate if they reply later

Fraud Detection

Watch for these signals in Ashby applications:

• LinkedIn URL is broken or just a few characters (e.g., /in/c)
• Unusual LinkedIn slug patterns
• Phone area code doesn't match claimed location
• Check Ashby's fraudStatus field if available in the UI
• Multiple candidates with identical IP addresses or user agents