outreach: Outreach Draft Assistant — tailored LP drafts (v0.1.0:68)

First proactive-messaging build. New "Outreach" page (all authenticated users): pick an
investor + type (intro / follow-up / fund update / meeting follow-up / nurture) + optional
guidance; the agent drafts a tailored LP email in Ten31's voice, grounded in the thesis +
that investor's CRM notes and matched email history. The draft is editable + copyable;
nothing is sent (draft-only — guardrails #4, #6).

Sovereignty: the thesis is Ten31's own non-sensitive messaging (to Claude as-is); the LP
context is scrubbed through the redaction boundary before Claude, drafted with placeholders,
and re-hydrated locally — the LP list never reaches the API. Fails closed (scrub_unavailable /
claude_not_configured / rehydrate_failed quarantines a hallucinated-token draft).

Backend: mcp/outreach_agent.py (context assembly + scrub + Claude + rehydrate, reusing
architect_agent's client/thesis/voice + the Boundary); routes GET /api/outreach/investors,
POST /api/outreach/draft; logged. Test mcp/test_outreach.py (context assembly). Verified in
preview: page/selector/types/guidance render, fail-closed at the key-less Claude step (scrub
ran locally first), success rendering verified with a mocked ok draft.

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

backend/mcp/test_outreach.py

@@ -0,0 +1,67 @@
+#!/usr/bin/env python3
+"""Test the outreach agent's context assembly: it pulls the investor's CRM notes +
+recent matched email into the de-identifiable context block. Synthetic data only
+(guardrail #9). The scrub/Claude/rehydrate round-trip is exercised live in the preview.
+Run: cd backend && python3 mcp/test_outreach.py
+"""
+import os
+import sqlite3
+import sys
+import tempfile
+
+sys.path.insert(0, os.path.dirname(os.path.abspath(__file__)))
+import outreach_agent as oa  # noqa: E402
+
+FAILS = []
+
+
+def check(cond, msg):
+    print(("  PASS " if cond else "  FAIL ") + msg)
+    if not cond:
+        FAILS.append(msg)
+
+
+def main():
+    db = os.path.join(tempfile.mkdtemp(), "t.db")
+    c = sqlite3.connect(db)
+    c.row_factory = sqlite3.Row
+    c.executescript("""
+        CREATE TABLE fundraising_investors (id TEXT PRIMARY KEY, investor_name TEXT, notes TEXT);
+        CREATE TABLE emails (id TEXT PRIMARY KEY, subject TEXT, body_text TEXT, snippet TEXT, sent_at TEXT, is_matched INT);
+        CREATE TABLE email_investor_links (id TEXT, email_id TEXT, fundraising_investor_id TEXT);
+    """)
+    c.execute("INSERT INTO fundraising_investors VALUES ('inv1','Harbor & Vine','Met at the conference; interested in Fund III.')")
+    c.executemany("INSERT INTO emails (id,subject,body_text,sent_at,is_matched) VALUES (?,?,?,?,1)", [
+        ("e1", "Re: Fund III", "Thanks for the call. We are still weighing the lock-up terms.", "2026-06-02T10:00:00"),
+        ("e2", "Intro", "Good to meet you at the dinner.", "2026-05-01T10:00:00"),
+        ("e3", "Spam", "ignore me", "2026-04-01T10:00:00"),  # not linked -> excluded
+    ])
+    c.executemany("INSERT INTO email_investor_links (id,email_id,fundraising_investor_id) VALUES (?,?, 'inv1')",
+                  [("l1", "e1"), ("l2", "e2")])
+    c.commit()
+
+    name, ctx = oa._context(c, "inv1")
+    check(name == "Harbor & Vine", f"resolves investor name (got {name!r})")
+    check("Met at the conference" in ctx, "includes CRM notes")
+    check("lock-up terms" in ctx, "includes matched email body")
+    check("Good to meet you" in ctx, "includes a second matched email")
+    check("ignore me" not in ctx, "excludes email not linked to this investor")
+    check(ctx.index("lock-up terms") < ctx.index("Good to meet you"), "newest email first")
+
+    n2, c2 = oa._context(c, "missing")
+    check(n2 is None and c2 is None, "unknown investor -> (None, None)")
+
+    # type catalogue is intact
+    check(set(["intro", "follow_up", "fund_update", "meeting_follow_up", "nurture"]) <= set(oa.OUTREACH_TYPES),
+          "outreach types catalogue present")
+
+    if FAILS:
+        print(f"\nFAILED ({len(FAILS)})")
+        for f in FAILS:
+            print("  - " + f)
+        sys.exit(1)
+    print("\nALL PASS (outreach context assembly)")
+
+
+if __name__ == "__main__":
+    main()