ten31-database/backend/mcp/outreach_agent.py

"""Outreach drafting agent — tailored LP outreach in Ten31's voice, grounded in the
thesis + the LP's DE-IDENTIFIED context, through the redaction boundary.

Draft-only: a human reviews, edits, and sends (guardrails #4 and #6 — no auto-send,
no cold/outbound automation until counsel defines the solicitation posture). Sovereignty:
the thesis is Ten31's own non-sensitive messaging and goes to Claude as-is; the LP's
context (CRM notes + email history) is scrubbed first, so the LP list never reaches the
API in the clear, and the draft is re-hydrated locally for the human.
"""
import json
import os
import sys

_HERE = os.path.dirname(os.path.abspath(__file__))

# outreach_type -> human description woven into the prompt
OUTREACH_TYPES = {
    "intro": "a first introduction to Ten31 and the fund",
    "follow_up": "a warm follow-up that moves the conversation forward",
    "fund_update": "a fund update / progress note",
    "meeting_follow_up": "a follow-up after a recent meeting or call",
    "nurture": "a light-touch note to stay in contact",
}


def _days_between(then_iso, now_iso):
    from datetime import datetime
    try:
        a = datetime.strptime(str(then_iso)[:10], "%Y-%m-%d")
        b = datetime.strptime(str(now_iso)[:10], "%Y-%m-%d")
        return (b - a).days
    except Exception:
        return None


def follow_up_radar(conn, our_addresses, now_iso, warm_days=45, limit=60):
    """Deterministic scan: surface investors who need attention, each with a concrete,
    checkable reason (no LLM guesswork in the *surfacing*). Tiers, most urgent first:
      0  you owe a reply (their email is the most recent, unanswered)
      1  flagged for follow-up and quiet
      2  warm lead gone quiet (no contact in >= warm_days)
    """
    own = {(a or "").lower() for a in (our_addresses or [])}
    try:
        rows = conn.execute("SELECT * FROM fundraising_investors").fetchall()
    except Exception:
        return []
    items = []
    for r in rows:
        d = dict(r)
        inv_id, name = d.get("id"), d.get("investor_name")
        if not inv_id:
            continue
        gv = d.get("graveyard")
        if gv and str(gv).strip().lower() not in ("", "0", "false", "no"):
            continue  # buried leads are out of scope
        try:
            erows = conn.execute(
                "SELECT e.from_email, e.sent_at FROM emails e "
                "JOIN email_investor_links l ON l.email_id = e.id "
                "WHERE l.fundraising_investor_id = ? AND e.is_matched = 1 "
                "ORDER BY e.sent_at DESC LIMIT 50", (inv_id,)).fetchall()
        except Exception:
            erows = []
        if not erows:
            continue  # no email history -> nothing to base a nudge on
        last = erows[0]
        days = _days_between(last["sent_at"], now_iso)
        if days is None:
            continue
        inbound_last = (last["from_email"] or "").lower() not in own  # they emailed last
        ff = d.get("follow_up")
        flagged = bool(ff) and str(ff).strip().lower() not in ("", "0", "false", "no")

        reason, tier, suggested = None, None, "follow_up"
        if inbound_last and days >= 3:
            reason, tier, suggested = f"You owe a reply — they emailed {days} days ago", 0, "follow_up"
        elif flagged and days >= 14:
            reason, tier, suggested = f"Flagged for follow-up, quiet {days} days", 1, "follow_up"
        elif days >= warm_days and len(erows) >= 2:
            reason, tier, suggested = f"No contact in {days} days", 2, "nurture"
        if reason is None:
            continue
        if flagged and tier != 1:
            reason += " · flagged"
        items.append({"investor_id": inv_id, "name": name, "reason": reason,
                      "days_since": days, "suggested_type": suggested, "tier": tier})
    items.sort(key=lambda x: (x["tier"], -x["days_since"]))
    return items[:limit]


def _context(conn, investor_id):
    """Assemble the recipient's context. Structured so the model replies to the ACTIVE
    conversation (the most recent email thread) while still having earlier emails as
    background. Returns (investor_name, context_text) or (None, None)."""
    row = conn.execute("SELECT investor_name, notes FROM fundraising_investors WHERE id=?",
                       (investor_id,)).fetchone()
    if not row:
        return None, None
    name = row["investor_name"]
    header = [f"Investor: {name}"]
    notes = (row["notes"] or "").strip()
    if notes:
        header.append("CRM notes:\n" + notes)
    try:
        rows = conn.execute(
            "SELECT e.subject, e.body_text, e.snippet, e.sent_at, e.thread_id FROM emails e "
            "JOIN email_investor_links l ON l.email_id = e.id "
            "WHERE l.fundraising_investor_id = ? AND e.is_matched = 1 "
            "ORDER BY e.sent_at DESC LIMIT 20", (investor_id,)).fetchall()
    except Exception:
        rows = []  # email tables may be absent / not yet captured
    active, background = [], []
    if rows:
        active_thread = rows[0]["thread_id"]
        for em in rows:
            body = (em["body_text"] or em["snippet"] or "")[:1500].strip()
            block = f"({(em['sent_at'] or '')[:10]}) {em['subject'] or '(no subject)'}\n{body}"
            in_active = active_thread is not None and em["thread_id"] == active_thread
            (active if in_active else background).append(block)
    sections = ["\n".join(header)]
    if active:
        sections.append("=== Active conversation (the most recent thread — this is what you are replying to) ===\n"
                        + "\n\n".join(reversed(active[:6])))
    if background:
        sections.append("=== Earlier emails (background only, not the active thread) ===\n"
                        + "\n\n".join(background[:4]))
    return name, "\n\n".join(sections)


# Keyword cues used to pick the sender's prior emails of the SAME PURPOSE as the draft
# (so the voice few-shot matches what they're writing, not just whatever is most recent).
PURPOSE_PATTERNS = {
    "intro": ["introduc", "nice to meet", "reaching out", "wanted to connect", "by way of introduction", "e-meet"],
    "follow_up": ["follow up", "following up", "circle back", "circling back", "checking in",
                  "wanted to revisit", "any thoughts", "wanted to follow", "touching base"],
    "fund_update": ["update", "progress", "quarter", "deployed", "portfolio", "milestone", "closing", "fund iii"],
    "meeting_follow_up": ["great to meet", "great speaking", "thanks for the call", "thanks for your time",
                          "after our", "following our", "enjoyed our", "great to connect", "great chatting"],
    "nurture": ["checking in", "hope you", "thinking of you", "stay in touch", "wanted to share", "thought you"],
}


def _voice_examples(conn, sender_email, outreach_type=None, limit=8):
    """The sender's OWN sent LP emails OF THE SAME PURPOSE — used as voice few-shot AND
    surfaced for transparency (no black box). Larger sample, purpose-weighted (not just
    recent). Returns (blocks_for_model, meta_for_ui); meta is the sender's own emails."""
    if not sender_email:
        return [], []
    try:
        rows = conn.execute(
            "SELECT subject, body_text, snippet, sent_at, to_emails_json FROM emails "
            "WHERE LOWER(from_email) = LOWER(?) AND is_matched = 1 "
            "AND body_text IS NOT NULL AND TRIM(body_text) <> '' "
            "ORDER BY sent_at DESC LIMIT 80", (sender_email,)).fetchall()
    except Exception:
        return [], []
    pats = PURPOSE_PATTERNS.get(outreach_type or "", [])
    scored = []
    for idx, r in enumerate(rows):
        text = ((r["subject"] or "") + " " + (r["body_text"] or r["snippet"] or "")).lower()
        score = sum(1 for p in pats if p in text)
        scored.append((score, -idx, r))  # purpose match first, then more recent
    scored.sort(key=lambda x: (x[0], x[1]), reverse=True)
    blocks, meta = [], []
    for score, _neg_idx, r in scored[:limit]:
        body = (r["body_text"] or r["snippet"] or "")[:900].strip()
        if not body:
            continue
        blocks.append(f"Example — {r['subject'] or '(no subject)'}\n{body}")
        to = ""
        try:
            arr = json.loads(r["to_emails_json"] or "[]")
            if arr:
                to = arr[0].get("email") if isinstance(arr[0], dict) else arr[0]
        except Exception:
            to = ""
        meta.append({"subject": r["subject"] or "(no subject)", "date": (r["sent_at"] or "")[:10],
                     "to": to, "on_topic": score > 0})
    return blocks, meta


def _draft_with_claude(aa, thesis, type_desc, deident_context, deident_voice, guidance):
    voice_block = ""
    if deident_voice:
        voice_block = ("\n\nHere are examples of how THIS sender actually writes (de-identified). Match their "
                       "voice, tone, sentence rhythm, openers, and sign-off — not just the rules above:\n\n"
                       + "\n\n---\n\n".join(deident_voice))
    system = (
        "You are Ten31's outreach copilot. Draft ONE ready-to-send LP outreach email in the SENDER's voice. "
        f"VOICE RULES (follow exactly): {aa.VOICE}" + voice_block + "\n\n"
        "Ten31 invests in critical infrastructure across bitcoin, AI, energy, and freedom technologies. "
        "The spine: fiat is being debased while AI drives the marginal cost of the reproducible toward "
        "zero, so durable value accrues to what stays provably scarce, and the monetary premium accrues "
        "to bitcoin as the apex non-debasable reserve asset. AI is the abundance engine and bitcoin is "
        "the scarcity anchor. Ten31 owns the scarce links of that one supply chain. This is an "
        "asset-value and capital-flow conviction, not a claim that the world transacts or settles in "
        "bitcoin. Current working thesis:\n" + aa._render_thesis(thesis) + "\n\n"
        "The recipient's context below is DE-IDENTIFIED: people, firms, and amounts appear as placeholders "
        "like [PERSON_1], [ORG_1], [AMOUNT_1]. Keep every placeholder EXACTLY as written and NEVER invent new "
        "ones — they are swapped back to real values after you reply. Reply to the ACTIVE conversation; use the "
        "earlier emails only as background. Output a subject line, then the email body. Do NOT fabricate facts, "
        "numbers, returns, or commitments that are not present in the context or the thesis.")
    user = (f"Outreach type: {type_desc}\n\n"
            f"Recipient context (de-identified):\n{deident_context}\n\n"
            + (f"Additional guidance from the sender: {guidance}\n\n" if (guidance or "").strip() else "")
            + "Draft the email now.")
    resp = aa._client().messages.create(
        model=aa.MODEL, max_tokens=1200,
        system=[{"type": "text", "text": system, "cache_control": {"type": "ephemeral"}}],
        messages=[{"role": "user", "content": user}])
    return "".join(b.text for b in resp.content if getattr(b, "type", None) == "text")


def draft_outreach(conn, investor_id, outreach_type, guidance, db_path, sender_email=None):
    """Draft tailored outreach for one investor, in the SENDER's voice (few-shot from
    their own prior emails). FAILS CLOSED: if the scrub can't be prepared or Claude
    hallucinates a placeholder, no de-anonymized draft is returned."""
    name, context = _context(conn, investor_id)
    if not name:
        return {"status": "not_found"}
    type_desc = OUTREACH_TYPES.get(outreach_type, OUTREACH_TYPES["follow_up"])
    voice_blocks, voice_meta = _voice_examples(conn, sender_email, outreach_type)

    # 1) Scrub the sender's voice examples + the recipient context TOGETHER (shared token
    #    space). Nothing reaches Claude in the clear; the voice examples are reference only.
    try:
        sys.path.insert(0, os.path.dirname(_HERE))  # backend/ for the redaction package
        from redaction.client import Boundary
        boundary = Boundary(db_path=db_path, actor="closer")
        scrubbed = boundary.scrub(list(voice_blocks) + [context], bucket=False, conn=conn)
    except Exception as exc:
        return {"status": "scrub_unavailable", "reason": str(exc)}
    items = scrubbed["items"]
    deident_voice, deident_target = items[:-1], items[-1]
    handle = scrubbed["handle"]

    # 2) Claude drafts over the de-identified context + voice + (non-sensitive) thesis.
    try:
        sys.path.insert(0, _HERE)
        import architect_agent as aa
        thesis = aa.at.get_thesis("core", db=db_path)
        raw = _draft_with_claude(aa, thesis, type_desc, deident_target, deident_voice, guidance)
    except Exception as exc:
        boundary.forget(handle)
        return {"status": "claude_not_configured", "reason": str(exc)}

    # 3) Re-hydrate locally (strict: a hallucinated placeholder quarantines the draft).
    rehy = boundary.rehydrate(raw, handle, strict=True, conn=conn)
    boundary.forget(handle)
    if rehy.get("error"):
        return {"status": "rehydrate_failed"}
    return {"status": "ok", "draft": rehy["text"], "investor_name": name,
            "scrub_stats": scrubbed.get("stats", {}), "voice_examples": voice_meta}