outreach: follow-up radar — deterministic "needs attention" + one-click draft (v0.1.0:69)

The Outreach page now opens with a "Needs attention" list. A deterministic scan
(outreach_agent.follow_up_radar) surfaces investors per the email history: tier 0 "you
owe a reply" (their email is the most recent, unanswered, >=3d), tier 1 flagged + quiet,
tier 2 warm lead gone quiet (no contact in >=45d). Most urgent first; every reason is
verifiable from the data (no LLM in the surfacing — the deliberate fix for the trust
problem that sank objection-grounding). Excludes graveyard; needs email history. One
click sets the investor + suggested type (follow-up/nurture) and runs the existing
outreach drafter. Route GET /api/outreach/radar. Test mcp/test_outreach.py extended
(owe-reply/warm-quiet/recent/graveyard/order). Verified live in preview.

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

backend/mcp/outreach_agent.py

@@ -22,6 +22,72 @@ OUTREACH_TYPES = {
 }
 
 
+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: CRM notes + recent matched email with them.
     Returns (investor_name, context_text) or (None, None)."""

backend/mcp/test_outreach.py

@@ -55,6 +55,43 @@ def main():
     check(set(["intro", "follow_up", "fund_update", "meeting_follow_up", "nurture"]) <= set(oa.OUTREACH_TYPES),
           "outreach types catalogue present")
 
+    # ── follow-up radar ──
+    rc = sqlite3.connect(os.path.join(tempfile.mkdtemp(), "radar.db"))
+    rc.row_factory = sqlite3.Row
+    rc.executescript("""
+        CREATE TABLE fundraising_investors (id TEXT PRIMARY KEY, investor_name TEXT, follow_up TEXT, graveyard TEXT);
+        CREATE TABLE emails (id TEXT PRIMARY KEY, from_email TEXT, sent_at TEXT, is_matched INT);
+        CREATE TABLE email_investor_links (id TEXT, email_id TEXT, fundraising_investor_id TEXT);
+    """)
+    rc.executemany("INSERT INTO fundraising_investors (id,investor_name,follow_up,graveyard) VALUES (?,?,?,?)", [
+        ("owe", "Owe Reply LP", None, None),     # they emailed last, 5d ago -> tier 0
+        ("warm", "Warm Quiet LP", None, None),   # we emailed last, 60d ago -> tier 2
+        ("fresh", "Fresh LP", None, None),       # we emailed 4d ago -> not surfaced
+        ("buried", "Buried LP", None, "1"),      # graveyard -> excluded
+    ])
+    OURS = "grant@ten31.xyz"
+    em = [
+        ("o1", "lp@owe.example", "2026-06-04T10:00:00", "owe"),     # inbound, 5 days before 06-09
+        ("w1", OURS, "2026-04-10T10:00:00", "warm"),                # outbound, ~60 days
+        ("w0", "lp@warm.example", "2026-04-01T10:00:00", "warm"),   # 2nd email for history
+        ("f1", OURS, "2026-06-05T10:00:00", "fresh"),               # outbound, 4 days -> too recent
+        ("b1", "lp@buried.example", "2026-01-01T10:00:00", "buried"),
+    ]
+    for eid, frm, sent, inv in em:
+        rc.execute("INSERT INTO emails (id,from_email,sent_at,is_matched) VALUES (?,?,?,1)", (eid, frm, sent))
+        rc.execute("INSERT INTO email_investor_links (id,email_id,fundraising_investor_id) VALUES (?,?,?)", (eid + "l", eid, inv))
+    rc.commit()
+    radar = oa.follow_up_radar(rc, [OURS], "2026-06-09T00:00:00", warm_days=45)
+    names = [x["name"] for x in radar]
+    check("Owe Reply LP" in names and "Warm Quiet LP" in names, f"surfaces owe-reply + warm-quiet (got {names})")
+    check("Fresh LP" not in names, "recent contact not surfaced")
+    check("Buried LP" not in names, "graveyard excluded")
+    check(radar[0]["name"] == "Owe Reply LP" and radar[0]["tier"] == 0, "owe-a-reply ranked first (tier 0)")
+    owe = next(x for x in radar if x["name"] == "Owe Reply LP")
+    check("owe a reply" in owe["reason"] and owe["suggested_type"] == "follow_up", "owe-reply reason + suggested type")
+    warm = next(x for x in radar if x["name"] == "Warm Quiet LP")
+    check(warm["tier"] == 2 and warm["suggested_type"] == "nurture", "warm-quiet is tier 2, suggests nurture")
+
     if FAILS:
         print(f"\nFAILED ({len(FAILS)})")
         for f in FAILS:

backend/server.py

@@ -1808,6 +1808,8 @@ class CRMHandler(BaseHTTPRequestHandler):
             return self.handle_list_activity_proposals(user)
         if path == '/api/outreach/investors':
             return self.handle_list_outreach_investors(user)
+        if path == '/api/outreach/radar':
+            return self.handle_outreach_radar(user)
 
         # Users
         if path == '/api/users':
@@ -3920,6 +3922,21 @@ class CRMHandler(BaseHTTPRequestHandler):
         finally:
             conn.close()
 
+    def handle_outreach_radar(self, user):
+        """Deterministic 'who needs attention' scan (reasons are checkable, not LLM guesses)."""
+        if _outreach_agent is None:
+            return self.send_error_json("Outreach agent unavailable", 503)
+        conn = get_db()
+        try:
+            try:
+                own = [r[0] for r in conn.execute("SELECT email_address FROM email_accounts")]
+            except Exception:
+                own = []
+            items = _outreach_agent.follow_up_radar(conn, own, now())
+            return self.send_json({"items": items})
+        finally:
+            conn.close()
+
     def handle_outreach_draft(self, user, body):
         """Draft tailored LP outreach through the redaction boundary (draft-only —
         a human reviews/edits/sends; guardrails #4, #6)."""

frontend/index.html

@@ -9956,6 +9956,7 @@
             const [drafting, setDrafting] = useState(false);
             const [result, setResult] = useState(null);
             const [draftText, setDraftText] = useState('');
+            const [radar, setRadar] = useState([]);
             const TYPES = [
                 ['intro', 'Intro'],
                 ['follow_up', 'Warm follow-up'],
@@ -9977,19 +9978,25 @@
                         const r = await api('/api/outreach/investors', {}, token);
                         if (!cancelled) setInvestors(Array.isArray(r?.investors) ? r.investors : []);
                     } catch (_) { /* none */ }
+                    try {
+                        const rr = await api('/api/outreach/radar', {}, token);
+                        if (!cancelled) setRadar(Array.isArray(rr?.items) ? rr.items : []);
+                    } catch (_) { /* none */ }
                 })();
                 return () => { cancelled = true; };
             }, [token]);
 
-            const draft = async () => {
+            const draft = async (ovInvestor, ovType) => {
                 if (drafting) return;
-                if (!investorId) { onShowToast('Pick an investor first', 'error'); return; }
+                const inv = ovInvestor || investorId;
+                const t = ovType || type;
+                if (!inv) { onShowToast('Pick an investor first', 'error'); return; }
                 try {
                     setDrafting(true);
                     setResult(null);
                     const res = await api('/api/outreach/draft', {
                         method: 'POST',
-                        body: JSON.stringify({ investor_id: investorId, outreach_type: type, guidance }),
+                        body: JSON.stringify({ investor_id: inv, outreach_type: t, guidance }),
                     }, token);
                     const data = res.data || res;
                     setResult(data);
@@ -10013,6 +10020,33 @@
             return (
                 <div className="page-container">
                     <h2 className="section-title" style={{ marginBottom: '20px' }}>Outreach</h2>
+
+                    {radar.length > 0 && (
+                        <div className="section">
+                            <div className="section-title" style={{ display: 'flex', alignItems: 'center', gap: '8px' }}>
+                                Needs attention
+                                <span className="approval-pill">{radar.length}</span>
+                            </div>
+                            <div className="index-action-hint" style={{ marginTop: 0, marginBottom: '12px' }}>
+                                Investors who are waiting on a reply or have gone quiet, most urgent first. Every reason is verifiable from your email history — no guesswork. Click Draft to compose in your voice.
+                            </div>
+                            {radar.map((it) => (
+                                <div key={it.investor_id} className="merge-candidate-card"
+                                    style={{ display: 'flex', justifyContent: 'space-between', alignItems: 'center', gap: '12px', marginBottom: '8px' }}>
+                                    <div>
+                                        <div style={{ fontWeight: 600 }}>{it.name}</div>
+                                        <div className="kpi-subtitle">{it.reason}</div>
+                                    </div>
+                                    <button
+                                        onClick={() => { setInvestorId(it.investor_id); setType(it.suggested_type); draft(it.investor_id, it.suggested_type); }}
+                                        disabled={drafting}>
+                                        {drafting ? '…' : `Draft ${it.suggested_type === 'nurture' ? 'nurture' : 'follow-up'}`}
+                                    </button>
+                                </div>
+                            ))}
+                        </div>
+                    )}
+
                     <div className="section">
                         <div className="index-action-hint" style={{ marginTop: 0, marginBottom: '12px' }}>
                             Drafts a tailored LP email in Ten31's voice, grounded in the thesis and that investor's CRM notes + email history. The investor's details are de-identified before Claude sees them and restored locally, so the LP list never leaves Ten31. Drafts only — you review, edit, and send.

start9/0.4/startos/utils.ts

@@ -33,8 +33,9 @@ export const PACKAGE_TITLE = 'Ten31 Database'
 //   * 0.1.0:65 (Email Capture: per-mailbox captured/matched counts)
 //   * 0.1.0:66 (LP Objections page: UI trigger for the Architect grounding pass)
 //   * 0.1.0:67 (remove LP Objections page — generic/unverifiable; pivot to proactive outreach)
-//   * Current:        0.1.0:68 (Outreach Draft Assistant — tailored LP drafts via thesis + redaction boundary)
+//   * 0.1.0:68 (Outreach Draft Assistant — tailored LP drafts via thesis + redaction boundary)
-export const PACKAGE_VERSION = '0.1.0:68'
+//   * Current:        0.1.0:69 (follow-up radar — deterministic "needs attention" list + one-click draft)
+export const PACKAGE_VERSION = '0.1.0:69'
 
 export const DATA_MOUNT_PATH = '/data'
 export const WEB_PORT = 8080

start9/0.4/startos/versions/index.ts

@@ -29,8 +29,9 @@ import { v_0_1_0_65 } from './v0.1.0.65'
 import { v_0_1_0_66 } from './v0.1.0.66'
 import { v_0_1_0_67 } from './v0.1.0.67'
 import { v_0_1_0_68 } from './v0.1.0.68'
+import { v_0_1_0_69 } from './v0.1.0.69'
 
 export const versionGraph = VersionGraph.of({
-  current: v_0_1_0_68,
+  current: v_0_1_0_69,
-  other: [v_0_1_0_39, v_0_1_0_40, v_0_1_0_41, v_0_1_0_42, v_0_1_0_43, v_0_1_0_44, v_0_1_0_45, v_0_1_0_46, v_0_1_0_47, v_0_1_0_48, v_0_1_0_49, v_0_1_0_50, v_0_1_0_51, v_0_1_0_52, v_0_1_0_53, v_0_1_0_54, v_0_1_0_55, v_0_1_0_56, v_0_1_0_57, v_0_1_0_58, v_0_1_0_59, v_0_1_0_60, v_0_1_0_61, v_0_1_0_62, v_0_1_0_63, v_0_1_0_64, v_0_1_0_65, v_0_1_0_66, v_0_1_0_67],
+  other: [v_0_1_0_39, v_0_1_0_40, v_0_1_0_41, v_0_1_0_42, v_0_1_0_43, v_0_1_0_44, v_0_1_0_45, v_0_1_0_46, v_0_1_0_47, v_0_1_0_48, v_0_1_0_49, v_0_1_0_50, v_0_1_0_51, v_0_1_0_52, v_0_1_0_53, v_0_1_0_54, v_0_1_0_55, v_0_1_0_56, v_0_1_0_57, v_0_1_0_58, v_0_1_0_59, v_0_1_0_60, v_0_1_0_61, v_0_1_0_62, v_0_1_0_63, v_0_1_0_64, v_0_1_0_65, v_0_1_0_66, v_0_1_0_67, v_0_1_0_68],
 })

start9/0.4/startos/versions/v0.1.0.69.ts

@@ -0,0 +1,18 @@
+import { VersionInfo } from '@start9labs/start-sdk'
+
+// Follow-up radar on the Outreach page. A deterministic scan surfaces investors who
+// need attention — "you owe a reply" (their email is unanswered), or a warm lead gone
+// quiet (no contact in 45+ days) — most urgent first, each with a checkable reason from
+// the email history (no LLM guesswork in the surfacing). One click drafts the suggested
+// follow-up/nurture in your voice via the existing outreach drafter. No schema change.
+export const v_0_1_0_69 = VersionInfo.of({
+  version: '0.1.0:69',
+  releaseNotes: {
+    en_US: [
+      'Outreach now opens with a "Needs attention" list: investors waiting on a reply or gone',
+      'quiet (45+ days), most urgent first, each with a reason you can verify from the email',
+      'history. One click drafts the right follow-up or nurture in your voice.',
+    ].join(' '),
+  },
+  migrations: { up: async () => {}, down: async () => {} },
+})