refactor(agents): share leadership role detector, use word-boundary match

P2-23: 'lead' in system-prompt.ts matched 'cleaner' / 'leaderboard' via
substring .includes(). Hoist LEADERSHIP_ROLE_KEYWORDS into a shared
agent-role-helpers.ts module; tokenize input on non-alphanum to require
whole-word match.

P3-54: Same keyword list was duplicated in automation-skills with drift
(missing 'ceo', different members). Both sites now call through the
shared helper.

src/main/agent-role-helpers.ts

@@ -0,0 +1,33 @@
+/**
+ * Role-classification helpers used across prompt construction and skill
+ * auto-assignment. Keeping a single keyword list here prevents drift
+ * between system-prompt.ts and automation-skills.ts.
+ *
+ * Matching uses word-boundary tokenization instead of substring search,
+ * so "lead" does not match "cleaner" or "leaderboard".
+ */
+
+export const LEADERSHIP_ROLE_KEYWORDS = [
+  "chief",
+  "cto",
+  "cmo",
+  "coo",
+  "cfo",
+  "ceo",
+  "vp",
+  "vice",
+  "president",
+  "head",
+  "director",
+  "manager",
+  "lead",
+] as const;
+
+function tokenize(text: string): string[] {
+  return text.toLowerCase().match(/[a-z0-9]+/g) ?? [];
+}
+
+export function roleMatchesLeadershipKeywords(role: string, title?: string | null): boolean {
+  const tokens = new Set(tokenize(`${role} ${title ?? ""}`));
+  return LEADERSHIP_ROLE_KEYWORDS.some((keyword) => tokens.has(keyword));
+}

src/main/api-server/routes-files.ts

@@ -294,7 +294,8 @@ export function registerFileRoutes(server: AgentApiServer) {
     if (!wpId) { server.json(res, 400, { error: "Missing workProductId" }); return; }
     const parsed = updateWorkProductSchema.safeParse(body);
     if (!parsed.success) { server.json(res, 400, { error: "Invalid input", details: parsed.error.flatten() }); return; }
-    db.updateWorkProduct(wpId, token.companyId, parsed.data);
+    const changes = db.updateWorkProduct(wpId, token.companyId, parsed.data);
+    if (changes === 0) { server.json(res, 404, { error: "Work product not found" }); return; }
     onDomainChanged();
     server.json(res, 200, { updated: true });
   });
@@ -302,7 +303,8 @@ export function registerFileRoutes(server: AgentApiServer) {
   server.addRoute("DELETE", "/api/work-products/:workProductId", (_req, res, params, token) => {
     const wpId = params.workProductId;
     if (!wpId) { server.json(res, 400, { error: "Missing workProductId" }); return; }
-    db.deleteWorkProduct(wpId, token.companyId);
+    const changes = db.deleteWorkProduct(wpId, token.companyId);
+    if (changes === 0) { server.json(res, 404, { error: "Work product not found" }); return; }
     onDomainChanged();
     server.json(res, 200, { deleted: true });
   });

src/main/automation/automation-skills.ts

@@ -1,4 +1,5 @@
 import type { AppDatabase } from "../database";
+import { roleMatchesLeadershipKeywords } from "../agent-role-helpers";
 
 const DEPARTMENT_SKILL_KEYWORDS: Record<string, string[]> = {
   engineering: ["code", "engineer", "develop", "program", "software", "api", "backend", "frontend", "full-stack", "fullstack", "devops", "infrastructure", "system", "architect", "debug", "test", "ci", "cd", "deploy", "docker", "kubernetes", "database", "sql", "git", "typescript", "javascript", "python", "rust", "go", "java", "react", "node", "css", "html", "web"],
@@ -52,10 +53,10 @@ function scoreSkillAgentMatch(
     }
   }
 
-  // Executives need awareness of all domains
-  const executiveRoles = ["ceo", "cto", "coo", "cfo", "cmo", "vp", "chief", "director", "head", "lead"];
-  const roleLower = agent.role.toLowerCase();
-  if (executiveRoles.some((r) => roleLower.includes(r))) {
+  // Executives need awareness of all domains. Use the shared leadership
+  // keyword list with word-boundary matching so "lead" does not match
+  // "cleaner" / "leaderboard" in agent role strings.
+  if (roleMatchesLeadershipKeywords(agent.role, agent.title)) {
     score += 1;
   }
 

src/main/database.ts

@@ -93,9 +93,9 @@ export class AppDatabase extends AppDatabaseBase {
   getDocumentLatestRevisionId(documentId: string) { return this.documentsMod.getDocumentLatestRevisionId(documentId); }
   listDocumentRevisions(documentId: string, companyId: string) { return this.documentsMod.listDocumentRevisions(documentId, companyId); }
   createWorkProduct(input: { companyId: string; taskId: string; projectId?: string | null; type: string; provider: string; externalId?: string | null; title: string; url?: string | null; status?: string; reviewState?: string; isPrimary?: boolean; summary?: string | null; metadataJson?: string | null; createdByRunId?: string | null }) { return this.documentsMod.createWorkProduct(input); }
-  updateWorkProduct(id: string, companyId: string, patch: Record<string, unknown>) { this.documentsMod.updateWorkProduct(id, companyId, patch); }
+  updateWorkProduct(id: string, companyId: string, patch: Parameters<ReturnType<typeof import("./database/documents").buildDocumentMethods>["updateWorkProduct"]>[2]) { return this.documentsMod.updateWorkProduct(id, companyId, patch); }
   listWorkProductsForTask(taskId: string, companyId: string) { return this.documentsMod.listWorkProductsForTask(taskId, companyId); }
-  deleteWorkProduct(id: string, companyId: string) { this.documentsMod.deleteWorkProduct(id, companyId); }
+  deleteWorkProduct(id: string, companyId: string) { return this.documentsMod.deleteWorkProduct(id, companyId); }
   linkDocumentToTask(taskId: string, documentId: string, companyId: string, key: string) { return this.documentsMod.linkDocumentToTask(taskId, documentId, companyId, key); }
   unlinkDocumentFromTask(taskId: string, key: string, companyId: string) { this.documentsMod.unlinkDocumentFromTask(taskId, key, companyId); }
   listDocumentsForTask(taskId: string, companyId: string) { return this.documentsMod.listDocumentsForTask(taskId, companyId); }

src/main/database/documents.ts

@@ -211,20 +211,48 @@ export function buildDocumentMethods(
       return id;
     },
 
-    updateWorkProduct(id: string, companyId: string, patch: Record<string, unknown>): void {
+    updateWorkProduct(
+      id: string,
+      companyId: string,
+      patch: {
+        type?: string;
+        provider?: string;
+        externalId?: string | null;
+        title?: string;
+        url?: string | null;
+        status?: string;
+        reviewState?: string;
+        isPrimary?: boolean;
+        summary?: string | null;
+        metadataJson?: string | null;
+      },
+    ): number {
       const ts = nowIso();
       const sets: string[] = ["updated_at = ?"];
-      const values: unknown[] = [ts];
-      const ALLOWED = new Set(["type", "provider", "external_id", "title", "url", "status", "review_state", "is_primary", "summary", "metadata_json"]);
-      for (const [key, value] of Object.entries(patch)) {
-        const col = key.replace(/[A-Z]/g, (c) => `_${c.toLowerCase()}`);
-        if (ALLOWED.has(col)) {
+      const values: SQLInputValue[] = [ts];
+      const map: Array<[keyof typeof patch, string, (v: unknown) => SQLInputValue]> = [
+        ["type", "type", (v) => (v as string) ?? null],
+        ["provider", "provider", (v) => (v as string) ?? null],
+        ["externalId", "external_id", (v) => (v as string | null) ?? null],
+        ["title", "title", (v) => (v as string) ?? null],
+        ["url", "url", (v) => (v as string | null) ?? null],
+        ["status", "status", (v) => (v as string) ?? null],
+        ["reviewState", "review_state", (v) => (v as string) ?? null],
+        ["isPrimary", "is_primary", (v) => (v ? 1 : 0)],
+        ["summary", "summary", (v) => (v as string | null) ?? null],
+        ["metadataJson", "metadata_json", (v) => (v as string | null) ?? null],
+      ];
+      for (const [key, col, coerce] of map) {
+        if (key in patch) {
           sets.push(`${col} = ?`);
-          values.push(col === "is_primary" ? (value ? 1 : 0) : value ?? null);
+          values.push(coerce(patch[key]));
         }
       }
       values.push(id, companyId);
-      getDb().prepare(`UPDATE work_products SET ${sets.join(", ")} WHERE id = ? AND company_id = ?`).run(...(values as SQLInputValue[]));
+      const result = getDb()
+        .prepare(`UPDATE work_products SET ${sets.join(", ")} WHERE id = ? AND company_id = ?`)
+        .run(...values);
+      return Number(result.changes ?? 0);
     },
 
     listWorkProductsForTask(taskId: string, companyId: string) {
@@ -247,8 +275,11 @@ export function buildDocumentMethods(
       }));
     },
 
-    deleteWorkProduct(id: string, companyId: string): void {
-      getDb().prepare("DELETE FROM work_products WHERE id = ? AND company_id = ?").run(id, companyId);
+    deleteWorkProduct(id: string, companyId: string): number {
+      const result = getDb()
+        .prepare("DELETE FROM work_products WHERE id = ? AND company_id = ?")
+        .run(id, companyId);
+      return Number(result.changes ?? 0);
     },
 
     // ── Task-Document Links ──

src/main/prompt-builder/system-prompt.ts

@@ -19,27 +19,15 @@ import {
   buildDepartmentSection,
 } from "./operating-instructions";
 import type { PromptContext } from "./index";
-
-const LEADERSHIP_KEYWORDS = [
-  "chief",
-  "cto",
-  "cmo",
-  "coo",
-  "cfo",
-  "vp",
-  "vice president",
-  "head",
-  "director",
-  "manager",
-  "lead",
-];
+import { roleMatchesLeadershipKeywords } from "../agent-role-helpers";
 
 function isLeadershipRole(ctx: PromptContext): boolean {
+  // HR roles inherit leadership scope for manager-style prompts;
+  // other departments rely on role/title keyword tokenization.
   if (ctx.agent.department === "hr") {
     return true;
   }
-  const text = `${ctx.agent.role} ${ctx.agent.title ?? ""}`.toLowerCase();
-  return LEADERSHIP_KEYWORDS.some((keyword) => text.includes(keyword));
+  return roleMatchesLeadershipKeywords(ctx.agent.role, ctx.agent.title ?? null);
 }
 
 function buildSkillManifest(