diff --git a/ui/src/components/OnboardingChat.tsx b/ui/src/components/OnboardingChat.tsx
new file mode 100644
index 00000000..045d579d
--- /dev/null
+++ b/ui/src/components/OnboardingChat.tsx
@@ -0,0 +1,211 @@
+import { useState, useRef, useEffect, useCallback } from "react";
+import { useQuery, useQueryClient } from "@tanstack/react-query";
+import type { IssueComment } from "@paperclipai/shared";
+import { issuesApi } from "../api/issues";
+import { queryKeys } from "../lib/queryKeys";
+import { Button } from "@/components/ui/button";
+import { MarkdownBody } from "./MarkdownBody";
+import { cn } from "../lib/utils";
+import { Loader2, Send, CheckCircle2 } from "lucide-react";
+
+interface OnboardingChatProps {
+  taskId: string;
+  agentName: string;
+  onPlanDetected?: (planMarkdown: string) => void;
+}
+
+/**
+ * Detects whether a comment body contains a structured hiring plan.
+ * Looks for markdown headers or bullet lists that mention roles/positions.
+ */
+function detectHiringPlan(body: string): boolean {
+  const planPatterns = [
+    /##?\s*(hiring|team|org|roles|plan)/i,
+    /##?\s*(proposed|recommended)\s*(roles|hires|team)/i,
+    /\n-\s+\*\*[^*]+\*\*/g, // bullet list with bold items (role names)
+    /\|\s*role\s*\|/i, // markdown table with "Role" header
+  ];
+  return planPatterns.some((pattern) => pattern.test(body));
+}
+
+export function OnboardingChat({
+  taskId,
+  agentName,
+  onPlanDetected,
+}: OnboardingChatProps) {
+  const queryClient = useQueryClient();
+  const [input, setInput] = useState("");
+  const [sending, setSending] = useState(false);
+  const [detectedPlanCommentId, setDetectedPlanCommentId] = useState<
+    string | null
+  >(null);
+  const scrollRef = useRef<HTMLDivElement>(null);
+  const inputRef = useRef<HTMLTextAreaElement>(null);
+
+  const {
+    data: comments,
+    isLoading,
+  } = useQuery({
+    queryKey: queryKeys.issues.comments(taskId),
+    queryFn: () => issuesApi.listComments(taskId),
+    refetchInterval: 4000,
+  });
+
+  // Auto-scroll to bottom when new comments arrive
+  useEffect(() => {
+    if (scrollRef.current) {
+      scrollRef.current.scrollTop = scrollRef.current.scrollHeight;
+    }
+  }, [comments?.length]);
+
+  // Detect hiring plan in agent comments
+  useEffect(() => {
+    if (!comments || !onPlanDetected || detectedPlanCommentId) return;
+    // Scan from newest to oldest for a plan-like comment from the agent
+    for (let i = comments.length - 1; i >= 0; i--) {
+      const c = comments[i];
+      if (c.authorAgentId && detectHiringPlan(c.body)) {
+        setDetectedPlanCommentId(c.id);
+        onPlanDetected(c.body);
+        break;
+      }
+    }
+  }, [comments, onPlanDetected, detectedPlanCommentId]);
+
+  const handleSend = useCallback(async () => {
+    const body = input.trim();
+    if (!body || sending) return;
+    setSending(true);
+    try {
+      await issuesApi.addComment(taskId, body);
+      setInput("");
+      queryClient.invalidateQueries({
+        queryKey: queryKeys.issues.comments(taskId),
+      });
+    } finally {
+      setSending(false);
+      inputRef.current?.focus();
+    }
+  }, [input, sending, taskId, queryClient]);
+
+  const handleKeyDown = useCallback(
+    (e: React.KeyboardEvent) => {
+      if (e.key === "Enter" && !e.shiftKey) {
+        e.preventDefault();
+        handleSend();
+      }
+    },
+    [handleSend],
+  );
+
+  const lastComment = comments?.[comments.length - 1];
+  const isWaitingForAgent =
+    lastComment && lastComment.authorUserId && !lastComment.authorAgentId;
+
+  if (isLoading) {
+    return (
+      <div className="flex items-center justify-center py-8 text-muted-foreground text-sm">
+        <Loader2 className="h-4 w-4 mr-2 animate-spin" />
+        Loading conversation...
+      </div>
+    );
+  }
+
+  return (
+    <div className="flex flex-col h-full">
+      {/* Messages */}
+      <div
+        ref={scrollRef}
+        className="flex-1 overflow-y-auto space-y-3 mb-3 min-h-[180px] max-h-[320px] pr-1"
+      >
+        {(!comments || comments.length === 0) && (
+          <p className="text-sm text-muted-foreground text-center py-4">
+            Starting conversation with {agentName}...
+          </p>
+        )}
+        {comments?.map((comment) => {
+          const isAgent = Boolean(comment.authorAgentId);
+          const isPlan =
+            detectedPlanCommentId === comment.id;
+          return (
+            <div
+              key={comment.id}
+              className={cn(
+                "rounded-md px-3 py-2 text-sm",
+                isAgent
+                  ? "bg-muted/50 border border-border mr-8"
+                  : "bg-accent/50 border border-accent ml-8",
+              )}
+            >
+              <div className="flex items-center gap-1.5 mb-1">
+                <span
+                  className={cn(
+                    "text-[10px] font-medium uppercase tracking-wide",
+                    isAgent
+                      ? "text-muted-foreground"
+                      : "text-foreground/70",
+                  )}
+                >
+                  {isAgent ? agentName : "You"}
+                </span>
+                {isPlan && (
+                  <span className="inline-flex items-center gap-0.5 text-[10px] text-green-600 dark:text-green-400 font-medium">
+                    <CheckCircle2 className="h-3 w-3" />
+                    Hiring plan detected
+                  </span>
+                )}
+              </div>
+              <div className="prose prose-sm dark:prose-invert max-w-none [&>*:first-child]:mt-0 [&>*:last-child]:mb-0">
+                <MarkdownBody>{comment.body}</MarkdownBody>
+              </div>
+            </div>
+          );
+        })}
+
+        {/* Thinking indicator */}
+        {isWaitingForAgent && (
+          <div className="flex items-center gap-2 text-sm text-muted-foreground px-3 py-2">
+            <Loader2 className="h-3.5 w-3.5 animate-spin" />
+            {agentName} is thinking...
+          </div>
+        )}
+      </div>
+
+      {/* Input area */}
+      <div className="flex items-end gap-2 border-t border-border pt-3">
+        <textarea
+          ref={inputRef}
+          className="flex-1 rounded-md border border-border bg-transparent px-3 py-2 text-sm outline-none focus:ring-1 focus:ring-ring placeholder:text-muted-foreground/50 resize-none min-h-[40px] max-h-[100px]"
+          placeholder="Message your CEO..."
+          value={input}
+          onChange={(e) => setInput(e.target.value)}
+          onKeyDown={handleKeyDown}
+          rows={1}
+          autoFocus
+        />
+        <Button
+          size="sm"
+          disabled={!input.trim() || sending}
+          onClick={handleSend}
+          className="shrink-0"
+        >
+          {sending ? (
+            <Loader2 className="h-3.5 w-3.5 animate-spin" />
+          ) : (
+            <Send className="h-3.5 w-3.5" />
+          )}
+        </Button>
+      </div>
+
+      {/* Manual plan selection */}
+      {!detectedPlanCommentId &&
+        comments &&
+        comments.some((c) => c.authorAgentId) && (
+          <p className="text-[10px] text-muted-foreground mt-2">
+            If the CEO has proposed a plan, click "Next" once you're satisfied,
+            or keep chatting to refine it.
+          </p>
+        )}
+    </div>
+  );
+}
diff --git a/ui/src/components/OnboardingWizard.tsx b/ui/src/components/OnboardingWizard.tsx
index 8d746be7..62b5bfe2 100644
--- a/ui/src/components/OnboardingWizard.tsx
+++ b/ui/src/components/OnboardingWizard.tsx
@@ -30,6 +30,7 @@ import {
 } from "@paperclipai/adapter-codex-local";
 import { DEFAULT_CURSOR_LOCAL_MODEL } from "@paperclipai/adapter-cursor-local";
 import { DEFAULT_GEMINI_LOCAL_MODEL } from "@paperclipai/adapter-gemini-local";
+import { OnboardingChat } from "./OnboardingChat";
 import { AsciiArtAnimation } from "./AsciiArtAnimation";
 import { ChoosePathButton } from "./PathInstructionsModal";
 import { HintIcon } from "./agent-config-primitives";
@@ -146,6 +147,10 @@ export function OnboardingWizard() {
     el.style.height = el.scrollHeight + "px";
   }, []);
 
+  // Planning task + hiring plan
+  const [planningTaskId, setPlanningTaskId] = useState<string | null>(null);
+  const [planContent, setPlanContent] = useState<string | null>(null);
+
   // Created entity IDs — pre-populate from existing company when skipping step 1
   const [createdCompanyId, setCreatedCompanyId] = useState<string | null>(
     existingCompanyId ?? null
@@ -277,6 +282,8 @@ export function OnboardingWizard() {
     setQ2("");
     setQ3("");
     setQ4("");
+    setPlanningTaskId(null);
+    setPlanContent(null);
     setAgentName("CEO");
     setAdapterType("claude_local");
     setCwd("");
@@ -462,6 +469,20 @@ export function OnboardingWizard() {
       queryClient.invalidateQueries({
         queryKey: queryKeys.agents.list(createdCompanyId)
       });
+
+      // Create the planning task and kick off the conversation
+      const planningIssue = await issuesApi.create(createdCompanyId, {
+        title: "Build hiring plan with CEO",
+        description: `Company mission: ${companyGoal}\n\nCollaborate with the board to create a hiring plan for the company.`,
+        assigneeAgentId: agent.id,
+        status: "in_progress"
+      });
+      setPlanningTaskId(planningIssue.id);
+      await issuesApi.addComment(
+        planningIssue.id,
+        `Our company mission is: ${companyGoal}\n\nLet's build a hiring plan together. What roles do you think we need to accomplish this mission?`
+      );
+
       setStep(4);
     } catch (err) {
       setError(err instanceof Error ? err.message : "Failed to create agent");
@@ -1342,9 +1363,9 @@ export function OnboardingWizard() {
                 </div>
               )}
 
-              {/* Step 4: Chat with CEO — placeholder for OnboardingChat component */}
+              {/* Step 4: Chat with CEO */}
               {step === 4 && (
-                <div className="space-y-5">
+                <div className="space-y-4">
                   <div className="flex items-center gap-3 mb-1">
                     <div className="bg-muted/50 p-2">
                       <Sparkles className="h-5 w-5 text-muted-foreground" />
@@ -1357,11 +1378,19 @@ export function OnboardingWizard() {
                       </p>
                     </div>
                   </div>
-                  <div className="rounded-md border border-border p-4 min-h-[200px] flex items-center justify-center">
-                    <p className="text-sm text-muted-foreground">
-                      Chat component coming soon — skip to review a sample hiring plan.
-                    </p>
-                  </div>
+                  {planningTaskId ? (
+                    <OnboardingChat
+                      taskId={planningTaskId}
+                      agentName={agentName}
+                      onPlanDetected={(md) => setPlanContent(md)}
+                    />
+                  ) : (
+                    <div className="rounded-md border border-border p-4 min-h-[200px] flex items-center justify-center">
+                      <p className="text-sm text-muted-foreground">
+                        No planning task found. Go back and create your CEO first.
+                      </p>
+                    </div>
+                  )}
                 </div>
               )}