diff --git a/ui/src/pages/CompanyExport.tsx b/ui/src/pages/CompanyExport.tsx
index 7a33d15d..32e7458e 100644
--- a/ui/src/pages/CompanyExport.tsx
+++ b/ui/src/pages/CompanyExport.tsx
@@ -1,6 +1,6 @@
 import { useEffect, useMemo, useRef, useState } from "react";
 import { useMutation } from "@tanstack/react-query";
-import type { CompanyPortabilityExportResult } from "@paperclipai/shared";
+import type { CompanyPortabilityExportResult, CompanyPortabilityManifest } from "@paperclipai/shared";
 import { useCompany } from "../context/CompanyContext";
 import { useBreadcrumbs } from "../context/BreadcrumbContext";
 import { useToast } from "../context/ToastContext";
@@ -323,15 +323,133 @@ function FrontmatterCard({
   );
 }
 
+// ── Client-side README generation ────────────────────────────────────
+
+const ROLE_LABELS: Record<string, string> = {
+  ceo: "CEO", cto: "CTO", cmo: "CMO", cfo: "CFO", coo: "COO",
+  vp: "VP", manager: "Manager", engineer: "Engineer", agent: "Agent",
+};
+
+/**
+ * Regenerate README.md content based on the currently checked files.
+ * Only counts/lists entities whose files are in the checked set.
+ */
+function generateReadmeFromSelection(
+  manifest: CompanyPortabilityManifest,
+  checkedFiles: Set<string>,
+  companyName: string,
+  companyDescription: string | null,
+): string {
+  const slugs = checkedSlugs(checkedFiles);
+  const hasOrgChart = checkedFiles.has("images/org-chart.svg");
+
+  const agents = manifest.agents.filter((a) => slugs.agents.has(a.slug));
+  const projects = manifest.projects.filter((p) => slugs.projects.has(p.slug));
+  const tasks = manifest.issues.filter((t) => slugs.tasks.has(t.slug));
+  const skills = manifest.skills.filter((s) => {
+    // Skill files live under skills/{key}/...
+    return [...checkedFiles].some((f) => f.startsWith(`skills/${s.key}/`) || f.startsWith(`skills/`) && f.includes(`/${s.slug}/`));
+  });
+
+  const lines: string[] = [];
+  lines.push(`# ${companyName}`);
+  lines.push("");
+  if (companyDescription) {
+    lines.push(`> ${companyDescription}`);
+    lines.push("");
+  }
+  if (hasOrgChart) {
+    lines.push(`![Org Chart](images/org-chart.svg)`);
+    lines.push("");
+  }
+
+  lines.push("## What's Inside");
+  lines.push("");
+  lines.push("This is an [Agent Company](https://paperclip.ing) package.");
+  lines.push("");
+
+  const counts: Array<[string, number]> = [];
+  if (agents.length > 0) counts.push(["Agents", agents.length]);
+  if (projects.length > 0) counts.push(["Projects", projects.length]);
+  if (skills.length > 0) counts.push(["Skills", skills.length]);
+  if (tasks.length > 0) counts.push(["Tasks", tasks.length]);
+
+  if (counts.length > 0) {
+    lines.push("| Content | Count |");
+    lines.push("|---------|-------|");
+    for (const [label, count] of counts) {
+      lines.push(`| ${label} | ${count} |`);
+    }
+    lines.push("");
+  }
+
+  if (agents.length > 0) {
+    lines.push("### Agents");
+    lines.push("");
+    lines.push("| Agent | Role | Reports To |");
+    lines.push("|-------|------|------------|");
+    for (const agent of agents) {
+      const roleLabel = ROLE_LABELS[agent.role] ?? agent.role;
+      const reportsTo = agent.reportsToSlug ?? "\u2014";
+      lines.push(`| ${agent.name} | ${roleLabel} | ${reportsTo} |`);
+    }
+    lines.push("");
+  }
+
+  if (projects.length > 0) {
+    lines.push("### Projects");
+    lines.push("");
+    for (const project of projects) {
+      const desc = project.description ? ` \u2014 ${project.description}` : "";
+      lines.push(`- **${project.name}**${desc}`);
+    }
+    lines.push("");
+  }
+
+  lines.push("## Getting Started");
+  lines.push("");
+  lines.push("```bash");
+  lines.push("pnpm paperclipai company import this-github-url-or-folder");
+  lines.push("```");
+  lines.push("");
+  lines.push("See [Paperclip](https://paperclip.ing) for more information.");
+  lines.push("");
+  lines.push("---");
+  lines.push(`Exported from [Paperclip](https://paperclip.ing) on ${new Date().toISOString().split("T")[0]}`);
+  lines.push("");
+
+  return lines.join("\n");
+}
+
+/**
+ * Resolve relative image paths in markdown content using the export files map.
+ * Converts SVG references to inline data URIs so they render in the preview.
+ */
+function resolveMarkdownImages(markdown: string, files: Record<string, string>): string {
+  return markdown.replace(
+    /!\[([^\]]*)\]\(([^)]+)\)/g,
+    (_match, alt: string, src: string) => {
+      const svgContent = files[src];
+      if (svgContent && src.endsWith(".svg")) {
+        const dataUri = `data:image/svg+xml;base64,${btoa(svgContent)}`;
+        return `![${alt}](${dataUri})`;
+      }
+      return _match;
+    },
+  );
+}
+
 // ── Preview pane ──────────────────────────────────────────────────────
 
 function ExportPreviewPane({
   selectedFile,
   content,
+  files,
   onSkillClick,
 }: {
   selectedFile: string | null;
   content: string | null;
+  files: Record<string, string>;
   onSkillClick?: (skill: string) => void;
 }) {
   if (!selectedFile || content === null) {
@@ -343,6 +461,9 @@ function ExportPreviewPane({
   const isMarkdown = selectedFile.endsWith(".md");
   const isSvg = selectedFile.endsWith(".svg");
   const parsed = isMarkdown ? parseFrontmatter(content) : null;
+  // Resolve relative image paths (e.g. images/org-chart.svg) for markdown preview
+  const resolvedBody = parsed?.body ? resolveMarkdownImages(parsed.body, files) : null;
+  const resolvedContent = isMarkdown && !parsed ? resolveMarkdownImages(content, files) : content;
 
   return (
     <div className="min-w-0">
@@ -353,10 +474,10 @@ function ExportPreviewPane({
         {parsed ? (
           <>
             <FrontmatterCard data={parsed.data} onSkillClick={onSkillClick} />
-            {parsed.body.trim() && <MarkdownBody>{parsed.body}</MarkdownBody>}
+            {resolvedBody?.trim() && <MarkdownBody>{resolvedBody}</MarkdownBody>}
           </>
         ) : isMarkdown ? (
-          <MarkdownBody>{content}</MarkdownBody>
+          <MarkdownBody>{resolvedContent}</MarkdownBody>
         ) : isSvg ? (
           <div
             className="flex justify-center overflow-auto rounded-lg border border-border bg-white p-4"
@@ -453,16 +574,32 @@ export function CompanyExport() {
     };
   }, [tree, treeSearch, checkedFiles, taskLimit]);
 
-  // Recompute .paperclip.yaml content whenever checked files change so
-  // the preview & download always reflect the current selection.
+  // Recompute .paperclip.yaml and README.md content whenever checked files
+  // change so the preview & download always reflect the current selection.
   const effectiveFiles = useMemo(() => {
     if (!exportData) return {} as Record<string, string>;
-    const yamlPath = exportData.paperclipExtensionPath;
-    if (!yamlPath || !exportData.files[yamlPath]) return exportData.files;
     const filtered = { ...exportData.files };
-    filtered[yamlPath] = filterPaperclipYaml(exportData.files[yamlPath], checkedFiles);
+
+    // Filter .paperclip.yaml
+    const yamlPath = exportData.paperclipExtensionPath;
+    if (yamlPath && exportData.files[yamlPath]) {
+      filtered[yamlPath] = filterPaperclipYaml(exportData.files[yamlPath], checkedFiles);
+    }
+
+    // Regenerate README.md based on checked selection
+    if (exportData.files["README.md"]) {
+      const companyName = exportData.manifest.company?.name ?? selectedCompany?.name ?? "Company";
+      const companyDescription = exportData.manifest.company?.description ?? null;
+      filtered["README.md"] = generateReadmeFromSelection(
+        exportData.manifest,
+        checkedFiles,
+        companyName,
+        companyDescription,
+      );
+    }
+
     return filtered;
-  }, [exportData, checkedFiles]);
+  }, [exportData, checkedFiles, selectedCompany?.name]);
 
   const totalFiles = useMemo(() => countFiles(tree), [tree]);
   const selectedCount = checkedFiles.size;
@@ -671,7 +808,7 @@ export function CompanyExport() {
           </div>
         </aside>
         <div className="min-w-0 overflow-y-auto pl-6">
-          <ExportPreviewPane selectedFile={selectedFile} content={previewContent} onSkillClick={handleSkillClick} />
+          <ExportPreviewPane selectedFile={selectedFile} content={previewContent} files={effectiveFiles} onSkillClick={handleSkillClick} />
         </div>
       </div>
     </div>