diff --git a/site/package-lock.json b/site/package-lock.json
index 657c18c..019e8fb 100644
--- a/site/package-lock.json
+++ b/site/package-lock.json
@@ -8,6 +8,7 @@
             "name": "dynavera",
             "version": "0.0.0",
             "dependencies": {
+                "@vueuse/core": "^14.2.1",
                 "ant-design-vue": "^4.2.6",
                 "axios": "^1.13.2",
                 "dompurify": "^3.3.1",
@@ -100,6 +101,7 @@
             "integrity": "sha512-H3mcG6ZDLTlYfaSNi0iOKkigqMFvkTKlGUYlD8GW7nNOYRrevuA46iTypPyv+06V3fEmvvazfntkBU34L0azAw==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "@babel/code-frame": "^7.28.6",
                 "@babel/generator": "^7.28.6",
@@ -1745,6 +1747,7 @@
             "integrity": "sha512-ne4A0IpG3+2ETuREInjPNhUGis1SFjv1d5asp8MzEAGtOZeTeHVDOYqOgqfhvseqg/iXty2hjBf1zAOb7RNiNw==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "undici-types": "~7.16.0"
             }
@@ -1756,6 +1759,12 @@
             "devOptional": true,
             "license": "MIT"
         },
+        "node_modules/@types/web-bluetooth": {
+            "version": "0.0.21",
+            "resolved": "https://registry.npmjs.org/@types/web-bluetooth/-/web-bluetooth-0.0.21.tgz",
+            "integrity": "sha512-oIQLCGWtcFZy2JW77j9k8nHzAOpqMHLQejDA48XXMWH6tjCQHz5RCFz1bzsmROyL6PUm+LLnUiI4BCn221inxA==",
+            "license": "MIT"
+        },
         "node_modules/@typescript-eslint/eslint-plugin": {
             "version": "8.53.0",
             "resolved": "https://registry.npmjs.org/@typescript-eslint/eslint-plugin/-/eslint-plugin-8.53.0.tgz",
@@ -1801,6 +1810,7 @@
             "integrity": "sha512-npiaib8XzbjtzS2N4HlqPvlpxpmZ14FjSJrteZpPxGUaYPlvhzlzUZ4mZyABo0EFrOWnvyd0Xxroq//hKhtAWg==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "@typescript-eslint/scope-manager": "8.53.0",
                 "@typescript-eslint/types": "8.53.0",
@@ -2431,12 +2441,51 @@
                 }
             }
         },
+        "node_modules/@vueuse/core": {
+            "version": "14.2.1",
+            "resolved": "https://registry.npmjs.org/@vueuse/core/-/core-14.2.1.tgz",
+            "integrity": "sha512-3vwDzV+GDUNpdegRY6kzpLm4Igptq+GA0QkJ3W61Iv27YWwW/ufSlOfgQIpN6FZRMG0mkaz4gglJRtq5SeJyIQ==",
+            "license": "MIT",
+            "dependencies": {
+                "@types/web-bluetooth": "^0.0.21",
+                "@vueuse/metadata": "14.2.1",
+                "@vueuse/shared": "14.2.1"
+            },
+            "funding": {
+                "url": "https://github.com/sponsors/antfu"
+            },
+            "peerDependencies": {
+                "vue": "^3.5.0"
+            }
+        },
+        "node_modules/@vueuse/metadata": {
+            "version": "14.2.1",
+            "resolved": "https://registry.npmjs.org/@vueuse/metadata/-/metadata-14.2.1.tgz",
+            "integrity": "sha512-1ButlVtj5Sb/HDtIy1HFr1VqCP4G6Ypqt5MAo0lCgjokrk2mvQKsK2uuy0vqu/Ks+sHfuHo0B9Y9jn9xKdjZsw==",
+            "license": "MIT",
+            "funding": {
+                "url": "https://github.com/sponsors/antfu"
+            }
+        },
+        "node_modules/@vueuse/shared": {
+            "version": "14.2.1",
+            "resolved": "https://registry.npmjs.org/@vueuse/shared/-/shared-14.2.1.tgz",
+            "integrity": "sha512-shTJncjV9JTI4oVNyF1FQonetYAiTBd+Qj7cY89SWbXSkx7gyhrgtEdF2ZAVWS1S3SHlaROO6F2IesJxQEkZBw==",
+            "license": "MIT",
+            "funding": {
+                "url": "https://github.com/sponsors/antfu"
+            },
+            "peerDependencies": {
+                "vue": "^3.5.0"
+            }
+        },
         "node_modules/acorn": {
             "version": "8.15.0",
             "resolved": "https://registry.npmjs.org/acorn/-/acorn-8.15.0.tgz",
             "integrity": "sha512-NZyJarBfL7nWwIq+FDL6Zp/yHEhePMNnnJ0y3qfieCrmNvYct8uvtiV41UvlSe6apAfk0fY1FbWx+NwfmpvtTg==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "bin": {
                 "acorn": "bin/acorn"
             },
@@ -2666,6 +2715,7 @@
                 }
             ],
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "baseline-browser-mapping": "^2.9.0",
                 "caniuse-lite": "^1.0.30001759",
@@ -3215,6 +3265,7 @@
             "integrity": "sha512-LEyamqS7W5HB3ujJyvi0HQK/dtVINZvd5mAAp9eT5S/ujByGjiZLCzPcHVzuXbpJDJF/cxwHlfceVUDZ2lnSTw==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "@eslint-community/eslint-utils": "^4.8.0",
                 "@eslint-community/regexpp": "^4.12.1",
@@ -3275,6 +3326,7 @@
             "integrity": "sha512-82GZUjRS0p/jganf6q1rEO25VSoHH0hKPCTrgillPjdI/3bgBhAE1QzHrHTizjpRvy6pGAvKjDJtk2pF9NDq8w==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "bin": {
                 "eslint-config-prettier": "bin/cli.js"
             },
@@ -3322,6 +3374,7 @@
             "integrity": "sha512-nA5yUs/B1KmKzvC42fyD0+l9Yd+LtEpVhWRbXuDj0e+ZURcTtyRbMDWUeJmTAh2wC6jC83raS63anNM2YT3NPw==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "@eslint-community/eslint-utils": "^4.4.0",
                 "natural-compare": "^1.4.0",
@@ -4018,6 +4071,7 @@
             "integrity": "sha512-ekilCSN1jwRvIbgeg/57YFh8qQDNbwDb9xT/qu2DAHbFFZUicIl4ygVaAvzveMhMVr3LnpSKTNnwt8PoOfmKhQ==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "bin": {
                 "jiti": "lib/jiti-cli.mjs"
             }
@@ -4696,6 +4750,7 @@
             "integrity": "sha512-v6UNi1+3hSlVvv8fSaoUbggEM5VErKmmpGA7Pl3HF8V6uKY7rvClBOJlH6yNwQtfTueNkGVpOv/mtWL9L4bgRA==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "bin": {
                 "prettier": "bin/prettier.cjs"
             },
@@ -5143,6 +5198,7 @@
             "integrity": "sha512-5gTmgEY/sqK6gFXLIsQNH19lWb4ebPDLA4SdLP7dsWkIXHWlG66oPuVvXSGFPppYZz8ZDZq0dYYrbHfBCVUb1Q==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "engines": {
                 "node": ">=12"
             },
@@ -5222,6 +5278,7 @@
             "integrity": "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw==",
             "devOptional": true,
             "license": "Apache-2.0",
+            "peer": true,
             "bin": {
                 "tsc": "bin/tsc",
                 "tsserver": "bin/tsserver"
@@ -5345,6 +5402,7 @@
             "integrity": "sha512-w+N7Hifpc3gRjZ63vYBXA56dvvRlNWRczTdmCBBa+CotUzAPf5b7YMdMR/8CQoeYE5LX3W4wj6RYTgonm1b9DA==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "esbuild": "^0.27.0",
                 "fdir": "^6.5.0",
@@ -5635,6 +5693,7 @@
             "integrity": "sha512-5gTmgEY/sqK6gFXLIsQNH19lWb4ebPDLA4SdLP7dsWkIXHWlG66oPuVvXSGFPppYZz8ZDZq0dYYrbHfBCVUb1Q==",
             "dev": true,
             "license": "MIT",
+            "peer": true,
             "engines": {
                 "node": ">=12"
             },
@@ -5654,6 +5713,7 @@
             "resolved": "https://registry.npmjs.org/vue/-/vue-3.5.26.tgz",
             "integrity": "sha512-SJ/NTccVyAoNUJmkM9KUqPcYlY+u8OVL1X5EW9RIs3ch5H2uERxyyIUI4MRxVCSOiEcupX9xNGde1tL9ZKpimA==",
             "license": "MIT",
+            "peer": true,
             "dependencies": {
                 "@vue/compiler-dom": "3.5.26",
                 "@vue/compiler-sfc": "3.5.26",
diff --git a/site/package.json b/site/package.json
index 7e997aa..e5f5f78 100644
--- a/site/package.json
+++ b/site/package.json
@@ -18,6 +18,7 @@
         "format": "prettier --write --experimental-cli src/"
     },
     "dependencies": {
+        "@vueuse/core": "^14.2.1",
         "ant-design-vue": "^4.2.6",
         "axios": "^1.13.2",
         "dompurify": "^3.3.1",
diff --git a/site/src/views/OrganizationManage.vue b/site/src/views/OrganizationManage.vue
index 31670f6..e400763 100644
--- a/site/src/views/OrganizationManage.vue
+++ b/site/src/views/OrganizationManage.vue
@@ -1,5 +1,5 @@
 <script setup lang="ts">
-import { ref, onMounted, computed } from 'vue'
+import { ref, onMounted, computed, h } from 'vue'
 import { useRoute, useRouter } from 'vue-router'
 import {
     Card,
@@ -14,6 +14,10 @@ import {
     Modal,
     Tabs,
     InputNumber,
+    Select,
+    Upload,
+    Steps,
+    Table,
 } from 'ant-design-vue'
 import { apiClient, isAxiosError, API } from '../router/api'
 import { useUserStore } from '../stores/userStore'
@@ -21,6 +25,8 @@ import type { Organization } from '../types/organization'
 import type { User } from '../types/user'
 import type { InviteToken } from '../types/organization'
 import type { Role } from '../types/organization'
+import type { TrainingFile } from '../types/organization'
+import { InboxOutlined, DeleteOutlined } from '@ant-design/icons-vue'
 
 const route = useRoute()
 const router = useRouter()
@@ -32,15 +38,27 @@ const members = ref<User[]>([])
 const invites = ref<InviteToken[]>([])
 const newInviteMaxUses = ref<number>(1)
 const Roles = ref<Role[]>([])
+const trainingFiles = ref<TrainingFile[]>([])
 const memberSearch = ref('')
 const roleSearch = ref('')
 const loading = ref(false)
-const creatingRole = ref(false)
 const deletingRoleUuid = ref<string | null>(null)
 const roleModalVisible = ref(false)
 const roleMembersModalVisible = ref(false)
 const selectedRoleForMembers = ref<Role | null>(null)
 const selectedRoleMembers = ref<User[]>([])
+const roleWizardStep = ref(0)
+const creatingRoleWizard = ref(false)
+const createdRoleForWizard = ref<Role | null>(null)
+const wizardSelectedFile = ref<File | null>(null)
+const wizardFileDescription = ref('')
+const wizardUploading = ref(false)
+const wizardUploadedFiles = ref<TrainingFile[]>([])
+const uploadModalVisible = ref(false)
+const uploadRoleUuid = ref('')
+const uploadSelectedFile = ref<File | null>(null)
+const uploadFileDescription = ref('')
+const uploadingFile = ref(false)
 const createRoleForm = ref({
     name: '',
     description: '',
@@ -122,43 +140,333 @@ const fetchRoles = async () => {
     }
 }
 
-const resetRoleForm = () => {
+const fetchTrainingFiles = async () => {
+    try {
+        const response = await apiClient.get<TrainingFile[]>(API.knowledge.trainingFiles.list(), {
+            params: { organization_uuid: organizationUuid },
+        })
+        trainingFiles.value = response.data
+    } catch (error) {
+        console.error('Failed to fetch training files:', error)
+    }
+}
+
+
+const resetRoleWizard = () => {
+    roleWizardStep.value = 0
     createRoleForm.value = { name: '', description: '' }
+    createdRoleForWizard.value = null
+    wizardSelectedFile.value = null
+    wizardFileDescription.value = ''
+    wizardUploadedFiles.value = []
+    creatingRoleWizard.value = false
+    wizardUploading.value = false
+}
+
+const closeRoleWizard = () => {
+    roleModalVisible.value = false
+    resetRoleWizard()
+}
+
+const openRoleWizard = () => {
+    resetRoleWizard()
+    roleModalVisible.value = true
 }
 
 const hasDuplicateRoleName = (name: string) =>
     Roles.value.some((role) => role.name.trim().toLowerCase() === name.trim().toLowerCase())
 
-const createRole = async () => {
+const allowedExtensions = ['txt', 'pdf', 'md', 'csv', 'json', 'docx', 'doc']
+const maxUploadBytes = 50 * 1024 * 1024
+
+const validateUploadFile = (file: File): boolean => {
+    const extension = file.name.split('.').pop()?.toLowerCase()
+
+    if (!extension || !allowedExtensions.includes(extension)) {
+        message.error(
+            `File type ".${extension}" is not allowed. Allowed types: ${allowedExtensions.join(', ')}`,
+        )
+        return false
+    }
+
+    if (file.size > maxUploadBytes) {
+        message.error(
+            `File size must not exceed 50MB. Current size: ${(file.size / 1024 / 1024).toFixed(2)}MB`,
+        )
+        return false
+    }
+
+    return true
+}
+
+const uploadTrainingFile = async (
+    roleUuid: string,
+    file: File,
+    description: string,
+): Promise<TrainingFile | null> => {
+    const formData = new FormData()
+    formData.append('file', file)
+    formData.append('file_name', file.name)
+    formData.append('description', description)
+    formData.append('role_uuid', roleUuid)
+
+    try {
+        const response = await apiClient.post<TrainingFile>(API.knowledge.trainingFiles.list(), formData, {
+            headers: {
+                'Content-Type': 'multipart/form-data',
+            },
+        })
+        return response.data
+    } catch (error) {
+        if (isAxiosError(error)) {
+            const errorMsg =
+                error.response?.data?.error ||
+                error.response?.data?.file?.[0] ||
+                'Failed to upload file'
+            message.error(errorMsg)
+        } else {
+            message.error('Failed to upload file')
+        }
+        return null
+    }
+}
+
+const getTrainingFilesByRole = (roleUuid: string): TrainingFile[] =>
+    trainingFiles.value.filter((file) => file.role?.uuid === roleUuid)
+
+const deleteTrainingFile = async (uuid: string, fileName: string) => {
+    Modal.confirm({
+        title: 'Delete File',
+        content: `Are you sure you want to delete "${fileName}"? This action cannot be undone.`,
+        okText: 'Delete',
+        okType: 'danger',
+        cancelText: 'Cancel',
+        onOk: async () => {
+            try {
+                await apiClient.delete(API.knowledge.trainingFiles.byId(uuid))
+                message.success('File deleted successfully')
+                trainingFiles.value = trainingFiles.value.filter((file) => file.uuid !== uuid)
+            } catch (error) {
+                console.error('Failed to delete file:', error)
+                message.error('Failed to delete file')
+            }
+        },
+    })
+}
+
+const canDeleteTrainingFile = (record: TrainingFile): boolean => {
+    if (auth.user?.uuid === record.uploaded_by?.uuid) return true
+    if (organization.value?.owner?.uuid === auth.user?.uuid) return true
+    return members.value.some((member) => member.uuid === auth.user?.uuid && member.is_manager)
+}
+
+const formatFileSize = (bytes: number) => {
+    if (bytes === 0) return '0 Bytes'
+    const k = 1024
+    const sizes = ['Bytes', 'KB', 'MB', 'GB']
+    const i = Math.floor(Math.log(bytes) / Math.log(k))
+    return Math.round((bytes / Math.pow(k, i)) * 100) / 100 + ' ' + sizes[i]
+}
+
+const trainingFileColumns = [
+    {
+        title: 'File Name',
+        dataIndex: 'file_name',
+        key: 'file_name',
+    },
+    {
+        title: 'Uploaded By',
+        key: 'uploaded_by',
+        customRender: ({ record }: { record: TrainingFile }) => {
+            if (!record.uploaded_by) return '-'
+            return `${record.uploaded_by.first_name} ${record.uploaded_by.last_name}`
+        },
+    },
+    {
+        title: 'Size',
+        dataIndex: 'file_size',
+        key: 'file_size',
+        customRender: ({ value }: { value: number }) => formatFileSize(value || 0),
+    },
+    {
+        title: 'Role',
+        key: 'role',
+        customRender: ({ record }: { record: TrainingFile }) => record.role?.name || '-',
+    },
+    {
+        title: 'Status',
+        dataIndex: 'status',
+        key: 'status',
+        customRender: ({ value }: { value: string }) => {
+            const statusMap: Record<string, { color: string; label: string }> = {
+                ingesting: { color: 'processing', label: 'Ingesting' },
+                chunked: { color: 'blue', label: 'Chunked' },
+                embedded: { color: 'success', label: 'Embedded' },
+                failed: { color: 'error', label: 'Failed' },
+            }
+            const status = statusMap[value] || { color: 'default', label: value }
+            return h(Tag, { color: status.color }, () => status.label)
+        },
+    },
+    {
+        title: 'Uploaded',
+        dataIndex: 'created_at',
+        key: 'created_at',
+        customRender: ({ value }: { value: string }) => new Date(value).toLocaleDateString(),
+    },
+    {
+        title: 'Action',
+        key: 'action',
+        customRender: ({ record }: { record: TrainingFile }) => {
+            if (canDeleteTrainingFile(record)) {
+                return h(
+                    Button,
+                    {
+                        danger: true,
+                        size: 'small',
+                        icon: h(DeleteOutlined),
+                        onClick: () => deleteTrainingFile(record.uuid, record.file_name),
+                    },
+                    () => 'Delete',
+                )
+            }
+            return null
+        },
+    },
+]
+
+
+const createRoleForWizard = async (): Promise<Role | null> => {
     const name = createRoleForm.value.name.trim()
     const description = createRoleForm.value.description.trim()
 
     if (!name) {
         message.error('Role name is required')
-        return
+        return null
     }
 
     if (hasDuplicateRoleName(name)) {
         message.error('A role with this name already exists')
-        return
+        return null
     }
 
-    creatingRole.value = true
+    creatingRoleWizard.value = true
     try {
-        await apiClient.post(API.roles.list(organizationUuid), { name, description })
-        message.success('Role created successfully')
-        roleModalVisible.value = false
-        resetRoleForm()
+        const response = await apiClient.post<Role>(API.roles.list(organizationUuid), { name, description })
+        message.success('Role created successfully. You can upload training files now.')
         await fetchRoles()
+
+        if (response.data?.uuid) {
+            return response.data
+        }
+
+        return Roles.value.find((role) => role.name.trim().toLowerCase() === name.toLowerCase()) || null
     } catch (error) {
-        console.error('Failed to create role:', error)
+        console.error('Failed to create role in wizard:', error)
         if (isAxiosError(error)) {
             message.error(error.response?.data?.error || 'Failed to create role')
         } else {
             message.error('Failed to create role')
         }
+        return null
     } finally {
-        creatingRole.value = false
+        creatingRoleWizard.value = false
+    }
+}
+
+const handleRoleWizardOk = async () => {
+    if (roleWizardStep.value === 0) {
+        const role = await createRoleForWizard()
+        if (!role) return
+        createdRoleForWizard.value = role
+        roleWizardStep.value = 1
+        return
+    }
+
+    closeRoleWizard()
+}
+
+const handleRoleWizardFileSelected = (file: File) => {
+    if (!validateUploadFile(file)) {
+        wizardSelectedFile.value = null
+        return
+    }
+    wizardSelectedFile.value = file
+}
+
+const uploadFileFromWizard = async () => {
+    const roleUuid = createdRoleForWizard.value?.uuid
+    if (!roleUuid) {
+        message.error('Role is not available for upload')
+        return
+    }
+
+    if (!wizardSelectedFile.value) {
+        message.error('Please select a file to upload')
+        return
+    }
+
+    wizardUploading.value = true
+    try {
+        const uploaded = await uploadTrainingFile(
+            roleUuid,
+            wizardSelectedFile.value,
+            wizardFileDescription.value,
+        )
+        if (!uploaded) return
+
+        trainingFiles.value.unshift(uploaded)
+        wizardUploadedFiles.value.unshift(uploaded)
+        message.success(`File "${wizardSelectedFile.value.name}" uploaded successfully`)
+        wizardSelectedFile.value = null
+        wizardFileDescription.value = ''
+    } finally {
+        wizardUploading.value = false
+    }
+}
+
+const openUploadModal = (role?: Role) => {
+    uploadRoleUuid.value = role?.uuid || ''
+    uploadSelectedFile.value = null
+    uploadFileDescription.value = ''
+    uploadModalVisible.value = true
+}
+
+const handleUploadModalFileSelected = (file: File) => {
+    if (!validateUploadFile(file)) {
+        uploadSelectedFile.value = null
+        return
+    }
+    uploadSelectedFile.value = file
+}
+
+const handleUploadModalOk = async () => {
+    if (!uploadRoleUuid.value) {
+        message.error('Please select a role for this training file')
+        return
+    }
+
+    if (!uploadSelectedFile.value) {
+        message.error('Please select a file to upload')
+        return
+    }
+
+    uploadingFile.value = true
+    try {
+        const uploaded = await uploadTrainingFile(
+            uploadRoleUuid.value,
+            uploadSelectedFile.value,
+            uploadFileDescription.value,
+        )
+        if (!uploaded) return
+
+        trainingFiles.value.unshift(uploaded)
+        message.success(`File "${uploadSelectedFile.value.name}" uploaded successfully`)
+        uploadModalVisible.value = false
+        uploadSelectedFile.value = null
+        uploadFileDescription.value = ''
+    } finally {
+        uploadingFile.value = false
     }
 }
 
@@ -302,6 +610,7 @@ onMounted(async () => {
     await fetchMembers()
     await fetchInvites()
     await fetchRoles()
+    await fetchTrainingFiles()
 
     const currentUserUuid = auth.user?.uuid
     const isOwner = organization.value?.owner?.uuid === currentUserUuid
@@ -472,7 +781,10 @@ onMounted(async () => {
                                         placeholder="Search roles by name or description"
                                         style="width: 300px"
                                     />
-                                    <Button type="primary" @click="roleModalVisible = true">
+                                    <Button @click="openUploadModal()">
+                                        Upload Training File
+                                    </Button>
+                                    <Button type="primary" @click="openRoleWizard">
                                         Create Role
                                     </Button>
                                 </Space>
@@ -485,24 +797,54 @@ onMounted(async () => {
                             >
                                 <template #renderItem="{ item }">
                                     <List.Item class="Role-item">
-                                        <List.Item.Meta
-                                            :title="item.name"
-                                            :description="item.description || 'No description'"
-                                        />
-                                        <Space>
-                                            <Tag>{{ item.member_count }} members</Tag>
-                                            <Button size="small" @click="openRoleMembersModal(item)">
-                                                View Members
-                                            </Button>
-                                            <Button
-                                                danger
-                                                size="small"
-                                                :loading="deletingRoleUuid === item.uuid"
-                                                @click="deleteRole(item)"
-                                            >
-                                                Delete
-                                            </Button>
-                                        </Space>
+                                        <div class="role-content">
+                                            <div class="role-head">
+                                                <List.Item.Meta
+                                                    :title="item.name"
+                                                    :description="item.description || 'No description'"
+                                                />
+                                                <Space>
+                                                    <Tag>{{ item.member_count }} members</Tag>
+                                                    <Tag color="blue">{{ getTrainingFilesByRole(item.uuid).length }} files</Tag>
+                                                    <Button size="small" @click="openUploadModal(item)">
+                                                        Upload Files
+                                                    </Button>
+                                                    <Button size="small" @click="openRoleMembersModal(item)">
+                                                        View Members
+                                                    </Button>
+                                                    <Button
+                                                        danger
+                                                        size="small"
+                                                        :loading="deletingRoleUuid === item.uuid"
+                                                        @click="deleteRole(item)"
+                                                    >
+                                                        Delete
+                                                    </Button>
+                                                </Space>
+                                            </div>
+
+                                            <div class="role-files">
+                                                <Typography.Text strong>Training files for this role</Typography.Text>
+                                                <List
+                                                    v-if="getTrainingFilesByRole(item.uuid).length > 0"
+                                                    :data-source="getTrainingFilesByRole(item.uuid)"
+                                                    size="small"
+                                                    :bordered="false"
+                                                >
+                                                    <template #renderItem="{ item: file }">
+                                                        <List.Item>
+                                                            <Space style="display: flex; justify-content: space-between; width: 100%">
+                                                                <Typography.Text>{{ file.file_name }}</Typography.Text>
+                                                                <Tag>{{ formatFileSize(file.file_size || 0) }}</Tag>
+                                                            </Space>
+                                                        </List.Item>
+                                                    </template>
+                                                </List>
+                                                <Typography.Paragraph v-else type="secondary" style="margin: 0.5rem 0 0">
+                                                    No training files uploaded for this role yet.
+                                                </Typography.Paragraph>
+                                            </div>
+                                        </div>
                                     </List.Item>
                                 </template>
                             </List>
@@ -511,25 +853,53 @@ onMounted(async () => {
                             </Typography.Paragraph>
                         </div>
                     </Tabs.TabPane>
+
+                    <Tabs.TabPane key="files" tab="Files">
+                        <div class="section">
+                            <div class="section-header">
+                                <Typography.Title :level="4" style="color: #1f2937 !important">
+                                    Training Files ({{ trainingFiles.length }})
+                                </Typography.Title>
+                                <Button @click="openUploadModal()">Upload Training File</Button>
+                            </div>
+
+                            <Table
+                                v-if="trainingFiles.length > 0"
+                                :columns="trainingFileColumns"
+                                :data-source="trainingFiles"
+                                :pagination="{ pageSize: 10 }"
+                                :row-key="(record: TrainingFile) => record.uuid"
+                                size="small"
+                            />
+                            <Typography.Paragraph v-else type="secondary">
+                                No training files uploaded yet.
+                            </Typography.Paragraph>
+                        </div>
+                    </Tabs.TabPane>
                 </Tabs>
             </Card>
         </Spin>
 
         <Modal
             v-model:open="roleModalVisible"
-            title="Create Role"
-            ok-text="Create"
+            :title="roleWizardStep === 0 ? 'Create Role' : 'Upload Training Files'"
+            :ok-text="roleWizardStep === 0 ? 'Next' : 'Finish'"
             cancel-text="Cancel"
-            :ok-button-props="{ loading: creatingRole }"
-            @ok="createRole"
-            @cancel="resetRoleForm"
+            :ok-button-props="{ loading: roleWizardStep === 0 ? creatingRoleWizard : false }"
+            @ok="handleRoleWizardOk"
+            @cancel="closeRoleWizard"
         >
-            <div style="display: flex; flex-direction: column; gap: 0.75rem">
+            <Steps :current="roleWizardStep" size="small" style="margin-bottom: 1rem">
+                <Steps.Step title="Role Details" />
+                <Steps.Step title="Training Files" />
+            </Steps>
+
+            <div v-if="roleWizardStep === 0" style="display: flex; flex-direction: column; gap: 0.75rem">
                 <Input
                     v-model:value="createRoleForm.name"
                     placeholder="Role name"
                     :maxlength="100"
-                    @pressEnter="createRole"
+                    @pressEnter="handleRoleWizardOk"
                 />
                 <Input.TextArea
                     v-model:value="createRoleForm.description"
@@ -538,6 +908,116 @@ onMounted(async () => {
                     :maxlength="1000"
                 />
             </div>
+
+            <div v-else style="display: flex; flex-direction: column; gap: 0.75rem">
+                <Typography.Paragraph type="secondary" style="margin-bottom: 0">
+                    Upload optional training files for
+                    <strong>{{ createdRoleForWizard?.name }}</strong>
+                    . You can also do this later.
+                </Typography.Paragraph>
+
+                <Input.TextArea
+                    v-model:value="wizardFileDescription"
+                    placeholder="Optional file description"
+                    :rows="2"
+                    :maxlength="500"
+                />
+
+                <Upload.Dragger
+                    accept=".txt,.pdf,.md,.csv,.json,.docx,.doc"
+                    :before-upload="
+                        (file) => {
+                            handleRoleWizardFileSelected(file)
+                            return false
+                        }
+                    "
+                    :multiple="false"
+                    :auto-upload="false"
+                >
+                    <p class="ant-upload-drag-icon">
+                        <InboxOutlined />
+                    </p>
+                    <p class="ant-upload-text">Click or drag file to this area to select</p>
+                    <p class="ant-upload-hint">
+                        {{ wizardSelectedFile ? wizardSelectedFile.name : 'Single file upload' }}
+                    </p>
+                </Upload.Dragger>
+
+                <Button
+                    type="primary"
+                    :disabled="!wizardSelectedFile"
+                    :loading="wizardUploading"
+                    @click="uploadFileFromWizard"
+                >
+                    Upload Selected File
+                </Button>
+
+                <div v-if="wizardUploadedFiles.length > 0" class="uploaded-list">
+                    <Typography.Text strong>Uploaded in this setup:</Typography.Text>
+                    <List :data-source="wizardUploadedFiles" :bordered="false" size="small">
+                        <template #renderItem="{ item }">
+                            <List.Item>
+                                <List.Item.Meta :title="item.file_name" :description="item.role?.name" />
+                            </List.Item>
+                        </template>
+                    </List>
+                </div>
+            </div>
+        </Modal>
+
+        <Modal
+            v-model:open="uploadModalVisible"
+            title="Upload Training File"
+            ok-text="Upload"
+            cancel-text="Cancel"
+            :ok-button-props="{ loading: uploadingFile, disabled: !uploadRoleUuid || !uploadSelectedFile }"
+            @ok="handleUploadModalOk"
+            @cancel="uploadModalVisible = false"
+        >
+            <div style="display: flex; flex-direction: column; gap: 0.75rem">
+                <Typography.Text>
+                    Supported formats:
+                    <strong>txt, pdf, md, csv, json, docx, doc</strong>
+                    (Max 50MB)
+                </Typography.Text>
+
+                <div>
+                    <Typography.Text strong>Role</Typography.Text>
+                    <Select
+                        v-model:value="uploadRoleUuid"
+                        placeholder="Select a role"
+                        style="width: 100%"
+                        :options="Roles.map((role) => ({ label: role.name, value: role.uuid }))"
+                    />
+                </div>
+
+                <Input.TextArea
+                    v-model:value="uploadFileDescription"
+                    placeholder="Optional file description"
+                    :rows="2"
+                    :maxlength="500"
+                />
+
+                <Upload.Dragger
+                    accept=".txt,.pdf,.md,.csv,.json,.docx,.doc"
+                    :before-upload="
+                        (file) => {
+                            handleUploadModalFileSelected(file)
+                            return false
+                        }
+                    "
+                    :multiple="false"
+                    :auto-upload="false"
+                >
+                    <p class="ant-upload-drag-icon">
+                        <InboxOutlined />
+                    </p>
+                    <p class="ant-upload-text">Click or drag file to this area to select</p>
+                    <p class="ant-upload-hint">
+                        {{ uploadSelectedFile ? uploadSelectedFile.name : 'Single file upload' }}
+                    </p>
+                </Upload.Dragger>
+            </div>
         </Modal>
 
         <Modal
@@ -613,6 +1093,27 @@ onMounted(async () => {
     margin-bottom: 1rem;
 }
 
+.role-content {
+    width: 100%;
+    display: flex;
+    flex-direction: column;
+    gap: 0.75rem;
+}
+
+.role-head {
+    display: flex;
+    justify-content: space-between;
+    align-items: flex-start;
+    gap: 1rem;
+}
+
+.role-files {
+    background: #f8fafc;
+    border: 1px solid #e5e7eb;
+    border-radius: 8px;
+    padding: 0.75rem;
+}
+
 .white-tag {
     background-color: #ffffff !important;
     color: #000000 !important;
diff --git a/site/src/views/OrganizationView.vue b/site/src/views/OrganizationView.vue
index ee1a267..37bb94b 100644
--- a/site/src/views/OrganizationView.vue
+++ b/site/src/views/OrganizationView.vue
@@ -1,6 +1,7 @@
 <script setup lang="ts">
-import { ref, onMounted, computed, h, watch } from 'vue'
+import { ref, onMounted, onBeforeUnmount, computed, watch } from 'vue'
 import { useRouter, useRoute } from 'vue-router'
+import { useDocumentVisibility, useEventListener, useIntervalFn } from '@vueuse/core'
 import {
     Card,
     Typography,
@@ -11,15 +12,11 @@ import {
     message,
     Tag,
     Divider,
-    Upload,
     Modal,
-    Table,
-    Select,
 } from 'ant-design-vue'
 import { apiClient, isAxiosError, API } from '../router/api'
 import { useUserStore } from '../stores/userStore'
-import { InboxOutlined, DeleteOutlined } from '@ant-design/icons-vue'
-import type { Role, Organization, TrainingFile } from '../types/organization'
+import type { Role, Organization } from '../types/organization'
 
 const router = useRouter()
 const route = useRoute()
@@ -28,12 +25,13 @@ const organizationUuid = computed(() => String(route.params.organizationUuid ||
 const organization = ref<Organization | null>(null)
 const roles = ref<Role[]>([])
 const members = ref<Array<{ uuid: string; is_manager?: boolean }>>([])
-const trainingFiles = ref<TrainingFile[]>([])
 const loading = ref(false)
-const uploading = ref(false)
 const leavingOrganization = ref(false)
-const showUploadModal = ref(false)
+const rolePollingMs = 12000
 const auth = useUserStore()
+const visibility = useDocumentVisibility()
+const pollingInFlight = ref(false)
+let stopVisibilityListener: (() => void) | null = null
 
 const isManager = computed(() => {
     if (!auth.user || !organization.value) return false
@@ -154,12 +152,20 @@ const selectRole = async (roleUuid: string) => {
     try {
         await apiClient.post(API.roles.join(organization.value.uuid, roleUuid))
         message.success('Successfully joined role')
+
+        const joinedRole = roles.value.find((role) => role.uuid === roleUuid)
+        if (joinedRole) {
+            joinedRole.member_count = (joinedRole.member_count ?? 0) + 1
+        }
+
         if (!auth.userJoinedRoles.some((role) => role.uuid === roleUuid)) {
             auth.setJoinedRoles([
                 ...auth.userJoinedRoles,
                 roles.value.find((role) => role.uuid === roleUuid)!,
             ])
         }
+
+        await fetchRoles()
     } catch (error) {
         console.error('Failed to join role:', error)
         if (isAxiosError(error)) {
@@ -168,231 +174,59 @@ const selectRole = async (roleUuid: string) => {
     }
 }
 
-const fetchTrainingFiles = async () => {
-    if (!organization.value?.uuid) return
-    try {
-        const response = await apiClient.get<TrainingFile[]>(API.knowledge.trainingFiles.list(), {
-            params: { organization_uuid: organization.value.uuid },
-        })
-        trainingFiles.value = response.data
-    } catch (error) {
-        console.error('Failed to fetch training files:', error)
-    }
-}
-
-const beforeUpload = (file: File) => {
-    const allowedExtensions = ['txt', 'pdf', 'md', 'csv', 'json', 'docx', 'doc']
-    const fileExtension = file.name.split('.').pop()?.toLowerCase()
-
-    if (!fileExtension || !allowedExtensions.includes(fileExtension)) {
-        message.error(
-            `File type ".${fileExtension}" is not allowed. Allowed types: ${allowedExtensions.join(', ')}`,
-        )
-        return false
-    }
-
-    const maxSize = 50 * 1024 * 1024
-    if (file.size > maxSize) {
-        message.error(
-            `File size must not exceed 50MB. Current size: ${(file.size / 1024 / 1024).toFixed(2)}MB`,
-        )
-        return false
-    }
-
-    return false
-}
-
-const selectedFile = ref<File | null>(null)
-const fileDescription = ref('')
-const selectedRoleUuid = ref<string>('')
-
-const handleOpenUploadModal = () => {
-    if (!isManager.value) {
-        message.error('Only managers can upload training files')
-        return
-    }
-
-    if (roles.value.length === 0) {
-        message.error('No roles found for this organization. Create a role first in Manage Organization.')
-        return
-    }
-
-    showUploadModal.value = true
-}
-
-const handleFileSelected = (file: File) => {
-    selectedFile.value = file
-}
-
-const handleFileUploadClick = async () => {
-    if (!selectedFile.value) {
-        message.error('Please select a file to upload')
-        return
-    }
-    if (!selectedRoleUuid.value) {
-        message.error('Please select a role for this training file')
-        return
-    }
-
-    await handleFileUpload(selectedFile.value, fileDescription.value)
-    selectedFile.value = null
-    fileDescription.value = ''
-    selectedRoleUuid.value = ''
-}
-
-const handleFileUpload = async (file: File, description: string = '') => {
-    if (!organization.value?.uuid) {
-        message.error('Organization not loaded')
-        return
-    }
-
-    uploading.value = true
-    try {
-        const formData = new FormData()
-        formData.append('file', file)
-        formData.append('file_name', file.name)
-        formData.append('description', description)
-        if (selectedRoleUuid.value) {
-            formData.append('role_uuid', selectedRoleUuid.value)
-        }
-
-        const response = await apiClient.post<TrainingFile>(
-            API.knowledge.trainingFiles.list(),
-            formData,
-            {
-                headers: {
-                    'Content-Type': 'multipart/form-data',
-                },
-            },
-        )
-
-        message.success(`File "${file.name}" uploaded successfully`)
-        trainingFiles.value.unshift(response.data)
-        showUploadModal.value = false
-    } catch (error) {
-        console.error('Failed to upload file:', error)
-        if (isAxiosError(error)) {
-            const errorMsg =
-                error.response?.data?.error ||
-                error.response?.data?.file?.[0] ||
-                'Failed to upload file'
-            message.error(errorMsg)
-        } else {
-            message.error('Failed to upload file')
-        }
-    } finally {
-        uploading.value = false
-    }
-}
-
-const deleteFile = async (uuid: string, fileName: string) => {
-    if (!organization.value?.uuid) {
-        message.error('Organization not loaded')
-        return
-    }
-
-    Modal.confirm({
-        title: 'Delete File',
-        content: `Are you sure you want to delete "${fileName}"? This action cannot be undone.`,
-        okText: 'Delete',
-        okType: 'danger',
-        cancelText: 'Cancel',
-        onOk: async () => {
-            try {
-                await apiClient.delete(API.knowledge.trainingFiles.byId(uuid))
-                message.success('File deleted successfully')
-                trainingFiles.value = trainingFiles.value.filter((f) => f.uuid !== uuid)
-            } catch (error) {
-                console.error('Failed to delete file:', error)
-                message.error('Failed to delete file')
-            }
-        },
-    })
-}
-
-const formatFileSize = (bytes: number) => {
-    if (bytes === 0) return '0 Bytes'
-    const k = 1024
-    const sizes = ['Bytes', 'KB', 'MB', 'GB']
-    const i = Math.floor(Math.log(bytes) / Math.log(k))
-    return Math.round((bytes / Math.pow(k, i)) * 100) / 100 + ' ' + sizes[i]
-}
-
-const trainingFileColumns = [
-    {
-        title: 'File Name',
-        dataIndex: 'file_name',
-        key: 'file_name',
-    },
-    {
-        title: 'Uploaded By',
-        key: 'uploaded_by',
-        customRender: ({ record }: { record: TrainingFile }) => {
-            if (!record.uploaded_by) return '-'
-            const full_name = `${record.uploaded_by.first_name} ${record.uploaded_by.last_name}`
-            return full_name
-        },
-    },
-    {
-        title: 'Size',
-        dataIndex: 'file_size',
-        key: 'file_size',
-        customRender: ({ value }: { value: number }) => formatFileSize(value || 0),
-    },
-    {
-        title: 'Role',
-        key: 'role',
-        customRender: ({ record }: { record: TrainingFile }) => record.role?.name || '-',
-    },
-    {
-        title: 'Status',
-        dataIndex: 'status',
-        key: 'status',
-        customRender: ({ value }: { value: string }) => {
-            const statusMap: Record<string, { color: string; label: string }> = {
-                ingesting: { color: 'processing', label: 'Ingesting' },
-                chunked: { color: 'blue', label: 'Chunked' },
-                embedded: { color: 'success', label: 'Embedded' },
-                failed: { color: 'error', label: 'Failed' },
-            }
-            const status = statusMap[value] || { color: 'default', label: value }
-            return h(Tag, { color: status.color }, () => status.label)
-        },
-    },
-    {
-        title: 'Uploaded',
-        dataIndex: 'created_at',
-        key: 'created_at',
-        customRender: ({ value }: { value: string }) => new Date(value).toLocaleDateString(),
-    },
-    {
-        title: 'Action',
-        key: 'action',
-        customRender: ({ record }: { record: TrainingFile }) => {
-            if (isManager.value || auth.user?.uuid === record.uploaded_by?.uuid) {
-                return h(
-                    Button,
-                    {
-                        danger: true,
-                        size: 'small',
-                        icon: h(DeleteOutlined),
-                        onClick: () => deleteFile(record.uuid, record.file_name),
-                    },
-                    () => 'Delete',
-                )
-            }
-            return null
-        },
-    },
-]
-
 const loadOrganizationContext = async () => {
     await auth.fetchSession(true)
     await fetchOrganization()
     await fetchMembers()
     await fetchRoles()
     await fetchUserRoleMemberships()
-    await fetchTrainingFiles()
+}
+
+const canPollRoles = () => Boolean(organization.value?.uuid)
+
+const refreshRolesLive = async () => {
+    if (pollingInFlight.value || !canPollRoles()) return
+    pollingInFlight.value = true
+    try {
+        await Promise.all([fetchRoles(), fetchUserRoleMemberships()])
+    } finally {
+        pollingInFlight.value = false
+    }
+}
+
+const { pause: stopRolePolling, resume: resumeRolePolling } = useIntervalFn(
+    () => {
+        void refreshRolesLive()
+    },
+    rolePollingMs,
+    { immediate: false, immediateCallback: false },
+)
+
+const startRolePolling = () => {
+    stopRolePolling()
+    if (visibility.value !== 'visible' || !canPollRoles()) return
+    resumeRolePolling()
+}
+
+const bindVisibility = () => {
+    if (stopVisibilityListener) return
+    stopVisibilityListener = useEventListener(document, 'visibilitychange', () => {
+        if (visibility.value !== 'visible') {
+            stopRolePolling()
+            return
+        }
+
+        void refreshRolesLive()
+        if (canPollRoles()) {
+            resumeRolePolling()
+        }
+    })
+}
+
+const unbindVisibility = () => {
+    if (!stopVisibilityListener) return
+    stopVisibilityListener()
+    stopVisibilityListener = null
 }
 
 const leaveOrganization = () => {
@@ -436,16 +270,24 @@ const leaveOrganization = () => {
 
 onMounted(async () => {
     await loadOrganizationContext()
+    bindVisibility()
+    startRolePolling()
+})
+
+onBeforeUnmount(() => {
+    stopRolePolling()
+    unbindVisibility()
 })
 
 watch(
     () => organizationUuid.value,
     async (next, prev) => {
         if (!next || next === prev) return
+        stopRolePolling()
         roles.value = []
         members.value = []
-        trainingFiles.value = []
         await loadOrganizationContext()
+        startRolePolling()
     },
 )
 </script>
@@ -504,41 +346,6 @@ watch(
 
                 <Divider />
 
-                <Typography.Title :level="4" class="section-title">Training Files</Typography.Title>
-
-                <div style="margin-bottom: 1rem">
-                    <Button
-                        type="primary"
-                        :disabled="!isManager"
-                        @click="handleOpenUploadModal"
-                        style="margin-bottom: 1rem"
-                    >
-                        Upload Training File
-                    </Button>
-                    <Typography.Paragraph
-                        v-if="isManager && roles.length === 0"
-                        type="secondary"
-                        style="margin: 0.25rem 0 0"
-                    >
-                        Create a role in Manage Organization before uploading training files.
-                    </Typography.Paragraph>
-                </div>
-
-                <div v-if="trainingFiles.length > 0">
-                    <Table
-                        :columns="trainingFileColumns"
-                        :data-source="trainingFiles"
-                        :pagination="{ pageSize: 10 }"
-                        :row-key="(record: TrainingFile) => record.uuid"
-                        size="small"
-                    />
-                </div>
-                <Typography.Paragraph v-else type="secondary">
-                    No training files uploaded yet.
-                </Typography.Paragraph>
-
-                <Divider />
-
                 <Typography.Title :level="4" class="section-title">
                     Available Roles
                 </Typography.Title>
@@ -589,53 +396,6 @@ watch(
             </Card>
         </Spin>
 
-        <Modal
-            v-model:open="showUploadModal"
-            title="Upload Training File"
-            width="600px"
-            ok-text="Upload"
-            cancel-text="Cancel"
-            :ok-button-props="{ loading: uploading, disabled: !selectedFile || !selectedRoleUuid }"
-            @ok="handleFileUploadClick"
-            @cancel="showUploadModal = false"
-        >
-            <div style="display: flex; flex-direction: column; gap: 1rem">
-                <Typography.Text>
-                    Supported formats:
-                    <strong>txt, pdf, md, csv, json, docx, doc</strong>
-                    (Max 50MB)
-                </Typography.Text>
-                <div>
-                    <Typography.Text strong>Role</Typography.Text>
-                    <Select
-                        v-model:value="selectedRoleUuid"
-                        placeholder="Select a role"
-                        style="width: 100%"
-                        :options="roles.map((role) => ({ label: role.name, value: role.uuid }))"
-                    />
-                </div>
-                <Upload.Dragger
-                    accept=".txt,.pdf,.md,.csv,.json,.docx,.doc"
-                    :before-upload="
-                        (file) => {
-                            beforeUpload(file)
-                            handleFileSelected(file)
-                            return false
-                        }
-                    "
-                    :multiple="false"
-                    :auto-upload="false"
-                >
-                    <p class="ant-upload-drag-icon">
-                        <InboxOutlined />
-                    </p>
-                    <p class="ant-upload-text">Click or drag file to this area to upload</p>
-                    <p class="ant-upload-hint">
-                        {{ selectedFile ? selectedFile.name : 'Single file upload' }}
-                    </p>
-                </Upload.Dragger>
-            </div>
-        </Modal>
     </div>
 </template>