diff --git a/.changeset/soft-apples-play.md b/.changeset/soft-apples-play.md
new file mode 100644
index 0000000000..6bf8a359b8
--- /dev/null
+++ b/.changeset/soft-apples-play.md
@@ -0,0 +1,4 @@
+---
+---
+
+Fix profile completion goal to only show for paid members, handle personal workspaces
diff --git a/.changeset/wicked-memes-act.md b/.changeset/wicked-memes-act.md
new file mode 100644
index 0000000000..7596795353
--- /dev/null
+++ b/.changeset/wicked-memes-act.md
@@ -0,0 +1,4 @@
+---
+---
+
+Admin collaboration features for outreach: add insight button, year reference cleanup, vendor membership goal, admin nudge/override
diff --git a/.gitignore b/.gitignore
index a9d73295d5..b99871c163 100644
--- a/.gitignore
+++ b/.gitignore
@@ -17,6 +17,7 @@ server/node_modules
 
 # Misc
 .DS_Store
+cookies.txt
 .conductor_port
 .env.local
 .env.development.local
diff --git a/server/public/admin-users.html b/server/public/admin-users.html
index 32a725bab8..8392505901 100644
--- a/server/public/admin-users.html
+++ b/server/public/admin-users.html
@@ -895,6 +895,83 @@ <h2 id="contextModalTitle">Member Context</h2>
     </div>
   </div>
 
+  <!-- Add Insight Modal -->
+  <div id="addInsightModal" class="modal-backdrop hidden" onclick="closeAddInsightModal(event)">
+    <div class="modal-content" style="max-width: 500px;" onclick="event.stopPropagation()">
+      <div class="modal-header">
+        <h2>Add Insight</h2>
+        <button class="modal-close" onclick="closeAddInsightModal()">&times;</button>
+      </div>
+      <div class="modal-body">
+        <form id="addInsightForm" onsubmit="submitInsight(event)">
+          <input type="hidden" id="insightSlackUserId" />
+
+          <div class="form-group" style="margin-bottom: var(--space-4);">
+            <label for="insightType" style="display: block; font-weight: var(--font-medium); margin-bottom: var(--space-2);">Insight Type</label>
+            <select id="insightType" required style="width: 100%; padding: var(--space-2); border: 1px solid var(--color-gray-300); border-radius: var(--radius-sm);">
+              <option value="">Select type...</option>
+            </select>
+          </div>
+
+          <div class="form-group" style="margin-bottom: var(--space-4);">
+            <label for="insightValue" style="display: block; font-weight: var(--font-medium); margin-bottom: var(--space-2);">Value</label>
+            <textarea id="insightValue" required rows="3" placeholder="What do you know about this person?" style="width: 100%; padding: var(--space-2); border: 1px solid var(--color-gray-300); border-radius: var(--radius-sm); resize: vertical;"></textarea>
+          </div>
+
+          <div class="form-group" style="margin-bottom: var(--space-4);">
+            <label for="insightConfidence" style="display: block; font-weight: var(--font-medium); margin-bottom: var(--space-2);">Confidence</label>
+            <select id="insightConfidence" style="width: 100%; padding: var(--space-2); border: 1px solid var(--color-gray-300); border-radius: var(--radius-sm);">
+              <option value="high">High - Directly told to me</option>
+              <option value="medium" selected>Medium - Inferred from context</option>
+              <option value="low">Low - Guess/assumption</option>
+            </select>
+          </div>
+
+          <div style="display: flex; gap: var(--space-2); justify-content: flex-end;">
+            <button type="button" onclick="closeAddInsightModal()" class="btn btn-secondary">Cancel</button>
+            <button type="submit" class="btn btn-primary" id="submitInsightBtn">Add Insight</button>
+          </div>
+        </form>
+      </div>
+    </div>
+  </div>
+
+  <!-- Nudge/Override Modal -->
+  <div id="nudgeModal" class="modal-backdrop hidden" onclick="closeNudgeModal(event)">
+    <div class="modal-content" style="max-width: 550px;" onclick="event.stopPropagation()">
+      <div class="modal-header">
+        <h2>Different Approach</h2>
+        <button class="modal-close" onclick="closeNudgeModal()">&times;</button>
+      </div>
+      <div class="modal-body">
+        <input type="hidden" id="nudgeSlackUserId" />
+        <input type="hidden" id="nudgeGoalId" />
+
+        <div id="nudgeGoalInfo" style="background: var(--color-primary-50); border-radius: var(--radius-sm); padding: var(--space-3); margin-bottom: var(--space-4);">
+          <div style="font-weight: var(--font-medium); margin-bottom: var(--space-1);" id="nudgeGoalName">Loading...</div>
+          <div style="font-size: var(--text-sm); color: var(--color-text-secondary);" id="nudgeGoalDescription"></div>
+        </div>
+
+        <div class="form-group" style="margin-bottom: var(--space-4);">
+          <label for="nudgeContext" style="display: block; font-weight: var(--font-medium); margin-bottom: var(--space-2);">Additional Context (optional)</label>
+          <textarea id="nudgeContext" rows="3" placeholder="Share what you know about this person that might help personalize the message... (this will be saved as an insight)" style="width: 100%; padding: var(--space-2); border: 1px solid var(--color-gray-300); border-radius: var(--radius-sm); resize: vertical;"></textarea>
+          <p style="font-size: var(--text-xs); color: var(--color-text-muted); margin-top: var(--space-1);">If provided, this will be recorded as an "admin_context" insight for future reference.</p>
+        </div>
+
+        <div id="nudgeMessagePreview" style="margin-bottom: var(--space-4); display: none;">
+          <label style="display: block; font-weight: var(--font-medium); margin-bottom: var(--space-2);">Message Preview</label>
+          <div style="background: white; border: 1px solid var(--color-gray-200); border-radius: var(--radius-sm); padding: var(--space-3); font-size: var(--text-sm); white-space: pre-wrap; max-height: 150px; overflow-y: auto;" id="nudgeMessageText"></div>
+        </div>
+
+        <div style="display: flex; gap: var(--space-2); justify-content: flex-end; flex-wrap: wrap;">
+          <button type="button" onclick="closeNudgeModal()" class="btn btn-secondary">Cancel</button>
+          <button type="button" onclick="saveNudgeAsInsight()" class="btn btn-secondary" id="saveNudgeBtn" style="display: none;">Just Save Context</button>
+          <button type="button" onclick="sendNudgeOutreach()" class="btn btn-primary" id="sendNudgeBtn">Send with This Goal</button>
+        </div>
+      </div>
+    </div>
+  </div>
+
   <script>
     let allUsers = [];
     let allGroups = [];
@@ -1799,11 +1876,12 @@ <h2 id="contextModalTitle">Member Context</h2>
           html += '<div style="font-size: var(--text-xs); color: var(--color-text-muted); margin-bottom: var(--space-2);">Message Preview:</div>';
           html += `<div style="background: white; border: 1px solid var(--color-gray-200); border-radius: var(--radius-sm); padding: var(--space-3); font-size: var(--text-sm); white-space: pre-wrap; max-height: 200px; overflow-y: auto;">${escapeHtml(context.planner.message_preview)}</div>`;
 
-          // Send button
+          // Send button and different approach link
           if (slackUserId && !context.outreach?.opted_out) {
-            html += `<div style="margin-top: var(--space-3); display: flex; gap: var(--space-2); align-items: center;">
+            html += `<div style="margin-top: var(--space-3); display: flex; gap: var(--space-2); align-items: center; flex-wrap: wrap;">
               <button onclick="sendOutreach('${slackUserId}')" class="btn btn-primary btn-small" id="sendOutreachBtn-${slackUserId}">Send This Message</button>
               <span style="font-size: var(--text-xs); color: var(--color-text-muted);">via Slack DM</span>
+              <a href="#" onclick="openNudgeModal('${slackUserId}', ${action.goal_id}); return false;" style="font-size: var(--text-xs); color: var(--color-brand); margin-left: auto;">Different approach?</a>
             </div>`;
           }
           html += '</div>';
@@ -1811,9 +1889,12 @@ <h2 id="contextModalTitle">Member Context</h2>
 
         if (context.planner.alternative_goals && context.planner.alternative_goals.length > 0) {
           html += '<div style="margin-top: var(--space-3); padding-top: var(--space-2); border-top: 1px solid var(--color-gray-200);">';
-          html += '<div style="font-size: var(--text-xs); color: var(--color-text-muted); margin-bottom: var(--space-1);">Alternative goals:</div>';
-          html += context.planner.alternative_goals.map(g => `<span style="display: inline-block; padding: 2px var(--space-2); background: var(--color-gray-100); border-radius: var(--radius-sm); font-size: var(--text-xs); margin-right: var(--space-1);">${escapeHtml(g.name)}</span>`).join('');
-          html += '</div>';
+          html += '<div style="font-size: var(--text-xs); color: var(--color-text-muted); margin-bottom: var(--space-2);">Alternative goals (click to use instead):</div>';
+          html += '<div style="display: flex; flex-wrap: wrap; gap: var(--space-1);">';
+          html += context.planner.alternative_goals.map(g =>
+            `<button onclick="openNudgeModal('${slackUserId}', ${g.id})" style="display: inline-block; padding: 4px var(--space-2); background: var(--color-gray-100); border: 1px solid var(--color-gray-200); border-radius: var(--radius-sm); font-size: var(--text-xs); cursor: pointer; transition: all 0.15s;" onmouseover="this.style.background='var(--color-primary-50)';this.style.borderColor='var(--color-brand)'" onmouseout="this.style.background='var(--color-gray-100)';this.style.borderColor='var(--color-gray-200)'">${escapeHtml(g.name)}</button>`
+          ).join('');
+          html += '</div></div>';
         }
         html += '</div>';
       } else if (context.planner && !context.planner.recommended_action) {
@@ -1826,19 +1907,6 @@ <h2 id="contextModalTitle">Member Context</h2>
           html += '<div style="font-size: var(--text-sm); color: var(--color-text-muted); font-style: italic;">No action recommended at this time.</div>';
         }
         html += '</div>';
-      } else if (context.addie_goal) {
-        // Fallback to legacy addie_goal if no planner data
-        html += '<div class="context-section" style="background: var(--color-primary-50); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4);">';
-        html += '<h3 style="margin-bottom: var(--space-2);">Addie\'s Goal</h3>';
-        html += `<div style="margin-bottom: var(--space-2);">
-          <span class="goal-badge goal-${context.addie_goal.goal_key}" style="font-size: var(--text-sm); padding: var(--space-1) var(--space-3);">
-            ${escapeHtml(context.addie_goal.goal_name || formatGoalKey(context.addie_goal.goal_key))}
-          </span>
-        </div>`;
-        if (context.addie_goal.reasoning) {
-          html += `<p style="font-size: var(--text-sm); color: var(--color-text-secondary); margin: 0;">${escapeHtml(context.addie_goal.reasoning)}</p>`;
-        }
-        html += '</div>';
       }
 
       // Capabilities Section - What has this member done?
@@ -1986,15 +2054,19 @@ <h2 id="contextModalTitle">Member Context</h2>
 
       // Insights Section - From collected member insights
       // Strategic insights are highlighted at top, others shown below
+      const slackUserIdForInsight = context.slack_user?.slack_user_id;
       if (context.insights && context.insights.length > 0) {
-        const strategicTypes = ['plans_2026', 'membership_goals', 'challenges', 'feedback', 'satisfaction', 'use_case'];
+        const strategicTypes = ['plans_2026', 'membership_goals', 'challenges', 'feedback', 'satisfaction', 'use_case', 'admin_context'];
         const strategicInsights = context.insights.filter(i => strategicTypes.includes(i.type_name));
         const otherInsights = context.insights.filter(i => !strategicTypes.includes(i.type_name));
 
         // Strategic insights get prominent display
         if (strategicInsights.length > 0) {
           html += '<div class="context-section" style="background: linear-gradient(135deg, var(--color-success-50), var(--color-gray-50)); border-left: 4px solid var(--color-success-600); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4);">';
-          html += '<h3 style="margin-bottom: var(--space-3);">Strategic Insights</h3>';
+          html += `<div style="display: flex; justify-content: space-between; align-items: center; margin-bottom: var(--space-3);">
+            <h3 style="margin: 0;">Strategic Insights</h3>
+            ${slackUserIdForInsight ? `<button onclick="openAddInsightModal('${slackUserIdForInsight}')" class="btn btn-small" style="font-size: var(--text-xs);">+ Add Insight</button>` : ''}
+          </div>`;
           html += '<div style="display: grid; gap: var(--space-3);">';
           strategicInsights.forEach(insight => {
             const label = formatInsightLabel(insight.type_name);
@@ -2019,6 +2091,12 @@ <h2 id="contextModalTitle">Member Context</h2>
           });
           html += '</div></div>';
         }
+      } else if (slackUserIdForInsight) {
+        // No insights yet - show add button
+        html += '<div class="context-section" style="background: var(--color-gray-50); border-radius: var(--radius-md); padding: var(--space-4); margin-bottom: var(--space-4); text-align: center;">';
+        html += '<p style="color: var(--color-text-muted); margin-bottom: var(--space-3);">No insights recorded yet</p>';
+        html += `<button onclick="openAddInsightModal('${slackUserIdForInsight}')" class="btn btn-primary btn-small">+ Add First Insight</button>`;
+        html += '</div>';
       }
 
       // Recent Conversations Section (from new threads API)
@@ -2155,10 +2233,334 @@ <h3 style="margin: 0;">Addie Home Preview</h3>
       </div>`;
     }
 
+    // =========================================================================
+    // Add Insight Modal Functions
+    // =========================================================================
+
+    let insightTypes = [];
+    let currentInsightSlackUserId = null;
+
+    async function loadInsightTypes() {
+      if (insightTypes.length > 0) return; // Already loaded
+      try {
+        const response = await fetch('/api/admin/insight-types');
+        if (response.ok) {
+          const types = await response.json();
+          insightTypes = types.filter(t => t.is_active);
+          populateInsightTypeDropdown();
+        }
+      } catch (error) {
+        console.error('Error loading insight types:', error);
+      }
+    }
+
+    function populateInsightTypeDropdown() {
+      const select = document.getElementById('insightType');
+      select.innerHTML = '<option value="">Select type...</option>';
+
+      // Group by strategic vs other
+      const strategicTypes = ['plans_2026', 'membership_goals', 'challenges', 'feedback', 'satisfaction', 'use_case', 'admin_context'];
+      const strategic = insightTypes.filter(t => strategicTypes.includes(t.name));
+      const other = insightTypes.filter(t => !strategicTypes.includes(t.name));
+
+      if (strategic.length > 0) {
+        const group = document.createElement('optgroup');
+        group.label = 'Strategic Insights';
+        strategic.forEach(type => {
+          const option = document.createElement('option');
+          option.value = type.id;
+          option.textContent = type.name.replace(/_/g, ' ').replace(/\b\w/g, c => c.toUpperCase());
+          if (type.description) option.title = type.description;
+          group.appendChild(option);
+        });
+        select.appendChild(group);
+      }
+
+      if (other.length > 0) {
+        const group = document.createElement('optgroup');
+        group.label = 'Other Insights';
+        other.forEach(type => {
+          const option = document.createElement('option');
+          option.value = type.id;
+          option.textContent = type.name.replace(/_/g, ' ').replace(/\b\w/g, c => c.toUpperCase());
+          if (type.description) option.title = type.description;
+          group.appendChild(option);
+        });
+        select.appendChild(group);
+      }
+    }
+
+    async function openAddInsightModal(slackUserId) {
+      currentInsightSlackUserId = slackUserId;
+      document.getElementById('insightSlackUserId').value = slackUserId;
+      document.getElementById('insightValue').value = '';
+      document.getElementById('insightConfidence').value = 'medium';
+
+      await loadInsightTypes();
+      document.getElementById('addInsightModal').classList.remove('hidden');
+      document.getElementById('insightType').focus();
+    }
+
+    function closeAddInsightModal(event) {
+      if (event && event.target !== event.currentTarget) return;
+      document.getElementById('addInsightModal').classList.add('hidden');
+      currentInsightSlackUserId = null;
+    }
+
+    async function submitInsight(event) {
+      event.preventDefault();
+
+      const slackUserId = document.getElementById('insightSlackUserId').value;
+      const typeId = document.getElementById('insightType').value;
+      const value = document.getElementById('insightValue').value.trim();
+      const confidence = document.getElementById('insightConfidence').value;
+
+      if (!slackUserId || !typeId || !value) {
+        alert('Please fill in all required fields');
+        return;
+      }
+
+      const btn = document.getElementById('submitInsightBtn');
+      const originalText = btn.textContent;
+      btn.textContent = 'Adding...';
+      btn.disabled = true;
+
+      try {
+        const response = await fetch('/api/admin/insights', {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          body: JSON.stringify({
+            slack_user_id: slackUserId,
+            insight_type_id: parseInt(typeId),
+            value: value,
+            confidence: confidence,
+          }),
+        });
+
+        if (!response.ok) {
+          const error = await response.json();
+          throw new Error(error.error || 'Failed to add insight');
+        }
+
+        closeAddInsightModal();
+
+        // Refresh the context modal to show the new insight
+        const user = allUsers.find(u => u.slack_user_id === slackUserId);
+        if (user) {
+          showContextModal(user.id || slackUserId, user.display_name || user.email || 'User');
+        }
+      } catch (error) {
+        alert('Error adding insight: ' + error.message);
+      } finally {
+        btn.textContent = originalText;
+        btn.disabled = false;
+      }
+    }
+
+    // =========================================================================
+    // NUDGE/OVERRIDE MODAL FUNCTIONS
+    // =========================================================================
+
+    let currentNudgeSlackUserId = null;
+    let currentNudgeGoalId = null;
+    let currentNudgeGoal = null;
+
+    async function openNudgeModal(slackUserId, goalId) {
+      currentNudgeSlackUserId = slackUserId;
+      currentNudgeGoalId = goalId;
+
+      // Set hidden fields
+      document.getElementById('nudgeSlackUserId').value = slackUserId;
+      document.getElementById('nudgeGoalId').value = goalId;
+
+      // Reset form
+      document.getElementById('nudgeContext').value = '';
+      document.getElementById('nudgeGoalName').textContent = 'Loading...';
+      document.getElementById('nudgeGoalDescription').textContent = '';
+      document.getElementById('nudgeMessagePreview').style.display = 'none';
+
+      // Show modal
+      document.getElementById('nudgeModal').classList.remove('hidden');
+
+      // Fetch goal details
+      try {
+        const response = await fetch(`/api/admin/outbound/goals/${goalId}`);
+        if (!response.ok) throw new Error('Failed to load goal');
+
+        currentNudgeGoal = await response.json();
+        document.getElementById('nudgeGoalName').textContent = currentNudgeGoal.name;
+        document.getElementById('nudgeGoalDescription').textContent = currentNudgeGoal.description || '';
+
+        // Build and show message preview
+        const user = allUsers.find(u => u.slack_user_id === slackUserId);
+        const displayName = user?.display_name || user?.slack_real_name || 'there';
+        const companyName = user?.company_name || 'your company';
+
+        // Simple template substitution for preview
+        let messagePreview = currentNudgeGoal.message_template || '';
+        messagePreview = messagePreview.replace(/\{\{user_name\}\}/g, displayName);
+        messagePreview = messagePreview.replace(/\{\{company_name\}\}/g, companyName);
+
+        document.getElementById('nudgeMessageText').textContent = messagePreview;
+        document.getElementById('nudgeMessagePreview').style.display = 'block';
+
+        // Show "Just Save Context" button if context field has focus
+        // Remove existing listener first to prevent accumulation on repeated modal opens
+        const nudgeContextEl = document.getElementById('nudgeContext');
+        nudgeContextEl.removeEventListener('input', toggleSaveContextButton);
+        nudgeContextEl.addEventListener('input', toggleSaveContextButton);
+      } catch (error) {
+        console.error('Error loading goal:', error);
+        document.getElementById('nudgeGoalName').textContent = 'Goal #' + goalId;
+        document.getElementById('nudgeGoalDescription').textContent = 'Could not load goal details';
+      }
+    }
+
+    function toggleSaveContextButton() {
+      const hasContext = document.getElementById('nudgeContext').value.trim().length > 0;
+      document.getElementById('saveNudgeBtn').style.display = hasContext ? 'inline-flex' : 'none';
+    }
+
+    function closeNudgeModal(event) {
+      if (event && event.target !== event.currentTarget) return;
+      document.getElementById('nudgeModal').classList.add('hidden');
+      currentNudgeSlackUserId = null;
+      currentNudgeGoalId = null;
+      currentNudgeGoal = null;
+    }
+
+    async function sendNudgeOutreach() {
+      if (!currentNudgeSlackUserId || !currentNudgeGoalId) {
+        alert('Missing user or goal information');
+        return;
+      }
+
+      const adminContext = document.getElementById('nudgeContext').value.trim();
+
+      if (!confirm(`Send outreach to this user using the "${currentNudgeGoal?.name || 'selected'}" goal? This will DM them via Slack.`)) {
+        return;
+      }
+
+      const btn = document.getElementById('sendNudgeBtn');
+      const originalText = btn.textContent;
+      btn.textContent = 'Sending...';
+      btn.disabled = true;
+
+      try {
+        const response = await fetch('/api/admin/outreach/send-with-goal', {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          body: JSON.stringify({
+            slack_user_id: currentNudgeSlackUserId,
+            goal_id: currentNudgeGoalId,
+            admin_context: adminContext || undefined,
+          }),
+        });
+
+        if (!response.ok) {
+          const error = await response.json();
+          throw new Error(error.error || 'Failed to send outreach');
+        }
+
+        const data = await response.json();
+
+        if (data.success) {
+          btn.textContent = 'Sent!';
+          btn.classList.remove('btn-primary');
+          btn.classList.add('btn-success');
+
+          // Close modal and refresh context after a moment
+          setTimeout(() => {
+            closeNudgeModal();
+            // Refresh context modal
+            const user = allUsers.find(u => u.slack_user_id === currentNudgeSlackUserId);
+            if (user) {
+              showContextModal(user.id || currentNudgeSlackUserId, user.display_name || user.email || 'User');
+            }
+          }, 1000);
+        } else {
+          throw new Error(data.error || 'Unknown error');
+        }
+      } catch (error) {
+        alert('Error sending outreach: ' + error.message);
+        btn.textContent = originalText;
+        btn.disabled = false;
+      }
+    }
+
+    async function saveNudgeAsInsight() {
+      const adminContext = document.getElementById('nudgeContext').value.trim();
+
+      if (!adminContext) {
+        alert('Please enter some context to save');
+        return;
+      }
+
+      if (!currentNudgeSlackUserId) {
+        alert('Missing user information');
+        return;
+      }
+
+      const btn = document.getElementById('saveNudgeBtn');
+      const originalText = btn.textContent;
+      btn.textContent = 'Saving...';
+      btn.disabled = true;
+
+      try {
+        // First get the admin_context insight type
+        const typesResponse = await fetch('/api/admin/insight-types');
+        if (!typesResponse.ok) throw new Error('Failed to load insight types');
+
+        const types = await typesResponse.json();
+        const adminContextType = types.find(t => t.name === 'admin_context');
+
+        if (!adminContextType) {
+          throw new Error('admin_context insight type not found');
+        }
+
+        // Save the insight
+        const response = await fetch('/api/admin/insights', {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          body: JSON.stringify({
+            slack_user_id: currentNudgeSlackUserId,
+            insight_type_id: adminContextType.id,
+            value: adminContext,
+            confidence: 'high',
+          }),
+        });
+
+        if (!response.ok) {
+          const error = await response.json();
+          throw new Error(error.error || 'Failed to save insight');
+        }
+
+        btn.textContent = 'Saved!';
+        btn.classList.remove('btn-secondary');
+        btn.classList.add('btn-success');
+
+        // Close modal and refresh context after a moment
+        setTimeout(() => {
+          closeNudgeModal();
+          // Refresh context modal
+          const user = allUsers.find(u => u.slack_user_id === currentNudgeSlackUserId);
+          if (user) {
+            showContextModal(user.id || currentNudgeSlackUserId, user.display_name || user.email || 'User');
+          }
+        }, 1000);
+      } catch (error) {
+        alert('Error saving insight: ' + error.message);
+        btn.textContent = originalText;
+        btn.disabled = false;
+      }
+    }
+
     // Close modal on Escape key
     document.addEventListener('keydown', function(e) {
       if (e.key === 'Escape') {
         closeContextModal();
+        closeAddInsightModal();
+        closeNudgeModal();
       }
     });
 
diff --git a/server/src/addie/services/outbound-planner.ts b/server/src/addie/services/outbound-planner.ts
index 7ca4174cab..cdfcc79163 100644
--- a/server/src/addie/services/outbound-planner.ts
+++ b/server/src/addie/services/outbound-planner.ts
@@ -210,15 +210,16 @@ export class OutboundPlanner {
       }
     }
 
-    // PRIORITY 2: Profile completion (critical setup step)
-    if (caps && !caps.profile_complete) {
+    // PRIORITY 2: Profile completion (only for paid members - profiles are only visible to members)
+    // Skip for personal workspaces since those aren't real company profiles
+    if (caps && !caps.profile_complete && ctx.user.is_member && !ctx.company?.is_personal_workspace) {
       const profileGoal = goals.find(g =>
         g.name.toLowerCase().includes('profile') && g.category === 'admin'
       );
       if (profileGoal) {
         return {
           goal: profileGoal,
-          reason: 'Profile not complete - key capability to unlock',
+          reason: 'Profile not complete - visible to other members once set up',
           priority_score: 85,
           alternative_goals: goals.filter(g => g.id !== profileGoal.id).slice(0, 3),
           decision_method: 'rule_match',
@@ -226,7 +227,25 @@ export class OutboundPlanner {
       }
     }
 
-    // PRIORITY 3: Working group discovery (for engaged users with none)
+    // PRIORITY 3: Vendor membership (tech companies benefit from profile visibility)
+    // Only for non-members at vendor-type companies
+    const vendorTypes = ['adtech', 'ai', 'data'];
+    if (ctx.user.is_mapped && !ctx.user.is_member && ctx.company?.type && vendorTypes.includes(ctx.company.type)) {
+      const vendorGoal = goals.find(g =>
+        g.name.toLowerCase().includes('vendor') && g.category === 'invitation'
+      );
+      if (vendorGoal) {
+        return {
+          goal: vendorGoal,
+          reason: 'Tech vendor not a member - profiles visible to members would help their business',
+          priority_score: 75,
+          alternative_goals: goals.filter(g => g.id !== vendorGoal.id).slice(0, 3),
+          decision_method: 'rule_match',
+        };
+      }
+    }
+
+    // PRIORITY 4: Working group discovery (for engaged users with none)
     if (caps && caps.account_linked && caps.working_group_count === 0 && caps.slack_message_count_30d > 5) {
       const wgGoal = goals.find(g =>
         g.name.toLowerCase().includes('working group') && g.category === 'education'
@@ -242,7 +261,7 @@ export class OutboundPlanner {
       }
     }
 
-    // PRIORITY 4: Re-engagement for dormant users
+    // PRIORITY 5: Re-engagement for dormant users
     if (caps && caps.last_active_days_ago !== null && caps.last_active_days_ago > 30) {
       const reengageGoal = goals.find(g =>
         g.name.toLowerCase().includes('re-engage') || g.name.toLowerCase().includes('dormant')
@@ -433,8 +452,13 @@ Respond ONLY with valid JSON (no markdown code blocks):
   buildMessage(goal: OutreachGoal, ctx: PlannerContext, linkUrl?: string): string {
     let message = goal.message_template;
 
+    // Extract first name from display name (e.g., "Julie Lorin" -> "Julie")
+    // Handle edge cases: empty strings, single-char names (like "J."), etc.
+    const rawFirstName = ctx.user.display_name?.trim().split(' ')[0];
+    const firstName = rawFirstName && rawFirstName.length > 1 ? rawFirstName : 'there';
+
     // Replace placeholders
-    message = message.replace(/\{\{user_name\}\}/g, ctx.user.display_name ?? 'there');
+    message = message.replace(/\{\{user_name\}\}/g, firstName);
     message = message.replace(/\{\{company_name\}\}/g, ctx.company?.name ?? 'your company');
     message = message.replace(/\{\{link_url\}\}/g, linkUrl ?? '');
 
diff --git a/server/src/addie/services/proactive-outreach.ts b/server/src/addie/services/proactive-outreach.ts
index f0f8d5fc6a..382427a306 100644
--- a/server/src/addie/services/proactive-outreach.ts
+++ b/server/src/addie/services/proactive-outreach.ts
@@ -172,14 +172,16 @@ async function buildPlannerContext(candidate: OutreachCandidate): Promise<Planne
     canContactUser(candidate.slack_user_id),
   ]);
 
-  // Get company info if user is mapped
+  // Get company info and membership status if user is mapped
   let company: PlannerContext['company'] | undefined;
+  let isMember = false;
   if (candidate.workos_user_id) {
     const orgResult = await query<{
       name: string;
       company_types: string[] | null;
+      subscription_status: string | null;
     }>(
-      `SELECT o.name, o.company_types
+      `SELECT o.name, o.company_types, o.subscription_status
        FROM organization_memberships om
        JOIN organizations o ON o.workos_organization_id = om.workos_organization_id
        WHERE om.workos_user_id = $1
@@ -188,10 +190,14 @@ async function buildPlannerContext(candidate: OutreachCandidate): Promise<Planne
     );
     if (orgResult.rows[0]) {
       const org = orgResult.rows[0];
+      const isPersonalWorkspace = org.name.toLowerCase().endsWith("'s workspace") ||
+                                  org.name.toLowerCase().endsWith("'s workspace");
       company = {
-        name: org.name,
+        name: isPersonalWorkspace ? 'your account' : org.name,
         type: org.company_types?.[0] ?? 'unknown',
+        is_personal_workspace: isPersonalWorkspace,
       };
+      isMember = org.subscription_status === 'active';
     }
   }
 
@@ -206,6 +212,7 @@ async function buildPlannerContext(candidate: OutreachCandidate): Promise<Planne
       workos_user_id: candidate.workos_user_id ?? undefined,
       display_name: candidate.slack_display_name ?? candidate.slack_real_name ?? undefined,
       is_mapped: !!candidate.workos_user_id,
+      is_member: isMember,
       engagement_score: engagementScore,
       insights: insights.map(i => ({
         type: i.insight_type_name ?? 'unknown',
@@ -717,6 +724,170 @@ export async function manualOutreach(
   return outreachResult;
 }
 
+/**
+ * Manual outreach with a specific goal (admin override)
+ *
+ * Allows admins to send outreach using a specific goal instead of the planner's recommendation.
+ * Optionally records admin context as an insight before sending.
+ *
+ * @param slackUserId - Target user's Slack ID
+ * @param goalId - Specific goal ID to use
+ * @param adminContext - Optional context from admin to record as insight
+ * @param triggeredBy - Admin who triggered the outreach
+ */
+export async function manualOutreachWithGoal(
+  slackUserId: string,
+  goalId: number,
+  adminContext?: string,
+  triggeredBy?: { id: string; name: string; email: string }
+): Promise<OutreachResult> {
+  const planner = getOutboundPlanner();
+
+  // Look up user
+  const result = await query<SlackUserMapping>(
+    `SELECT * FROM slack_user_mappings WHERE slack_user_id = $1`,
+    [slackUserId]
+  );
+
+  if (result.rows.length === 0) {
+    return { success: false, error: 'User not found' };
+  }
+
+  const user = result.rows[0];
+
+  // Get the specific goal
+  const goal = await outboundDb.getGoal(goalId);
+  if (!goal) {
+    return { success: false, error: 'Goal not found' };
+  }
+
+  // Record admin context as insight if provided
+  if (adminContext && adminContext.trim()) {
+    try {
+      // Find or create admin_context insight type
+      const adminContextType = await insightsDb.getInsightTypeByName('admin_context');
+      if (adminContextType) {
+        await insightsDb.addInsight({
+          slack_user_id: slackUserId,
+          insight_type_id: adminContextType.id,
+          value: adminContext.trim(),
+          confidence: 'high',
+          source_type: 'manual',
+        });
+        logger.info({
+          slackUserId,
+          adminId: triggeredBy?.id,
+          contextLength: adminContext.length,
+        }, 'Recorded admin context as insight');
+      }
+    } catch (error) {
+      // Don't fail outreach if insight recording fails
+      logger.warn({ error, slackUserId }, 'Failed to record admin context insight');
+    }
+  }
+
+  // Build context for message generation
+  const candidate: OutreachCandidate = {
+    slack_user_id: user.slack_user_id,
+    slack_email: user.slack_email,
+    slack_display_name: user.slack_display_name,
+    slack_real_name: user.slack_real_name,
+    workos_user_id: user.workos_user_id,
+    last_outreach_at: user.last_outreach_at,
+    priority: calculatePriority(user),
+  };
+  const ctx = await buildPlannerContext(candidate);
+
+  // Build the message from the goal template
+  const linkUrl = `https://agenticadvertising.org/auth/login?slack_user_id=${encodeURIComponent(slackUserId)}`;
+  const message = planner.buildMessage(goal, ctx, linkUrl);
+
+  // DRY_RUN mode: log but don't send
+  if (OUTREACH_MODE === 'dry_run') {
+    logger.info({
+      mode: 'dry_run',
+      candidate: slackUserId,
+      goal: goal.name,
+      goalId: goal.id,
+      triggeredBy: triggeredBy?.id,
+      hasAdminContext: !!adminContext,
+      message: message.substring(0, 100) + '...',
+    }, 'DRY RUN: Would send admin-override outreach');
+    return { success: true };
+  }
+
+  // Open DM channel
+  const channelId = await openDmChannel(slackUserId);
+  if (!channelId) {
+    return { success: false, error: 'Failed to open DM channel' };
+  }
+
+  // Send message
+  const messageTs = await sendDmMessage(channelId, message);
+  if (!messageTs) {
+    return { success: false, error: 'Failed to send DM message' };
+  }
+
+  // Map goal category to outreach type
+  const outreachType: OutreachType = goal.category === 'admin' ? 'account_link'
+    : goal.category === 'information' ? 'insight_goal'
+    : 'custom';
+
+  // Record outreach in member_outreach (legacy tracking)
+  const outreach = await insightsDb.recordOutreach({
+    slack_user_id: slackUserId,
+    outreach_type: outreachType,
+    dm_channel_id: channelId,
+    initial_message: message,
+  });
+
+  // Record goal attempt with admin override reason
+  await outboundDb.recordGoalAttempt({
+    slack_user_id: slackUserId,
+    goal_id: goal.id,
+    planner_reason: `Admin override${adminContext ? ' with context' : ''}`,
+    planner_score: 100, // Max priority for admin override
+    decision_method: 'admin_override',
+    outreach_id: outreach.id,
+  });
+
+  // Update user's last_outreach_at
+  await updateLastOutreach(slackUserId);
+
+  // Auto-assign admin as owner if outreach was successful
+  if (triggeredBy) {
+    try {
+      await assignUserStakeholder({
+        slackUserId,
+        workosUserId: user.workos_user_id || undefined,
+        stakeholderId: triggeredBy.id,
+        stakeholderName: triggeredBy.name,
+        stakeholderEmail: triggeredBy.email,
+        role: 'owner',
+        reason: 'outreach',
+      });
+    } catch (error) {
+      logger.warn({ error, slackUserId }, 'Failed to auto-assign user after outreach');
+    }
+  }
+
+  logger.info({
+    outreachId: outreach.id,
+    slackUserId,
+    goalId: goal.id,
+    goalName: goal.name,
+    triggeredBy: triggeredBy?.id,
+    hasAdminContext: !!adminContext,
+    decision_method: 'admin_override',
+  }, 'Sent admin-override outreach');
+
+  return {
+    success: true,
+    outreach_id: outreach.id,
+    dm_channel_id: channelId,
+  };
+}
+
 /**
  * Get current outreach mode
  */
diff --git a/server/src/addie/services/rehearsal-service.ts b/server/src/addie/services/rehearsal-service.ts
index 64e75a5569..5b7dd90c7c 100644
--- a/server/src/addie/services/rehearsal-service.ts
+++ b/server/src/addie/services/rehearsal-service.ts
@@ -333,6 +333,7 @@ export class RehearsalService {
         slack_user_id: `rehearsal_${persona.name?.replace(/\s+/g, '_').toLowerCase() ?? 'user'}`,
         display_name: persona.name,
         is_mapped: isMapped,
+        is_member: true, // Rehearsals assume member context
         engagement_score: persona.engagement_score ?? 50,
         insights: (persona.existing_insights ?? []).map(i => ({
           type: i.type,
diff --git a/server/src/addie/types.ts b/server/src/addie/types.ts
index f1c90516d5..6377e9f009 100644
--- a/server/src/addie/types.ts
+++ b/server/src/addie/types.ts
@@ -169,7 +169,7 @@ export type OutcomeType = 'success' | 'defer' | 'clarify' | 'decline' | 'escalat
 /**
  * Planner decision method
  */
-export type PlannerDecisionMethod = 'rule_match' | 'llm';
+export type PlannerDecisionMethod = 'rule_match' | 'llm' | 'admin_override';
 
 /**
  * Rehearsal session status
@@ -363,6 +363,8 @@ export interface PlannerContext {
     workos_user_id?: string;
     display_name?: string;
     is_mapped: boolean;
+    /** Whether the user's org has an active AgenticAdvertising.org membership */
+    is_member: boolean;
     engagement_score: number;
     insights: Array<{
       type: string;
@@ -375,6 +377,8 @@ export interface PlannerContext {
     type: string;
     size?: string;
     offerings?: string[];
+    /** Whether this is a real company org vs an auto-generated personal workspace */
+    is_personal_workspace?: boolean;
   };
   /** What capabilities has/hasn't this member unlocked? */
   capabilities?: MemberCapabilities;
diff --git a/server/src/db/insights-db.ts b/server/src/db/insights-db.ts
index 2d83836bd5..a35c0022b0 100644
--- a/server/src/db/insights-db.ts
+++ b/server/src/db/insights-db.ts
@@ -347,6 +347,17 @@ export class InsightsDatabase {
     return result.rows[0] || null;
   }
 
+  /**
+   * Get insight type by name
+   */
+  async getInsightTypeByName(name: string): Promise<MemberInsightType | null> {
+    const result = await query<MemberInsightType>(
+      'SELECT * FROM member_insight_types WHERE name = $1',
+      [name]
+    );
+    return result.rows[0] || null;
+  }
+
   /**
    * Update an insight type
    */
diff --git a/server/src/db/migrations/134_cleanup_year_references.sql b/server/src/db/migrations/134_cleanup_year_references.sql
new file mode 100644
index 0000000000..8f6431d067
--- /dev/null
+++ b/server/src/db/migrations/134_cleanup_year_references.sql
@@ -0,0 +1,37 @@
+-- ============================================================================
+-- Migration: 134_cleanup_year_references.sql
+-- Description: Clean up old 2025/2026 references from early migrations
+--
+-- Migration 127 created "Learn 2025/2026 Goals" with insight type "goals_2025"
+-- Migration 129 added "Learn 2026 Plans" with "plans_2026" which is better
+-- Migration 130 added the plans_2026 insight type
+--
+-- This migration:
+-- 1. Disables the old "Learn 2025/2026 Goals" goal (keep for history)
+-- 2. Updates the insight type name from goals_2025 to plans_2025 for clarity
+-- 3. Adds admin_context insight type for admin-provided context
+-- ============================================================================
+
+-- Disable the old goal so it's not selected by planner
+-- We keep it rather than delete because there may be history records
+UPDATE outreach_goals
+SET is_enabled = FALSE
+WHERE name = 'Learn 2025/2026 Goals';
+
+-- Rename the old insight type for clarity (2025 data stays as 2025)
+UPDATE member_insight_types
+SET name = 'plans_2025',
+    description = 'Member plans for agentic advertising in 2025 (historical)'
+WHERE name = 'goals_2025';
+
+-- Add admin_context insight type if not exists
+INSERT INTO member_insight_types (name, description, example_values, is_active, created_by)
+SELECT
+  'admin_context',
+  'Context provided by admin about this member',
+  ARRAY['Focused on publisher sales agent implementation', 'High likelihood of membership', 'Key contact at company'],
+  TRUE,
+  'system'
+WHERE NOT EXISTS (
+  SELECT 1 FROM member_insight_types WHERE name = 'admin_context'
+);
diff --git a/server/src/db/migrations/135_vendor_visibility_goal.sql b/server/src/db/migrations/135_vendor_visibility_goal.sql
new file mode 100644
index 0000000000..5cc9972302
--- /dev/null
+++ b/server/src/db/migrations/135_vendor_visibility_goal.sql
@@ -0,0 +1,81 @@
+-- ============================================================================
+-- Migration: 135_vendor_visibility_goal.sql
+-- Description: Add goal to encourage tech vendors to become members
+--
+-- Vendors (adtech, AI, data companies) benefit from public profiles because
+-- their profiles become visible to other members - great for business dev.
+-- This goal targets engaged non-member vendors to encourage membership.
+-- ============================================================================
+
+-- Add membership_interest insight type if not exists
+INSERT INTO member_insight_types (name, description, example_values, is_active, created_by)
+SELECT
+  'membership_interest',
+  'Interest level in becoming a member',
+  ARRAY['Very interested', 'Needs more info', 'Not right now', 'Price concern', 'Already member through company'],
+  TRUE,
+  'system'
+WHERE NOT EXISTS (
+  SELECT 1 FROM member_insight_types WHERE name = 'membership_interest'
+);
+
+-- Add the vendor membership goal
+INSERT INTO outreach_goals (
+  name, category, description, success_insight_type,
+  requires_mapped, requires_company_type, requires_min_engagement,
+  requires_insights, excludes_insights,
+  base_priority, message_template, follow_up_on_question, is_enabled, created_by
+) VALUES (
+  'Encourage Vendor Membership',
+  'invitation',
+  'Encourage tech vendors to become members for profile visibility and discovery',
+  'membership_interest',
+  TRUE,  -- Must be mapped (have an account)
+  ARRAY['adtech', 'ai', 'data'],  -- Vendor-type companies
+  20,  -- Some engagement shows interest
+  '{}',  -- No required insights
+  '{"membership_interest": "any"}',  -- Skip if we already asked
+  75,
+  E'Hey {{user_name}} - I noticed {{company_name}} has a profile set up with us.\n\nDid you know that by becoming a member, your company profile becomes visible to all other AgenticAdvertising.org members? It''s a great way to get discovered by potential partners and customers in the agentic advertising space.\n\nWould you like to learn more about membership options?',
+  E'Members get their profiles featured in our directory, which is browsed by brands, agencies, and other ad tech companies looking for partners. Plus you get access to working groups, events, and our member-only Slack channels.\n\nWant me to share the membership tiers and pricing?',
+  TRUE,
+  'system'
+);
+
+-- Add outcomes for the vendor membership goal
+INSERT INTO goal_outcomes (goal_id, trigger_type, trigger_value, outcome_type, response_message, insight_to_record, insight_value, priority)
+SELECT
+  g.id,
+  'sentiment',
+  'positive',
+  'success',
+  NULL,  -- Let Addie respond naturally with membership info
+  'membership_interest',
+  'interested',
+  90
+FROM outreach_goals g WHERE g.name = 'Encourage Vendor Membership';
+
+INSERT INTO goal_outcomes (goal_id, trigger_type, trigger_value, outcome_type, response_message, insight_to_record, insight_value, defer_days, priority)
+SELECT
+  g.id,
+  'intent',
+  'question',
+  'clarify',
+  E'Happy to explain more! AgenticAdvertising.org membership gives you:\n\n• Public company profile in our member directory\n• Access to working groups developing agentic ad standards\n• Member-only events and networking\n• Early access to protocol specifications\n\nWe have tiers for different company sizes. Want me to share the options?',
+  NULL,
+  NULL,
+  NULL,
+  80
+FROM outreach_goals g WHERE g.name = 'Encourage Vendor Membership';
+
+INSERT INTO goal_outcomes (goal_id, trigger_type, trigger_value, outcome_type, insight_to_record, insight_value, defer_days, priority)
+SELECT
+  g.id,
+  'sentiment',
+  'negative',
+  'decline',
+  'membership_interest',
+  'not interested',
+  90,  -- Don't ask again for 3 months
+  70
+FROM outreach_goals g WHERE g.name = 'Encourage Vendor Membership';
diff --git a/server/src/routes/admin-insights.ts b/server/src/routes/admin-insights.ts
index 9f86eea615..37dab6a502 100644
--- a/server/src/routes/admin-insights.ts
+++ b/server/src/routes/admin-insights.ts
@@ -17,6 +17,7 @@ import { getPool } from '../db/client.js';
 import {
   runOutreachScheduler,
   manualOutreach,
+  manualOutreachWithGoal,
   getOutreachMode,
   canContactUser,
 } from '../addie/services/proactive-outreach.js';
@@ -753,6 +754,54 @@ export function createAdminInsightsRouter(): { pageRouter: Router; apiRouter: Ro
     }
   });
 
+  // POST /api/admin/outreach/send-with-goal - Send outreach with a specific goal (admin override)
+  apiRouter.post('/outreach/send-with-goal', requireAuth, requireAdmin, async (req, res) => {
+    try {
+      const { slack_user_id, goal_id, admin_context } = req.body;
+
+      // Validate inputs
+      const goalIdNum = parseInt(goal_id, 10);
+      if (!slack_user_id || isNaN(goalIdNum) || goalIdNum <= 0) {
+        return res.status(400).json({ error: 'Valid slack_user_id and goal_id are required' });
+      }
+
+      // Check if user can be contacted
+      const eligibility = await canContactUser(slack_user_id);
+      if (!eligibility.canContact) {
+        return res.status(400).json({ error: eligibility.reason });
+      }
+
+      // Pass admin info for auto-assignment
+      const triggeredBy = req.user ? {
+        id: req.user.id,
+        name: `${req.user.firstName || ''} ${req.user.lastName || ''}`.trim() || req.user.email,
+        email: req.user.email,
+      } : undefined;
+
+      const result = await manualOutreachWithGoal(
+        slack_user_id,
+        goalIdNum,
+        admin_context,
+        triggeredBy
+      );
+
+      if (result.success) {
+        logger.info({
+          slackUserId: slack_user_id,
+          goalId: goal_id,
+          hasContext: !!admin_context,
+          triggeredBy: req.user?.id,
+        }, 'Admin-override outreach sent');
+        res.json(result);
+      } else {
+        res.status(400).json({ error: result.error });
+      }
+    } catch (error) {
+      logger.error({ err: error }, 'Error sending admin-override outreach');
+      res.status(500).json({ error: 'Internal server error' });
+    }
+  });
+
   // GET /api/admin/outreach/check/:slackUserId - Check if user can be contacted
   apiRouter.get('/outreach/check/:slackUserId', requireAuth, requireAdmin, async (req, res) => {
     try {
diff --git a/server/src/routes/admin-outbound.ts b/server/src/routes/admin-outbound.ts
index d38e2d75ee..8df3d1aaf9 100644
--- a/server/src/routes/admin-outbound.ts
+++ b/server/src/routes/admin-outbound.ts
@@ -444,6 +444,7 @@ export function createAdminOutboundRouter(): { pageRouter: Router; apiRouter: Ro
           workos_user_id: memberContext?.workos_user?.workos_user_id,
           display_name: memberContext?.slack_user?.display_name ?? undefined,
           is_mapped: !!memberContext?.is_mapped,
+          is_member: memberContext?.is_member ?? false,
           engagement_score: 0, // Could compute from activity later
           insights: insights.map(i => ({
             type: i.insight_type_name ?? 'unknown',
@@ -451,10 +452,17 @@ export function createAdminOutboundRouter(): { pageRouter: Router; apiRouter: Ro
             confidence: i.confidence,
           })),
         },
-        company: memberContext?.organization ? {
-          name: memberContext.organization.name,
-          type: 'unknown', // Would need to look up company_type from organization
-        } : undefined,
+        company: memberContext?.organization ? (() => {
+          const orgName = memberContext.organization!.name;
+          // Check for both straight and curly apostrophes in personal workspace names
+          const isPersonalWorkspace = orgName.toLowerCase().endsWith("'s workspace") ||
+                                      orgName.toLowerCase().endsWith("'s workspace");
+          return {
+            name: isPersonalWorkspace ? 'your account' : orgName,
+            type: 'unknown', // Would need to look up company_type from organization
+            is_personal_workspace: isPersonalWorkspace,
+          };
+        })() : undefined,
         history,
         contact_eligibility: {
           can_contact: contactEligibility.canContact,
@@ -531,6 +539,7 @@ export function createAdminOutboundRouter(): { pageRouter: Router; apiRouter: Ro
           workos_user_id: workosUserId,
           display_name: memberContext?.slack_user?.display_name ?? undefined,
           is_mapped: !!memberContext?.is_mapped,
+          is_member: memberContext?.is_member ?? false,
           engagement_score: capabilities.slack_message_count_30d > 10 ? 75 :
                             capabilities.slack_message_count_30d > 5 ? 50 :
                             capabilities.slack_message_count_30d > 0 ? 25 : 0,
@@ -540,10 +549,17 @@ export function createAdminOutboundRouter(): { pageRouter: Router; apiRouter: Ro
             confidence: i.confidence,
           })),
         },
-        company: memberContext?.organization ? {
-          name: memberContext.organization.name,
-          type: 'unknown',
-        } : undefined,
+        company: memberContext?.organization ? (() => {
+          const orgName = memberContext.organization!.name;
+          // Check for both straight and curly apostrophes in personal workspace names
+          const isPersonalWorkspace = orgName.toLowerCase().endsWith("'s workspace") ||
+                                      orgName.toLowerCase().endsWith("'s workspace");
+          return {
+            name: isPersonalWorkspace ? 'your account' : orgName,
+            type: 'unknown',
+            is_personal_workspace: isPersonalWorkspace,
+          };
+        })() : undefined,
         capabilities,
         history,
         contact_eligibility: {
diff --git a/server/src/routes/admin.ts b/server/src/routes/admin.ts
index a0052ce663..9ad1d01efd 100644
--- a/server/src/routes/admin.ts
+++ b/server/src/routes/admin.ts
@@ -260,12 +260,18 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
                 canContactUser(slackUserId),
               ]);
 
+              // Check if this is a personal workspace (auto-generated "User's Workspace" name)
+              const orgName = context.organization?.name ?? '';
+              const isPersonalWorkspace = orgName.toLowerCase().endsWith("'s workspace") ||
+                                          orgName.toLowerCase().endsWith("'s workspace");
+
               const plannerCtx: PlannerContext = {
                 user: {
                   slack_user_id: slackUserId,
                   workos_user_id: workosUserId,
                   display_name: context.slack_user?.display_name ?? undefined,
                   is_mapped: !!workosUserId,
+                  is_member: context.is_member ?? false,
                   engagement_score: capabilities.slack_message_count_30d > 10 ? 75 :
                                     capabilities.slack_message_count_30d > 5 ? 50 :
                                     capabilities.slack_message_count_30d > 0 ? 25 : 0,
@@ -276,8 +282,9 @@ export function createAdminRouter(): { pageRouter: Router; apiRouter: Router } {
                   })),
                 },
                 company: context.organization ? {
-                  name: context.organization.name,
+                  name: isPersonalWorkspace ? 'your account' : context.organization.name,
                   type: 'unknown',
+                  is_personal_workspace: isPersonalWorkspace,
                 } : undefined,
                 capabilities,
                 history,