diff --git a/ee/app/models/license.rb b/ee/app/models/license.rb
index ebb3af11940086648984857138843fbbe644f7ae..bcba572ab94bc348a95d35012e3e13ee64c32e1c 100644
--- a/ee/app/models/license.rb
+++ b/ee/app/models/license.rb
@@ -47,6 +47,7 @@ class License < ApplicationRecord
   after_create :update_trial_setting
   after_commit :reset_current
   after_commit :reset_future_dated, on: [:create, :destroy]
+  after_commit :update_billable_user_counts, on: :create
 
   scope :cloud, -> { where(cloud: true) }
   scope :recent, -> { reorder(id: :desc) }
@@ -361,6 +362,11 @@ def update_trial_setting
     settings.update license_trial_ends_on: license.expires_at
   end
 
+  def update_billable_user_counts
+    identifier = Analytics::UsageTrends::Measurement.identifiers[:billable_users]
+    ::Analytics::UsageTrends::CounterJobWorker.perform_async(identifier, User.minimum(:id), User.maximum(:id), Time.zone.now)
+  end
+
   def paid?
     [License::STARTER_PLAN, License::PREMIUM_PLAN, License::ULTIMATE_PLAN].include?(plan)
   end
diff --git a/ee/spec/models/license_spec.rb b/ee/spec/models/license_spec.rb
index f395a55b5a48a144c9ce066493c411cea9e2cb9c..ac92cee41eb082c7c36c4ada93fcdd25018e6412 100644
--- a/ee/spec/models/license_spec.rb
+++ b/ee/spec/models/license_spec.rb
@@ -18,6 +18,10 @@ def build_license_with_add_ons(add_ons, plan: nil)
     build(:license, data: gl_license.export)
   end
 
+  before do
+    allow(::Analytics::UsageTrends::CounterJobWorker).to receive(:perform_async)
+  end
+
   describe 'validations' do
     describe '#valid_license' do
       subject(:license) { build(:license, data: gl_license.class.encryptor.encrypt(gl_license.to_json)) }
@@ -626,6 +630,14 @@ def current_license_cached_value
         end
       end
     end
+
+    describe '#update_billable_user_counts' do
+      subject!(:license) { create(:license, data: gl_license.export, starts_at: Date.current) }
+
+      it 'updates billable user counts' do
+        expect(::Analytics::UsageTrends::CounterJobWorker).to have_received(:perform_async).once
+      end
+    end
   end
 
   describe 'Scopes' do
diff --git a/ee/spec/requests/api/license_spec.rb b/ee/spec/requests/api/license_spec.rb
index f8c12a0004c8c9e761503aabe50586f775e78f4c..3dcec170b170c57cf9c801af589382ccc669afdd 100644
--- a/ee/spec/requests/api/license_spec.rb
+++ b/ee/spec/requests/api/license_spec.rb
@@ -235,7 +235,7 @@ def license_json(license)
   end
 
   describe 'PUT /license/:id/refresh_billable_users' do
-    let(:license) { create(:license) }
+    let!(:license) { create(:license) }
     let(:endpoint) { "/license/#{license.id}/refresh_billable_users" }
 
     before do