Add textual signature to generated PDFs

backend/app/controllers/internal/companies/documents_controller.rb

@@ -11,6 +11,14 @@ def create
     head :created
   end
 
+  def signed
+    document = Current.company.documents.find(params[:id])
+    authorize document
+
+    CreateDocumentPdfJob.perform_sync(document.id, document.text)
+    head :no_content
+  end
+
   private
     def document_params
       params.require(:document).permit(:name, :document_type, :text)

backend/app/models/company.rb

@@ -46,7 +46,7 @@ class Company < ApplicationRecord
   has_many :administrators, through: :company_administrators, source: :user
   has_many :company_lawyers
   has_many :lawyers, through: :company_lawyers, source: :user
-  has_one :primary_admin, -> { order(id: :asc) }, class_name: "CompanyAdministrator"
+  belongs_to :primary_admin, class_name: "CompanyAdministrator", optional: true
   has_many :company_workers
   has_many :company_investor_entities
   has_many :contracts
@@ -120,6 +120,8 @@ def deactivate! = update!(deactivated_at: Time.current)
 
   def active? = deactivated_at.nil?
 
+  def primary_admin = super || company_administrators.order(:id).first
+
   def logo_url
     return logo.url if logo.attached?
 

backend/app/policies/document_policy.rb

@@ -4,4 +4,8 @@ class DocumentPolicy < ApplicationPolicy
   def create?
     company_administrator?
   end
+
+  def signed?
+    company_administrator? || record.signatures.any? { |signature| signature.user == user }
+  end
 end

backend/app/sidekiq/create_document_pdf_job.rb

@@ -6,7 +6,11 @@ class CreateDocumentPdfJob
 
   def perform(document_id, document_text)
     document = Document.find(document_id)
-    pdf = CreatePdf.new(body_html: ActionController::Base.helpers.sanitize(document_text)).perform
+    body_html = ApplicationController.render template: "templates/signed_document",
+                                             locals: { body_html: ActionController::Base.helpers.sanitize(document_text), document: },
+                                             layout: false,
+                                             formats: [:html]
+    pdf = CreatePdf.new(body_html:).perform
     document.attachments.attach(
       io: StringIO.new(pdf),
       filename: "#{document.name}.pdf",

backend/app/views/templates/signed_document.erb

@@ -0,0 +1,111 @@
+<style>
+  body {
+      font-family: "ABC Whyte", sans-serif;
+  }
+
+  .column {
+    display: grid;
+    gap: 1rem;
+  }
+
+  .item {
+    display: grid;
+    gap: 0.5rem;
+    border-bottom: 1px solid #1D1E172E;
+  }
+
+  .label {
+    text-transform: uppercase;
+    color: #1D1E17A1;
+    font-weight: 500;
+    font-size: 0.75rem;
+  }
+
+  .signature {
+    font-size: 1.25rem;
+    font-style: italic;
+    border: solid 1px #1D1E172E;
+    padding: 1rem;
+    font-family: "Caveat", cursive;
+    text-align: center;
+  }
+</style>
+
+<%= body_html %>
+<br /><br /><br />
+<b>IN WITNESS WHEREOF</b>, the parties have executed this Agreement as of the Effective Date.
+<%
+  company_representative = document.company.primary_admin.user
+  signature = document.signatures.first
+  signatory = signature&.user
+%>
+<div style="display: grid; grid-template-columns: 1fr 1fr; margin-top: 1.25rem; gap: 2rem">
+  <div class="column">
+    <b>CLIENT</b>
+    <div class="item" style="border-bottom: none;">
+      <div class="label">Signature</div>
+      <div class="signature">
+        <%= company_representative.legal_name %>
+      </div>
+    </div>
+    <div class="item">
+      <div class="label">Name</div>
+      <%= company_representative.legal_name %>
+    </div>
+    <div class="item">
+      <div class="label">Title</div>
+      Chief Executive Officer
+    </div>
+    <div class="item">
+      <div class="label">Country</div>
+      <%= company_representative.display_country %>
+    </div>
+    <div class="item">
+      <div class="label">Address</div>
+      <%= "#{company_representative.street_address}, #{company_representative.city}, #{company_representative.state}" %>
+    </div>
+    <div class="item">
+      <div class="label">Email</div>
+      <%= company_representative.display_email %>
+    </div>
+    <div class="item">
+      <div class="label">Date signed</div>
+      <%= company_representative.created_at.strftime("%B %d, %Y") %>
+    </div>
+  </div>
+  <div class="column">
+    <b>CONTRACTOR</b>
+    <div class="item" style="border-bottom: none;">
+      <div class="label">Signature</div>
+      <div class="signature">
+        <%= signatory&.legal_name %>
+      </div>
+    </div>
+    <div class="item">
+      <div class="label">Name</div>
+      <%= signatory&.legal_name %>
+    </div>
+    <div class="item">
+      <div class="label">Legal Entity</div>
+      <%= signatory&.billing_entity_name %>
+    </div>
+    <div class="item">
+      <div class="label">Country</div>
+      <%= signatory&.display_country %>
+    </div>
+    <div class="item">
+      <div class="label">Address</div>
+      <% if signatory.present? %>
+        <%= "#{signatory.street_address}, #{signatory.city}, #{signatory.state}" %>
+      <% end %>
+    </div>
+    <div class="item">
+      <div class="label">Email</div>
+      <%= signatory&.display_email %>
+    </div>
+    <div class="item">
+      <div class="label">Date signed</div>
+      <%= signature&.signed_at&.strftime("%B %d, %Y") %>
+    </div>
+  </div>
+</div>

backend/config/routes/internal.rb

@@ -82,7 +82,11 @@
     resources :dividend_computations, only: [:index, :create, :show]
     resources :dividend_rounds, only: [:create]
     resources :templates, only: [:index, :show, :update]
-    resources :documents, only: [:create]
+    resources :documents, only: [:create] do
+      member do
+        post :signed
+      end
+    end
     resources :share_classes, only: [:index]
     resources :cap_tables, only: [] do
       collection do

backend/db/migrate/20251225151433_add_primary_admin_id_to_companies.rb

@@ -0,0 +1,5 @@
+class AddPrimaryAdminIdToCompanies < ActiveRecord::Migration[8.0]
+  def change
+    add_reference :companies, :primary_admin, null: true, index: true
+  end
+end

backend/db/schema.rb

@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[8.0].define(version: 2025_10_02_213957) do
+ActiveRecord::Schema[8.0].define(version: 2025_12_25_151433) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "pg_catalog.plpgsql"
 
@@ -105,8 +105,10 @@
     t.jsonb "json_data", default: {"flags" => []}, null: false
     t.boolean "equity_enabled", default: false, null: false
     t.string "invite_link"
+    t.bigint "primary_admin_id"
     t.index ["external_id"], name: "index_companies_on_external_id", unique: true
     t.index ["invite_link"], name: "index_companies_on_invite_link", unique: true
+    t.index ["primary_admin_id"], name: "index_companies_on_primary_admin_id"
   end
 
   create_table "company_administrators", force: :cascade do |t|

backend/spec/factories/document_signatures.rb

@@ -0,0 +1,13 @@
+# frozen_string_literal: true
+
+FactoryBot.define do
+  factory :document_signature do
+    document
+    user
+    title { "Signer" }
+
+    trait :signed do
+      signed_at { Time.current }
+    end
+  end
+end

backend/spec/models/company_spec.rb

@@ -5,7 +5,7 @@
 
   describe "associations" do
     it { is_expected.to have_many(:company_administrators) }
-    it { is_expected.to have_one(:primary_admin).class_name("CompanyAdministrator") }
+    it { is_expected.to belong_to(:primary_admin).class_name("CompanyAdministrator").optional(true) }
     it { is_expected.to have_many(:administrators).through(:company_administrators).source(:user) }
     it { is_expected.to have_many(:company_lawyers) }
     it { is_expected.to have_many(:lawyers).through(:company_lawyers).source(:user) }
@@ -470,6 +470,18 @@
     end
   end
 
+  describe "#primary_admin" do
+    it "returns the primary admin" do
+      company = create(:company)
+      admin = create(:company_administrator, company:)
+      expect(company.primary_admin).to eq admin
+      admin2 = create(:company_administrator, company:)
+      expect(company.primary_admin).to eq admin
+      company.update!(primary_admin: admin2)
+      expect(company.primary_admin).to eq admin2
+    end
+  end
+
   describe "#active?" do
     it "returns true if deactivated_at is not set, false otherwise" do
       company = build(:company)

backend/spec/sidekiq/create_document_pdf_job_spec.rb

@@ -4,6 +4,7 @@
   include ActiveJob::TestHelper
 
   let(:company) { create(:company) }
+  let!(:admin) { create(:company_administrator, company:) }
   let(:pdf_service) { instance_double(CreatePdf, perform: "pdf content") }
 
   before do
@@ -19,13 +20,34 @@
 
     sanitized_text = ActionController::Base.helpers.sanitize(document.text)
     expect(sanitized_text).to eq("<h1>Test</h1>alert('x')<img src=\"x\">")
-    expect(CreatePdf).to receive(:new).with(body_html: sanitized_text).and_return(pdf_service)
+    expect(CreatePdf).to receive(:new) do |args|
+      expect(args[:body_html]).to include(sanitized_text)
+      expect(args[:body_html]).to include(admin.user.legal_name)
+    end.and_return(pdf_service)
 
     expect { described_class.new.perform(document.id, document.text) }
       .to change { document.reload.attachments.attached? }.from(false).to(true)
 
     attachment = document.reload.attachments.first
     expect(attachment.filename.to_s).to eq("#{document.name}.pdf")
     expect(attachment.content_type).to eq("application/pdf")
+
+    user = create(:user)
+    signature = create(:document_signature, document:, user:, title: "Signer")
+    expect(CreatePdf).to receive(:new) do |args|
+      expect(args[:body_html]).to include(sanitized_text)
+      expect(args[:body_html]).to include(admin.user.legal_name)
+      expect(args[:body_html]).to include(user.legal_name)
+    end.and_return(pdf_service)
+    described_class.new.perform(document.id, document.text)
+
+    signature.update!(signed_at: Date.new(2025, 12, 20))
+    expect(CreatePdf).to receive(:new) do |args|
+      expect(args[:body_html]).to include(sanitized_text)
+      expect(args[:body_html]).to include(admin.user.legal_name)
+      expect(args[:body_html]).to include(user.legal_name)
+      expect(args[:body_html]).to include("December 20, 2025")
+    end.and_return(pdf_service)
+    described_class.new.perform(document.id, document.text)
   end
 end

e2e/tests/company/documents/documents.spec.ts

@@ -89,7 +89,7 @@ test.describe("Documents", () => {
     const { company, adminUser } = await companiesFactory.createCompletedOnboarding();
     await documentsFactory.create({ companyId: company.id, text: "Test document text" });
     const { user: recipient } = await usersFactory.create({ legalName: "Recipient 1" });
-    await companyContractorsFactory.create({ companyId: company.id, userId: recipient.id });
+    await companyContractorsFactory.create({ companyId: company.id, userId: recipient.id }, { withoutContract: true });
     await login(page, adminUser, "/documents");
     await logout(page);
     await expect(page.getByRole("heading", { name: "Documents" })).toBeVisible();
@@ -110,6 +110,16 @@ test.describe("Documents", () => {
     await expect(page.getByText("Some other text")).toBeVisible();
     await page.getByRole("button", { name: "Add your signature" }).click();
     await page.getByRole("button", { name: "Agree & Submit" }).click();
+
+    await expect(page.getByText("No results.")).toBeVisible();
+    await page.locator("main").getByRole("button", { name: "Filter" }).click();
+    await page.getByRole("menuitem", { name: "Status" }).click();
+    await page.getByRole("menuitemcheckbox", { name: "All" }).click();
+    await expect(page.getByRole("menuitem")).toHaveCount(0);
+    await expect(page.locator("tbody tr")).toHaveCount(1);
+    await expect(page.getByText("Signed")).toBeVisible();
+    await page.getByRole("button", { name: "Open menu" }).click();
+    await expect(page.getByRole("menuitem", { name: "Download" })).toBeVisible();
   });
 
   test("shows the correct names for documents", async ({ page }) => {

frontend/db/schema.ts

@@ -1638,6 +1638,7 @@ export const companies = pgTable(
     conversionSharePriceUsd: numeric("conversion_share_price_usd"),
     jsonData: jsonb("json_data").notNull().$type<{ flags: string[] }>().default({ flags: [] }),
     inviteLink: varchar("invite_link"),
+    primaryAdminId: bigint("primary_admin_id", { mode: "bigint" }),
   },
   (table) => [
     index("index_companies_on_external_id").using("btree", table.externalId.asc().nullsLast().op("text_ops")),

frontend/trpc/routes/documents.ts

@@ -15,6 +15,7 @@ import {
 import { companyProcedure, createRouter } from "@/trpc";
 import { simpleUser } from "@/trpc/routes/users";
 import { assertDefined } from "@/utils/assert";
+import { signed_company_document_url } from "@/utils/routes";
 
 const visibleDocuments = (companyId: bigint, userId: bigint | SQLWrapper | undefined) =>
   and(
@@ -57,7 +58,7 @@ export const documentsRouter = createRouter({
         )
         .leftJoin(activeStorageBlobs, eq(activeStorageAttachments.blobId, activeStorageBlobs.id))
         .where(where)
-        .orderBy(desc(documents.id));
+        .orderBy(desc(documents.id), desc(activeStorageAttachments.id));
 
       const signatories = await db.query.documentSignatures.findMany({
         columns: { documentId: true, title: true, signedAt: true },
@@ -114,7 +115,7 @@ export const documentsRouter = createRouter({
       .limit(1);
     if (!document) throw new TRPCError({ code: "NOT_FOUND" });
 
-    return await db.transaction(async (tx) => {
+    const result = await db.transaction(async (tx) => {
       await tx
         .update(documentSignatures)
         .set({ signedAt: new Date() })
@@ -142,5 +143,16 @@ export const documentsRouter = createRouter({
 
       return { documentId: input.id, complete: allSigned };
     });
+
+    // Generate PDF outside the transaction so signedAt is committed
+    if (result.complete) {
+      const response = await fetch(signed_company_document_url(ctx.company.externalId, document.documents.id), {
+        method: "POST",
+        headers: ctx.headers,
+      });
+      if (!response.ok) throw new TRPCError({ code: "INTERNAL_SERVER_ERROR", message: await response.text() });
+    }
+
+    return result;
   }),
 });