People & HR Use Cases

Bulk Employment
Letter Generation

Bulk Employment Letter Generation

Generate and deliver hundreds of bespoke employment letters in minutes

The Challenges

Usually when organizations grow, and are restructured, the HR team receives little notice before they are expected to send out hundreds of personalized letters to employees. These business-critical documents are often manually administered through spreadsheets and mail-merges, requiring significant manual data entry. Given the tight deadlines, this leaves enormous room for human error, increasing the chances of incorrect or non-compliant letters. Most of the time, these manual processes cannot handle complex cases with conditional clauses and approval collection, requiring employees to manually engage with HR through ad-hoc emails.

How Checkbox Solves Bulk Employment Letter Generation

Challenges How does Checkbox address it?

High turn-around time for letters which negatively impacts the experience of employees.

Bulk-generate hundreds of bespoke letters in minutes by uploading a single CSV. The generated bespoke documents can feature:
1. Conditional clauses – only the relevant clauses are inserted into the document and numbered automatically.
2. Dynamic tables to structure information in rows and columns that are adjusted automatically to the content.

High risk of human error from manually creating letters, and non-compliance if the incorrect letter is sent.

The generation of documents is automated by populating an underlying master template which is compliant by design. 

Manual look up and rekeying of data from multiple sources, such as CRM systems. 

Data required for the documents is automatically retrieved from various systems including Hubspot, Salesforce, and SharePoint through REST API. 

Requesting for approval, and following-up with employees is time-consuming and low-value.

Automatically escalate relevant cases and streamline the approval process with automated workflow.

Horizontal view of the approval and contract status is lost through back-and-forth emails.  

Track the real-time status with Checkbox dashboards where information such as letter status, e-signature status, and approval timestamps can be displayed.

Minimal visibility on the finalized document post-signature. 

Generated and signed documents are all stored in Checkbox and can be sent to store in other document repository systems such as Google Drive, SharePoint, iManage, or NetDocuments.

Dashboard Analytics further allows HR teams to derive key business insights, fuelling process improvement and organisational efficiency gains.

Key Features


  • Rapid bulk generation of letters and agreements

    Bulk-generate letters with just a few clicks to empower HR teams to maintain speed and accuracy through busy periods.

  • Dynamic letter and agreement generation and approval

    Generate bespoke letters and agreements that are error-free and compliant every time, making approval easy and minimizing inefficient back-and-forth in the process.

  • Intuitive digital signing

    Makes the document-signing process paper-less and painless, with native e-signature tools and in-built reminders allowing for quick and easy signing by all parties.

  • Comprehensive audit trails and process management tools

    Monitor and manage all letters and agreements at-a-glance through Checkbox dashboards and audit trails. Gain valuable process insight through assessment time-tracking and response analytics to support organizational efficiency at scale.

  • Improve maintainability

    Through no-code, the solution can be easily and independently modified for any contract content, logic or format changes.


How Does Checkbox Automate This?

1. Bulk upload employee information

The no-code platform can pull information from enterprise systems, including CSV files, Salesforce, and other ERP systems, in a HR-led process that automatically creates bespoke letters.

2. Generate a draft letter or agreement for HR/Hiring manager review

Any approvals required from HR supervisors or hiring managers can be seamlessly captured using Checkbox’s human-in-the loop workflow functionality. Approvers can be sent a draft letter, which they can approve, edit or send back for further information.

3. Automatically determine the necessary approval path for your document

Checkbox’s complex calculation engine will automatically assign the document to the appropriate business stakeholders for review, and approval, with automated reminders.

4. Monitor the status of all agreements and letters at-a-glance

Process administrators can use Checkbox Dashboards to manage and monitor the progress and audit trails of all letters and agreements. Dashboards also allow for bespoke analytics on data captured and time taken to support organizational efficiency initiatives.

Get started with your digital transformation journey

See how Checkbox fits in with your organization by contacting us and requesting a free demo