How and Why HR Teams Should Be Automating Employment Letters

September 1, 2022
August 14, 2023

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Talented and driven people are at the heart of every company’s success, which is why hiring new people should be one of the most exciting projects for the HR department.

However, through our extensive work with HR teams, we’ve found that, often the lengthy and extremely manual hiring process leave HR teams drowning in work; work that is seen as less than exciting and very manual. In fact, a recent Forrester report stated that 50% of the HR department’s time is spent just processing employee information and responding to inquiries. On top of this, they are expected to manage contract generation, pay roles, employee relations and cross-company training. With HR teams struggling to even manage existing workloads, it’s no wonder that new employee recruitment and onboarding processes take up to months. This is not only detrimental for meeting recruitment quotas and hiring the best talent quickly but also leaves a negative impression on candidates.

With several process driven problems on the horizon, this is exactly why leading HR teams are looking to automate standard and low risk employment letters such that they can free up their time to focus on what really matters, the people.

“At CCA, the people and cultures team have automated performance review, workflows, bulk generation of individualised employee letters and have leveraged Checkbox to upskill employees in software-building and IT project management. This has allowed the team to focus on the people rather than the processes, whilst being able to react quickly to issues and roll out solutions organisation- wide at a velocity that was unachievable previously.”

The Current Process

Employee letters and agreements are business-critical documents that are often manually administered by the HR team. While it is common for this process to be managed using spreadsheets and mail-merges, this method still requires HR teams to engage in significant manual data entry which leaves room for human error and takes their focus away from the people and into the process. Subsequently, the employee experience is impacted too, requiring employees to engage with HR through manual workflows in collecting information and signing documents.

Critial Pain Points

  • High turn-around time for documents which can slow down business deals.
  • High risk of human error from manually creating contracts, and non-compliance if the incorrect, or an outdated template is used.  
  • Manual look up and rekeying of data from multiple sources, such as CRM systems.
  • Clients experience a tedious and lengthy contract signing process by having to download, sign and re-send their contract.
  • Horizontal view of the approval and contract status is lost through back-and-forth emails.  
  • Minimal visibility on the finalised document post-signature.


The Checkbox automation platform empowers People and HR teams to build automated employee letter generation tools using drag and drop. Trusted by the best brands across HR teams of all sizes, Checkbox enables HR teams to generate and send letters to employees that are personalised to each recipient, including dynamic clauses and recipient-specific calculations. Access our existing Employee Letter Generation app template to build your team’s automation solution within just a few hours.


  • Seamless information capture
    Complete employee information intake in minutes with an intuitive form-based digital interface.  
  • Dynamic letter and agreement generation and approval
    Generate bespoke letters and agreements that are error-free and compliant every time, making approval easy and minimising inefficient back-and-forth in the process.  
  • 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.  
  • 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 organisational efficiency at scale.
  • Improve maintainability  
    Through no-code, the solution can be easily and independently modified for any contract content, logic or format changes.

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