TL;DR

• Simplify helps you create and manage different cover letter versions for different applications.

• You can start from a template, upload an existing letter, or generate one using Simplify+.

• Each cover letter stays editable and saved separately, so you can tailor without overwriting previous versions.

About Cover Letters

Cover letters work best when they are written for a specific role and company.

Different applications often require different emphasis, tone, or examples depending on the role. Simplify's cover letter workflow is designed around that reality. Instead of rewriting from scratch every time, you can build from an existing version, tailor it for a specific application, and keep each version organized inside Documents.

Starting from an existing letter or template

There are a few common ways people begin a cover letter on Simplify:

• starting from one of Simplify's templates

• uploading an existing cover letter

• creating a new one from scratch

• generating one with AI using Simplify+

The templates are meant to give you a usable starting structure for different industries and writing styles. Uploaded cover letters become editable versions inside Simplify, so you can continue tailoring them instead of managing separate files outside the platform.

No matter how the letter starts, it becomes part of your Documents workspace alongside your resumes and other application materials.

For more on using Simplify’s Cover Letter templates: Using Cover Letter Templates

Tailoring a cover letter for a specific role

The cover letter editor is designed for iteration and reuse.

Most users are not writing an entirely new letter for every application. Instead, they usually keep a strong base version and adjust:

• the company and role context

• the opening paragraph

• the experiences being emphasized

• the tone or wording for a specific industry

• the connection between their background and the job description

This makes it easier to maintain consistency across applications while still tailoring each letter toward the role.

Your edits save automatically, and each tailored letter can live as its own version inside Documents. That matters once you start applying across multiple companies or role types and need to keep track of what you used where.

AI cover letter tailoring (Simplify+)

Simplify+ adds AI-assisted cover letter generation and tailoring.

You can generate a new cover letter using:

• your Simplify profile

• your resume

• the target job description

You can also take an existing cover letter or template and have AI tailor it toward a specific role instead of starting over manually.

The AI-generated version stays fully editable. Most users treat it as a strong first draft, then adjust wording, tone, or examples before exporting the final version.

For more on AI-assisted tailoring, see What's included in Simplify+.

Simplify+ also brings cover letter generation into Simplify Copilot during applications, so you can tailor application materials without leaving the application flow.

Managing multiple cover letter versions

Each cover letter is stored as its own document inside the Cover Letters section.

Over time, many users build several versions for:

• different industries

• different role types

• different writing styles

• company-specific applications

Keeping those versions separated matters because cover letter tailoring is usually cumulative. Older letters often become useful starting points for future applications with similar requirements.

The search bar inside Documents also makes it easier to return to older versions once your application history grows.