Tailorly 2.3 documentation

Everything Tailorly can do

Tailorly is one chat-driven workspace for your whole job search. Ask in plain English and it routes the work to the right place — advice, live resume edits, job discovery, fit scoring, auto-apply, and a public profile. This guide walks through every feature from a user's point of view, step by step, with playable demos of the real interface.

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How Tailorly works

There is no menu of tools to learn. You type what you want in the chat, and Tailorly decides what you are really asking for — coaching, an edit, a job search, a tailored resume, a cover letter, or an application — and opens the right panel beside the conversation.

Everything stays grounded in your resume. The same profile that powers advice also powers tailoring, match scoring, and your public profile, so you never re-paste your background between tools.

You type a messageTailorly classifies intentIt opens the right panelYou reviewYou accept / save

Grounded advice

Recruiter-style coaching that reads your real resume — never invents jobs or numbers.

Live resume editing

Rewrite a line, a section, several sections, or the whole resume in a live preview.

Tailoring & ATS

Align a resume to a specific posting and see an ATS-style score with keyword gaps.

Job search & matching

Find real roles and see a Tailorly match score on every card.

Fit scoring

A deep, category-by-category breakdown of whether a role is worth your time.

Auto-apply agent

A browser agent fills and submits applications while you watch and approve.

Tailorly profile

Turn your resume into a polished public profile or portfolio site.

Cover letters & exports

Draft letters and export ATS-safe PDF / DOCX when you are ready to send.

One connected context

Your resume, jobs, and profile share one source of truth across every feature.

Always review before you send

AI can make mistakes. Treat scores, rewrites, and suggestions as guidance — read every change in the preview and verify facts before you use anything in a real application.

Coaching

Grounded career & resume advice

When your message reads like a question, Tailorly answers like a blunt, recruiter-minded coach. It receives your full resume (profile, summary, experience, projects, skills, education, certificates) as read-only context and never changes anything — advice and edits are separate on purpose.

Your wording is mapped to one of six advice modes, each with a fixed answer shape so responses stay consistent and easy to skim.

Resume review

Verdict, strengths, weaknesses, section-by-section notes, top fixes, and an “apply now vs improve first” call.

ATS-style analysis

A score out of 100, parsing vs keyword breakdown, why it isn’t higher, and a realistic “after fixes” range.

Resume improvement

Biggest improvement buckets, before/after rewrites (no fake metrics), in priority order.

Career coach

Where you stand, roles to target by fit level, gaps, and a two-week / 30-day plan.

Job match

A match score and tailoring order when you paste a specific job description.

General Q&A

A direct answer first, a short explanation, then practical steps and a clear takeaway.

What the answer looks like

  • Clear headings so you can jump straight to the verdict, gaps, or next steps.
  • Numbered steps with the point on the same line as the number, sub-points beneath.
  • Important skills, tools, roles, metrics, and section names emphasized so you can skim.
  • No invented jobs or numbers — if data is missing, the answer says so out loud.

Step by step

  1. Ask a question in chat

    Type something like a review request or a fit question. No command needed.

  2. Tailorly picks an advice mode

    Your phrasing maps to review, ATS, improvement, coach, job match, or general Q&A.

  3. The answer streams in

    You watch a structured, scannable response build word by word, grounded in your resume.

  4. Decide your next move

    If you agree with the plan, send a separate message asking Tailorly to make the edits.

Try these prompts

›

Give me a blunt resume review for a senior backend role: verdict, top weaknesses, and whether I should apply as-is.

›

Estimate my ATS score and list the top ten honest improvements — do not inflate the number.

›

Based on my resume, what roles am I realistically positioned for in the next 90 days — strong, moderate, and stretch?

›

How do I explain a six-month employment gap without sounding defensive on the resume?

Editing

Live resume editing

Describe a change in normal sentences and Tailorly figures out the scope — a single bullet, one role or project, a whole section, several sections at once, or the entire resume. Every change lands in a live preview first; nothing is saved until you say so.

Describe the changeWatch the preview updateReview the diffAcceptSave

Whole section vs one entry

“Improve my experience section” targets the entire block. Name a company, product, or title — or use ordinals like “first job” — to narrow to one entry. Sometimes the UI asks you to pick which one.

Bullets, titles & small fields

Ask for a specific shape: number of bullets per role, shorter lines, stronger metrics where you already have numbers, or fixing a title or dates.

Several sections in one message

One request can update two or more parts — say, summary and experience, or skills plus a new project. Tailorly runs them in sequence and shows a combined result.

Truth controls

Tell Tailorly what must stay fixed — “don’t invent metrics”, “keep employers and dates unchanged” — and it respects those constraints while rewriting.

Step by step

  1. Type your edit

    For example, “Make my summary more confident and leadership-focused.” Optionally tag a section with @summary.

  2. The preview opens and updates

    The right panel shows your resume with changed words highlighted so you can see exactly what moved.

  3. Accept or reject

    Use Accept when the text matches what you would send, or Reject and re-ask with tighter instructions.

  4. Save

    Hit Save in the header to persist the document. Until then, the preview is just staging.

Try these prompts

›

Rewrite my Tailorly experience bullet using STAR format, keep the numbers truthful.

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Add Python and AWS to @skills and group them under a “Cloud & Backend” heading.

›

Update my professional summary and tighten the bullets in my experience section for a product role.

Targeting a role

Tailoring & ATS scoring

When you point Tailorly at a specific posting, it can align your whole resume to that role and produce an ATS-style read of how well it would pass automated screening — with the exact keywords you are missing.

Full-resume tailoring

Paste the job description and state the target title or level. Tailorly mirrors important themes from the posting while keeping your facts accurate, then shows a tailored draft you can accept.

ATS analysis card

Get an overall score, keyword match, and section-by-section breakdown with matching and missing keywords plus suggested changes. You can export it as an ATS report PDF.

Step by step

  1. Paste the posting

    Drop the full job description into chat and name the target role, or use /tailor and /ats.

  2. Review the ATS card

    See the score, the keywords you match, and the ones you are missing — without buzzword stuffing.

  3. Accept the tailored draft

    The preview switches to the tailored version. Follow up with smaller edits to shorten or adjust tone.

  4. Export when ready

    Download the tailored resume (Premium) or the ATS report PDF.

Try these prompts

›

Tailor my entire resume to this posting — keep facts accurate and mirror important themes from the JD. [paste job description]

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/ats @jobdescription [paste the full posting here]

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What keywords and themes am I missing for this job without stuffing buzzwords? [paste JD]

Tailored exports are a Premium feature

Free accounts can tailor and preview. Downloading the tailored resume requires Premium; exporting your base resume and the ATS report is available on Free within the monthly export limit.

Decide where to apply

Fit scoring & the agentic worker

Before you spend time on an application, Tailorly can give a deep, honest read on whether a role is worth it. The fit view goes beyond a single number into a category-by-category breakdown, the matches a recruiter will love, and the gaps that might worry them.

Overall + category scores

A hero match percentage backed by rings for skills, experience, education, and more.

Strengths and gaps

Concrete lists of what aligns strongly and what is missing, in plain language.

Recommendations

Specific tailoring moves and a clear call: apply now, tailor first, treat as a stretch, or pivot.

Recruiter-scan view

What a human will notice on a six-second skim versus what an ATS will rank.

Try these prompts

›

How well does my resume match this job? Here is the posting: [paste full job description].

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Is this role a stretch for me on paper? Separate real skill fit from how the resume presents me. [paste JD]

Automation

The auto-apply agent

For supported postings, Tailorly can open a real browser and work through the application for you — filling fields from your resume, asking you the questions only you can answer, and pausing for your approval before it submits.

Step by step

  1. Start the agent

    Say “Apply to this job for me” on a job, or use Apply with agent in the job detail view. Pick which resume to use if you have several.

  2. Watch it work live

    A browser preview panel opens with the live session. You can see each step the agent takes.

  3. Answer inline questions

    When the form needs something specific (work authorization, salary, custom questions), the agent asks you right in chat.

  4. Approve before submit

    The agent pauses at a review gate so you confirm everything is correct before the final submit.

  5. Track the outcome

    Confirmed applications flow into your job tracker so you always know where you applied.

Did you apply?

Whenever you open an apply link or run the agent, Tailorly asks a simple Applied / Not applied follow-up so your tracker stays accurate. Resolving it unblocks the rest of the chat.

Your public presence

Tailorly profile & portfolio

Turn the resume you already maintain into a polished public profile or a full portfolio website — no separate content to write. Because it reads the same resume, your public page stays aligned with your latest experience and positioning.

Guided builder

Tailorly walks you through your profile, about, experience, projects, skills, education, and certificates, then previews the page in the panel.

AI website builder

Describe the site you want and Tailorly generates a styled page from your resume that you can publish at your own username.

Step by step

  1. Ask to build it

    For example, “Build a portfolio website from my resume.”

  2. Pick a resume and username

    Choose the source resume and the slug your public page will live at.

  3. Walk the sections

    Confirm or adjust each section; the preview updates as you go.

  4. Publish

    Toggle publish and share your public link. Edit any time — it re-reads your resume.

Getting started

Create a resume from scratch

New to Tailorly or starting a fresh resume? A guided, conversational wizard builds one with you — or you can upload an existing PDF / DOCX and Tailorly extracts it straight into a live preview.

Two ways to start

Upload an existing resume

Drop a PDF or DOCX (up to 10MB). Tailorly parses it into structured sections you can immediately edit and tailor.

Start from scratch

Answer one step at a time — personal info, summary, experience, education, skills, projects, certificates — with the preview building live beside you.

Step by step

  1. Choose upload or scratch

    From onboarding, the sidebar, or Create resume.

  2. Fill in each section

    The wizard asks for one thing at a time so it never feels like a giant form.

  3. Watch the preview build

    Each answer appears in the rendered resume on the right.

  4. Finish into the workspace

    Tailorly saves the resume and drops you into the dashboard, ready to edit, tailor, and apply.

Application materials

Cover letters

Tailorly drafts and revises cover letters in the same chat, grounded in your resume and the role you are targeting. Letters are treated separately from your resume summary, so asking for one never touches your resume.

  • Write a new letter for a specific role, or revise an existing draft in place.
  • The draft appears in the preview panel just like a resume — review before you keep it.
  • Accepted letters are saved and can be reopened later from your home hub.
  • Export to PDF or DOCX when you are ready to attach it.

Try these prompts

›

/coverletter Write a cover letter for this product manager role using my resume. [paste JD]

›

Make the opening paragraph of my cover letter more specific to the company's mission.

Send it out

Exports

When a document matches what you would send, export it from the preview header. Tailorly produces ATS-safe files using clean, standard formatting.

Resume PDF & DOCX

Download from the preview header. Free includes a monthly export allowance; Premium is unlimited.

Cover letter PDF & DOCX

Export accepted cover letters in the same place.

ATS report PDF

Export the ATS analysis card as a shareable report.

What needs Premium

Tailored-resume downloads require Premium. Base resume exports work on Free within the monthly limit, and cover-letter exports are available to everyone.

Reference

Resume pieces you can name in chat

No special syntax is required — just say the section name in a normal sentence. You can also tag a section explicitly with an @tag when you want to be precise.

@profile

Name, title, email, phone, location, LinkedIn, GitHub.

@summary

Your professional summary paragraph.

@experience

Roles, companies, dates, descriptions, and bullets.

@projects

Project name, description, technologies, and links.

@skills

Grouped or flat skill lines.

@education

Degree, school, and year.

@certificates

Certificate name, issuer, and date.

job context

Paste a posting when you want match scoring or tailoring.

Power users

In-chat help & shortcuts

Plain sentences are enough for everything. If you prefer shortcuts, a handful of slash commands route directly to a workflow. Type /help in the workspace any time for the compact reference.

/help

Show the quick reference of commands and section tags.

/tailor

Tailor your resume to a pasted job and show the ATS card.

/edit

Edit a named section, e.g. /edit @summary …

/add

Add new content, e.g. /add @projects …

/ats

Run an ATS analysis against a pasted job description.

/coverletter

Generate or revise a cover letter for a role.

Plans

Plans & limits

Both tiers share the same agentic workspace. Premium adds a much larger Tailorly AI allowance for longer sessions, a public profile, and clearer usage on your account.

Free

  • Full workspace: advice, editing, tailoring, job search, fit scoring.
  • Monthly included Tailorly AI for steady use.
  • 30 job searches per month (filtering stays available after the cap).
  • Monthly base resume exports; tailored downloads need Premium.

Premium

  • Everything in Free, with a much larger Tailorly AI allowance.
  • 30 job searches per day for heavier sessions.
  • Unlimited resume exports, including tailored downloads.
  • Public Tailorly profile and usage shown on your account.
See full pricing

Get more out of it

Tips

Separate coaching from edits

Ask for feedback first; once you agree with the plan, send a follow-up that says exactly what to change.

Paste job descriptions once

Put the full posting in one message, then refer to “the posting above” in follow-ups to keep context.

Be explicit about truth

Say when metrics must not be invented, or when employers and dates must stay fixed.

Scope clearly

Name the section and whether you mean every entry or only your current role.

Review before saving

Treat the preview as staging — only save when the document matches what you would send.

Ready to try it on your own resume?

Open the workspace and ask for anything in plain English — Tailorly handles the routing.

Open the workspace