Spearworks AI
Free consult

From Pavilion On the Bench, October 27, 2026

Which AI can hold your job search files?

A saved assistant keeps your files and instructions, so every chat starts already knowing you. For a job search, that means your master resume, how you write, your rules, and a scorecard for which roles are worth your time. All four big AI companies have one. Here is what each calls it, whether the free plan is enough, and what happens to the files you upload.

Checked against each vendor's own pages on October 25, 2026. Every cell links to its source. Prices and plans change often, so click through before you buy.

Gemini

Google

What it's called
A skill (Gems end November 17)On personal Google accounts, Gems turn read-only November 17, 2026 and disappear December 17. Google recreates them as skills. Work accounts keep Gems until March 2027.Gems to skills
Can you build one free?
YesSkills need no Google AI subscription. You must be 18 or over and have Keep Activity on.Create skills in Gemini
Files it can hold
Plain-text files, 100 MB in total.md and .txt work. Word and Excel files don't.Create skills in Gemini
Instructions box
Yes, that's what a skill isSaved instructions you can call by typing / and the skill's name in any chat.Gems to skills
Where you set it up
Web, Mac app and phone appCreate skills in Gemini
Personal plan if you outgrow free
Google AI Pro, $19.99/monthAI Plus is $4.99/month. You don't need either for skills.Gemini subscriptions
Does it learn from your uploads?
Yes, while Keep Activity is onOn by default for adults, and skills require it. Some chats are read by human reviewers. Turning it off stops training but also turns off skills.Gemini Apps privacy hub Manage Gemini activity
What we saw building one
Built a Gem on a work account; it answered from all five filesAbout 40 seconds per answer on the Pro model. We haven't tested skills: they aren't on work accounts yet.
Our pick if you...
...live in Gmail and Google Docs and want it free.

ChatGPT

OpenAI

What it's called
A projectPersonal accounts can no longer create custom GPTs, and OpenAI is retiring GPTs.Projects in ChatGPT Creating and editing GPTs
Can you build one free?
Yes, up to 5 filesExactly enough for the five files below.Projects in ChatGPT
Files it can hold
Free 5, Go and Plus 25 per projectUp to 10 at a time, 512 MB per document. OpenAI lists DOCX, PDF and TXT; our .md files uploaded fine.Projects in ChatGPT Uploading files to ChatGPT
Instructions box
Yes, in Project settingsOverrides your account-wide instructions inside the project.Projects in ChatGPT
Where you set it up
Web, plus the desktop and phone appsWe built ours on the web.Projects in ChatGPT
Personal plan if you outgrow free
Go $8/month, Plus $20/monthBoth allow 25 files per project.ChatGPT pricing Projects in ChatGPT
Does it learn from your uploads?
Yes, unless you turn it offOn by default for Free, Plus and Pro, and it covers project files. Settings, Data controls, Improve the model for everyone.Data controls in ChatGPT Projects in ChatGPT
What we saw building one
Free plan; it answered from all five filesSet the project's memory to Project-only so your other chats stay out of it.
Our pick if you...
...already use ChatGPT and want the free option.

Claude

Anthropic

What it's called
A projectWhat are projects?
Can you build one free?
Yes, up to 5 projectsOne Anthropic page says project instructions are for paid plans only. If you don't see the box, upload your instructions as a sixth file.What are projects? Claude personalization features
Files it can hold
30 MB per file, as many as fitPaid plans expand capacity up to 10 times. Anthropic's list doesn't name .md, but ours uploaded fine.Upload files to Claude What are projects?
Instructions box
Yes, paid plans per one Anthropic pageOther Anthropic pages list no plan limit.Claude personalization features What are projects?
Where you set it up
claude.ai on the webAnthropic doesn't list which apps support projects. We built ours on the web.
Personal plan if you outgrow free
Pro, $20/month$17/month billed yearlyclaude.com/pricing
Does it learn from your uploads?
Your choice, set at signupSettings, Privacy, Help improve our AI models. On keeps chats up to 5 years; off, 30 days.Consumer terms update Model improvement setting
What we saw building one
Max plan; it answered from all five filesIt also follows the preferences in your Claude profile, so check those don't clash.
Our pick if you...
...care most about writing that sounds like you.

Copilot

Microsoft

What it's called
A notebookGet started with Notebooks
Can you build one free?
No, needs a Microsoft 365 planPersonal, Family or Premium. Microsoft 365 Basic has no AI features.Copilot Notebooks FAQ Microsoft 365 plans
Files it can hold
Uses up to 300 filesMicrosoft lists Word, PowerPoint, Excel, PDF, .txt and .rtf; our .md files uploaded fine. No size limit published.How Copilot Notebooks works Add references to a notebook
Instructions box
Yes, under the ... menuNotebook instructions
Where you set it up
Web, at m365.cloud.microsoftGet started with Notebooks
Personal plan if you outgrow free
Personal, $9.99/monthFamily $12.99, Premium $19.99. On Family, the AI features are for the owner only.Microsoft 365 plans AI usage in Microsoft 365
Does it learn from your uploads?
NoMicrosoft: Notebooks don't use your data to train the model.Copilot Notebooks FAQ
What we saw building one
Family plan; it answered from all five filesCopilot opens whichever Microsoft account you used last. Check the corner says Personal, not a work account.
Our pick if you...
...already pay for Microsoft 365 and don't want your files used for training.
  • Yes
  • With conditions
  • Not yet
  • Not confirmed

Both moved this fall: Google is replacing Gems with skills, and OpenAI is retiring custom GPTs. Keep your five files somewhere you control, so you can move them when a tool changes. Gems to skills ↗

Five files, any of the four

The tool matters less than what you put in it. Build these once, upload them, and every application starts from your real facts.

  1. 01Master ResumeEvery fact about your career, with numbers. The AI writes only from this.
  2. 02Voice and StyleHow you write, and the words you never use.
  3. 03Ground RulesWhat it must always do, must never do, and a check before it hands anything over.
  4. 04Personal HighlightsThe human details that get you remembered.
  5. 05Role ScorecardYour rules for whether to apply at all, checked before it writes a word.

One rule: draft from the files, never from memory. If a number isn't in your master resume, it doesn't go on a resume.

Spearworks AI

Want this workshop for your group?

I teach this build live for career groups, chambers and teams, and set up saved assistants for small businesses that want the same thing for proposals, client emails or onboarding.

Book a free consult

Nathan Spear · spearworksai.com

Spearworks Labs · All comparisons · Checked October 25, 2026. Not affiliated with any vendor listed.