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Claude first, ChatGPT second, Copilot when it's easiest.

What each plan costs, how much use you really get, and which one fits your business.

Glossary

Our order of recommendation

  1. Start here

    Claude

    Team for 2 to 150 people · Enterprise above 150 or for compliance

    The strongest writer and reader of the three: whole contracts, tax files and policy manuals in one conversation, careful answers, and Claude Code included, to work through folders of your documents or build small tools.

    Choose it when your work is documents, spreadsheets, writing and analysis, or you want to build small internal tools.

    $20 a person a month, billed yearly

  2. Strong second

    ChatGPT Business

    2 to 200 people

    The broadest toolbox: image generation, voice, meeting notes on the Mac app, custom GPTs and everyday chat that is effectively unlimited.

    Choose it when people want images, voice and quick everyday answers more than deep document work.

    $20 a person a month, billed yearly

  3. When it's easiest

    Microsoft Copilot

    Copilot Business, up to 300 people

    Lives inside Outlook, Teams, Word and Excel and already knows your email, files and meetings. It also runs Claude models for some of its work.

    Choose it when your whole office runs on Microsoft 365 and you want the least change for staff, or Teams meeting recaps matter most.

    $21 a person a month plus your Microsoft 365 plan

Find your plan

Your email and files live in
Most of the work is
You handle patient health information

We would start you on

Claude Team

Anthropic

Claude Team is our default: same price as ChatGPT Business, the strongest at long documents and careful writing, works with Microsoft 365 and Google Workspace, and includes Claude Code. It covers 2 to 150 people; use the Team or Enterprise check below if you need audit logs, HIPAA coverage or invoicing.

8 people: about $160 · a year: $1,920

Is it worth it?

A seat costs the same whatever it does. Here's how little time it has to save to pay for itself, in your numbers.

Plan

billed yearly

Each seat pays for itself at 6.2 minutes a week

Each seat pays for itself at

6.2minutes a week

Seats a month
$240
Time saved a month
$2,835
Net a month
$2,595

Arithmetic, not a promise: 21 working days and 4.33 weeks a month. The real time saved is what a pilot measures. Claude Enterprise adds usage on top of the seat, so its break-even depends on use.

A day of work: which does what best

Our take from daily use and the vendors' documentation, not a lab test. The independent Vals Index (November 2026), which tests the underlying models on finance, legal, tax and coding work, ranks Claude Sonnet 5.5 first.

  • Read a 300-page contract or tax file

    Claude reads about 1,250 pages at once (PDFs up to 1,000 pages); Copilot caps files at 50 MB.

    • Claude Best
    • ChatGPT Business Strong
    • Microsoft Copilot Good

  • Write a proposal, policy or client letter

    Claude writes most naturally and learns your tone from examples.

    • Claude Best
    • ChatGPT Business Strong
    • Microsoft Copilot Good

  • Analyze or build a spreadsheet

    Claude for Excel keeps formulas intact and cites the cells it used; Copilot edits in place inside Excel.

    • Claude Best
    • ChatGPT Business Strong
    • Microsoft Copilot Strong

  • Research with sources

    Claude Research and ChatGPT deep research both cite sources; Copilot Researcher adds your internal files.

    • Claude Best
    • ChatGPT Business Best
    • Microsoft Copilot Strong

  • Build a small dashboard or tool

    Claude Code is included in every Team seat; Codex is metered on Standard seats; Copilot's builders are metered or in preview.

    • Claude Best
    • ChatGPT Business Strong
    • Microsoft Copilot Good

  • Find something in company files

    Copilot searches all of Microsoft 365 by default; Claude and ChatGPT reach it through connectors.

    • Claude Strong
    • ChatGPT Business Strong
    • Microsoft Copilot Best

  • Work inside Outlook and Teams

    Copilot is built in; Claude's Outlook add-in is in beta.

    • Claude Good
    • ChatGPT Business Good
    • Microsoft Copilot Best

  • Meeting notes

    Copilot recaps Teams meetings; ChatGPT records on the Mac app; Claude has no meeting recorder.

    • Claude Limited
    • ChatGPT Business Good
    • Microsoft Copilot Best

  • Images and graphics

    Claude makes charts and diagrams but not photos or illustrations.

    • Claude Limited
    • ChatGPT Business Best
    • Microsoft Copilot Strong

Every plan, in detail

Side by side

FeatureClaude TeamClaude EnterpriseChatGPT BusinessMicrosoft Copilot
Price per seat$20 yearly, $25 monthly$20 yearly + usage$20 yearly, $25 monthly$21 yearly + Microsoft 365
Heavy-user seat$100 / $125Billed as usage$100 / $125One seat type
People2 to 15020 minimum2 to 200Up to 300
CommitmentMonthly or yearlyOne yearMonthly or yearlyMonthly or yearly
Usage1.25× Pro per 5 hours, plus weeklyNo caps; pay per useChat unlimited; agents meteredNo published cap; some agents per use
Reads at onceAbout 1,250 pagesAbout 1,250 pagesAbout 320 pages (reasoning); about 40 (Instant)50 MB per file
Works insideExcel, Word, PowerPoint, Outlook (beta), ChromeSame as TeamExcel, Word, PowerPoint, Google SheetsWord, Excel, PowerPoint, Outlook, Teams
Building toolsClaude Code includedClaude Code, billed as usageCodexCopilot Studio; Code per use
Image generation
Meeting notesMac appTeams recap
Trains on your dataNoNoNoNo
Single sign-onYour Microsoft sign-in
Audit logs and retention controlsThrough Purview
HIPAA business associate agreementYes; not web search
PaymentCardCard, ACH or invoiceCardMicrosoft billing
Nonprofit price$8 a seatThrough salesUp to 75% off, through salesAsk Microsoft
Claude Team or Claude Enterprise?Only matters above 150 people, or if you need HIPAA cover, audit logs, invoices or US-only processing. Open the check.

Claude Team or Claude Enterprise?

Two things decide it: how many people, and whether you need a control only Enterprise has. Both cost $20 a seat. The difference is that a Team seat includes the usage and an Enterprise seat doesn't, so for ordinary office use Team is usually the cheaper of the two.

  • 2 to 19: Team

    Enterprise starts at 20 seats. Team is the plan, unless you need something below, in which case you pay for 20.

  • 20 to 150: your choice

    Both are open to you. Choose Enterprise only if you tick a need below; otherwise Team is usually cheaper.

  • 151 and up: Enterprise

    Claude Team stops at 150 people. Above that, Enterprise is the only Claude plan.

Tick anything you need

Verdict

Claude Team

Claude Team covers you. Same $20 seat, usage included up to the 5-hour and weekly limits, and you can upgrade to Enterprise later without losing a single chat or project.

Claude Team, per year
$8,400
Claude Enterprise seats, per year
$8,400 + usage

Team assumes Standard seats billed yearly; Premium seats for heavy users are $100 a month billed yearly, $125 monthly. Enterprise usage is billed on top at API rates; see the estimate under the models below.

The models, and what Enterprise usage costsWhich model does what, per-token prices, and an estimate for Claude Enterprise, where usage is billed on top of the seat.

The models inside each plan

Each assistant gives you several models: a fast one, an everyday one and one for hard problems. Prices are per million tokens in and out, the rate Claude Enterprise usage is billed at. A page of text is roughly 800 tokens.

Claude

Team and Enterprise

  • Sonnet 5.5$2 / $10

    The everyday model. Fast, strong writing and analysis; what most people should use most of the time.

    Every seat

  • Opus 5.5$4 / $20

    For hard problems: complex analysis, long reasoning and tricky documents.

    Every seat; uses the allowance faster

  • Haiku 5.5$0.10 / $0.50 (over 100,000 tokens: $0.50 / $2.50)

    Fastest and cheapest, for quick answers and high-volume work.

    Every seat

  • Fable 5.2$8 / $40

    Anthropic's most capable model, for the hardest work.

    Premium: up to half the weekly allowance · Standard: paid credits

All four read up to 1 million tokens at once; Haiku costs five times as much on any request over 100,000 tokens. On Team the usage is included in the seat; on Enterprise it's billed at these rates, with 50% off batch work and repeated documents billed at a small fraction through caching.

ChatGPT Business

Standard and Premium seats

  • GPT-6

    One model with effort levels, from Instant for quick chat to Extra High for careful reasoning.

    Every seat; Instant effectively unlimited, higher effort metered

  • GPT-6 Pro

    The deepest reasoning, for the hardest questions.

    15 a month on Standard · 50 a week on Premium

  • Codex

    OpenAI's coding agent, for building tools and scripts.

    Every seat; metered every 5 hours on Standard

On ChatGPT Business you pay per seat, not per token.

What Claude Enterprise usage might cost

An Enterprise seat includes no usage, so the real question is what people use. Pick a model and a type of user for a rough monthly figure per person.

Model they mostly use
Kind of user

Estimated usage per person

$39usage / month

+ $20 seat = $59 per person a month. A Claude Team seat is $20 with usage included, up to its limits.

Illustrative, not a quote: 21 workdays, Anthropic's list prices, no caching discount (caching lowers real bills), Haiku at its rate for requests under 100,000 tokens. Claude Code users average about $13 per active day and $150 to $250 a month, per Anthropic. Add 10% for US-only processing. We size it properly with a two-week pilot and the usage report.

Questions people ask before they buy

How accurate is it? Can we trust what it says?

AI is very good at drafting, summarizing and organizing, and it still gets specific facts, figures and citations wrong, especially ones you did not give it. Give it your source material, ask it to show where answers come from, and have a person check anything that leaves the building. Your business stays responsible for what it sends.

Can we start small and grow?

Yes. Claude Team and ChatGPT Business start at two people. Claude Team upgrades to Enterprise in place, keeping every member, chat and project. Add seats any time; removing them takes effect at renewal.

Is our data used to train the AI?

No, on all four business plans, by default. With Claude, the exceptions are if someone sends thumbs-up or thumbs-down feedback, or the company opts in.

Where is our data stored?

Claude stores data in the US, and Enterprise can keep processing in the US too. Copilot stores data in your Microsoft 365 region, which is the US for US companies. ChatGPT's data residency options are Enterprise only.

How long are chats kept?

Claude Team keeps chats until someone deletes them; they leave Anthropic's servers within 30 days. Claude Enterprise lets you set retention, from 30 days. Copilot follows your Microsoft Purview retention rules.

What happens when someone leaves?

Remove them in the admin console and access stops immediately. Claude lets the owner export the organization's data. ChatGPT Business keeps a departed member's chats; the owner can't browse them but can export that member's data from the Members page. Copilot data stays in your Microsoft tenant.

Can staff keep their personal ChatGPT or Claude accounts?

Not for work. Personal plans run on consumer terms and may train on what people type. Claude can move a personal account into the company workspace, one way, and Microsoft admins can turn off consumer Copilot sign-in. Blocking personal ChatGPT or Claude at the network needs an Enterprise plan, so the AI policy does that work.

Does Claude work with our Microsoft 365 email and files?

Yes. The Microsoft 365 connector reads SharePoint, OneDrive, Outlook and Teams after a one-time approval by your Microsoft admin, and Claude has add-ins for Excel, Word and PowerPoint, with Outlook in beta.

Doesn't Copilot already use Claude?

Partly. Microsoft runs Claude models inside Copilot for some tasks, on by default for US businesses. You get Claude's full experience, including Projects, Claude Code and long documents, only in Claude itself.

Do we need HIPAA coverage?

Only if you put patient health information into it. Then you need a signed business associate agreement: Claude Enterprise and Microsoft Copilot have one; Claude Team and ChatGPT Business don't.

Is there a free trial?

Copilot has a one-month trial that turns into a paid subscription. Claude Team has no trial, so we usually start a client on monthly billing for the first month or two.

Does it work on phones and offline?

All three have phone apps. None works offline. Claude's Office add-ins don't run on iPad, Android or Outlook mobile.

Can we use more than one?

Yes, and it's common: Copilot for everyone in a Microsoft office, plus Claude seats for the people who work through long documents or build tools. We help you avoid paying twice for the same thing.

We already have Copilot Chat or Gemini. Isn't that enough?

For a first safe step, yes: it's the Essentials stack, and it beats personal accounts. It reads less at once and can't build tools, so move to a paid seat when people outgrow it.

What if it goes down?

Outages happen, usually for minutes or a few hours; check status.claude.com or status.openai.com. Keep templates and finished work in your own files, not only in chats, and never leave AI-dependent work for deadline day.

Prices and limits from Anthropic's, OpenAI's and Microsoft's own pricing and help pages, checked November 9, 2026, in US dollars before tax. They change often; we confirm current numbers before you buy. Task ratings are our judgment.

Rather talk it through?

Book a call. Caleb will point you to the right plan and the first project for your business.

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