AI at work

Which AI ecosystem should a small business live in?

Every big vendor now sells an AI that lives inside the tools you already pay for, or wants to become the tool you pay for. The real question for a small business is not which chat is smartest this month. It is which ecosystem your email, files and calendar already sit in, and what each assistant can reach from there.

Checked against each vendor's own pages on October 16, 2026. Every cell links to its source. Prices and plans change often, so click through before you buy.

Microsoft Copilot

Microsoft 365

Business seat price
$23.50 user/month, paid yearly (M365 Business Standard with Copilot)Monthly billing is $28.20 user/month. The Copilot Business add-on is $18.00 user/month paid yearly (list $21.00, $25.20 monthly), with a discount offer between July 1, 2026 and December 31, 2026, and needs a qualifying Microsoft 365 plan. Teams features need a Teams license.Microsoft Copilot plans and pricing
Needs their office suite?
Paid tiers need a Microsoft 365 license. Free chat works with a work account.The pricing page says without Copilot licenses you can still try Copilot Chat by signing in with a work account.Microsoft Copilot plans and pricing
Works inside your email
Yes: drafts emails and summarizes threads in Outlook (Copilot in Outlook)Pricing page lists Copilot in Outlook as included in Business Standard with Copilot. The Outlook help page applies to Outlook for Windows (classic and new), Mac, Android and iOS; it does not list Outlook on the web. Gmail is not named.Welcome to Copilot in Outlook Microsoft Copilot plans and pricing
Works inside documents and spreadsheets
Yes: Word, Excel, PowerPoint, OneNote; Cowork creates Word, Excel, PowerPoint, PDF filesCowork can also edit existing Word, Excel and PowerPoint files stored in OneDrive or SharePoint. Google Docs and Sheets are not named.Copilot Cowork common questions Microsoft Copilot plans and pricing
Meeting notes
Yes: Copilot in Teams meetings; AI recap needs Copilot or Teams PremiumPricing page says a Teams license is required for Copilot in Teams. Transcription is required for Copilot to answer questions after a meeting ends. Intelligent recap is part of the Microsoft Copilot license and of Teams Premium.Catch up on meetings with Microsoft Copilot i...
Runs a multi-step job for you
Yes: Copilot Cowork runs multi-step tasks across apps, metered billingPricing table shows Copilot Cowork as Metered. The Cowork FAQ says billing is usage-based, with admin-set limits per user or group, and that Cowork asks approval before sensitive actions like sending email or posting in Teams.Copilot Cowork common questions Microsoft Copilot plans and pricing
Connects to other business apps
Yes, partly: Microsoft Graph connectors and agents, and Cowork plugins that add skills and connectors; no third-party app names listedThe privacy page says Copilot can reference third-party tools via Graph connectors or agents. The Cowork FAQ says plugins from the Microsoft 365 App Store add new skills and connectors, and admins control them. Neither page names HubSpot, Slack or Google Drive. The pricing-page phrase about Copilot connectors was not found in my fetch.Data, Privacy, and Security for Microsoft Cop... Copilot Cowork common questions
Trains on business data?
Yes: prompts and Graph data are not used to train foundation modelsCovers Microsoft 365 commercial customers. Admins can turn on Anthropic or OpenAI models as subprocessors, and additional terms may apply. The page says Microsoft 365 Copilot is now named Microsoft Copilot.Data, Privacy, and Security for Microsoft Cop...
Where it runs
Web, Windows, Mac (macOS Sonoma 14 or later), iOS and Android mobile appsThe download page lists Windows, Mac (Requires MacOS Sonoma 14 or later) and a mobile app for iOS and Android, but does not use the words iPhone or Android as labels. The Cowork FAQ names the Copilot mobile app for iOS and Android (iPhone, iPad, Galaxy), the browser at copilot.cloud.microsoft, and the Windows and macOS desktop apps. No iOS version or Apple chip requirement found.Download Microsoft Copilot App Copilot Cowork common questions
Our pick
The pick for a business already on Microsoft 365: Outlook, Word, Excel and Teams recap in one seat, with Cowork metered on top. Nothing to install, one admin switch.

Google Gemini

Google Workspace

Business seat price
$14 per user/month for Workspace Business Standard on an annual commitment ($16.80 per user/month billed monthly), per the AI page. The pricing page shows $14 and says 'All plans billed monthly', so the two pages conflict.Pricing page: Starter $7, Standard $14, Plus $22 per user/month, Enterprise 'Let's talk'; 'Save 16% with 1 year commitment' toggle. Intro prices (Standard $7.00, Oct 30, 2026 to Jan 30, 2027, then $14.00) are labeled '50% off for 3 months', but the footnote says 'first 20 users added, for 12 months'. Max 300 users on Starter/Standard/Plus. Price excludes tax.Google Workspace AI tools for business Google Workspace pricing
Needs their office suite?
Sold inside Workspace plans; in-app features need Gmail or Docs.Gemini is sold only as part of Workspace plans on the pages we checked; no standalone business plan or price appears.Google Workspace pricing
Works inside your email
Yes: Gemini in Gmail, on every plan including Starter.Gmail only; Outlook not named. Pricing page lists Gemini in Gmail on Starter.Google Workspace AI tools for business Google Workspace pricing
Works inside documents and spreadsheets
Yes in Docs and Sheets, but only on Standard and up, not Starter.Pricing page lists Gemini in Docs, Sheets, Slides, Drive, Meet and Chat as not supported on Starter (Workspace apps 'Limited'). Word and Excel not named.Google Workspace AI tools for business Google Workspace pricing
Meeting notes
Yes: AI meeting notes in Meet, on Standard and up.AI page lists the Business Standard feature set as 'AI notetaking, translated captions, noise cancellation, and recordings'. Pricing page shows Gemini in Meet not supported on Starter. Teams not named.Google Workspace AI tools for business Google Workspace pricing
Runs a multi-step job for you
Workspace Studio workflows are listed under Business Standard; custom and partner agents are on Enterprise via Gemini Enterprise.The AI page places Studio under Business Standard. Gemini Enterprise has no price on the pages we checked.Google Workspace AI tools for business Google Workspace pricing
Connects to other business apps
Enterprise agents connect to Microsoft 365, Salesforce, SAP, Jira.Listed under Enterprise (Gemini Enterprise). Slack, HubSpot and MCP are not on the page.Google Workspace AI tools for business
Trains on business data?
Yes: 'Your company data is not used for AI model training or ads.'Privacy hub qualifies it: 'Workspace does not use customer data for training models without customer's prior permission or instruction.'Google Workspace AI tools for business Generative AI in Google Workspace privacy hub
Where it runs
Web and mobile experiences; Gemini for desktop and Gemini in Chrome are named. Android, iOS, Windows and Mac are not named on the page.No device or OS requirements listed.Gemini overview
Our pick
The pick for a Workspace shop, as long as you are on Business Standard or above. Starter gets Gmail help only; Docs, Sheets and Meet notes start at $14.

ChatGPT

OpenAI

Business seat price
$20/user/month, billed annually (2+ users); $25/user/month if billed monthlyFigures match the learn.chatgpt.com pricing page. Any Premium seat tier is not confirmed.ChatGPT pricing
Needs their office suite?
No. Its own workspace, connecting to Google Workspace, Slack, GitHub and Microsoft 365Business plan page lists 'Connect to Google Workspace, Slack, GitHub, Microsoft 365, and more'.ChatGPT Business pricing
Works inside your email
Yes, through connected apps: Google Workspace or Microsoft 365Work tasks can also run when a new Gmail message arrives. Availability depends on plan, workspace and admin settings.Connected apps in ChatGPT ChatGPT Business pricing
Works inside documents and spreadsheets
Yes, partly: Excel, Word, PowerPoint and Google Sheets extensions are listedThe pricing comparison table names the extensions but its per-plan columns did not read cleanly, so check which plan includes them.ChatGPT pricing
Meeting notes
Not publishedNot found on loaded pages.ChatGPT pricing
Runs a multi-step job for you
Yes: ChatGPT Work and Codex on every Business seat; Dots, always-on agents, on Premium seatsStandard seat $20, Premium seat $100 per user per month billed annually. Work tasks can trigger on events in connected apps.ChatGPT Business pricing Connected apps in ChatGPT
Connects to other business apps
Yes: connected apps for Google Workspace, Slack, GitHub, Microsoft 365 and moreApps are installed as plugins under Settings; admins can manage connections centrally. Availability varies by plan, region and role.Connected apps in ChatGPT ChatGPT Business pricing
Trains on business data?
No training on business data by default (Business plan)Stated in the Business plan block of the pricing page.ChatGPT pricing
Where it runs
Desktop and mobile apps for ChatGPT and Codex (per the Business plan description). Specific platforms and browser extension not published on loaded pages.It does not name Windows, Mac, iPhone, Android or an extension.ChatGPT pricing
Our pick
The strongest standalone chat with the widest adoption. Pay for Business, not Plus, so training is off by default and an admin holds the keys.

Claude

Anthropic

Business seat price
Standard $20/seat/month billed yearly ($25 monthly). Premium $100/seat/month billed yearly ($125 monthly).Team needs at least two members; US prices excluding tax; no effective date shown on either page.What is the Team plan? Claude pricing
Needs their office suite?
No. Works on its own account and connects to Gmail, Drive and Microsoft 365.The Team plan page lists Google Drive, Gmail, Google Calendar, GitHub, Microsoft 365 and Slack as optional connections.What is the Team plan?
Works inside your email
Yes. Gmail through the Google connector (search and send) and Outlook mail through the Microsoft 365 connector (read by default).Team owners must enable each connector at the organization level. Microsoft connector is read-only by default until an admin enables write tools.Use Google Workspace connectors Set up the Microsoft 365 connector
Works inside documents and spreadsheets
Yes. Creates Excel (.xlsx), PowerPoint (.pptx), Word (.docx) and PDF files from chat; edits Google Docs, Sheets and Slides live in beta.File creation is available on Team, and owners can disable it. Live Google editing is labeled beta.Create and edit files with Claude Use Google Workspace connectors
Meeting notes
Partial. No built-in meeting recorder. The Microsoft 365 connector can read Teams meeting transcripts.Transcript read permission (OnlineMeetingTranscript.Read.All) is listed; the connector is available on all plans, and a Team owner must enable it first. Claude does not record or join meetings itself on the pages checked.Set up the Microsoft 365 connector
Runs a multi-step job for you
Yes. Claude Cowork runs multi-step tasks on Pro, Max, Team and Enterprise; Claude Code is included in Team.Cloud-based Cowork sessions are in beta on Team and Enterprise.Get started with Claude Cowork What is the Team plan?
Connects to other business apps
Yes. Built-in connectors: Google Drive, Gmail, Google Calendar, GitHub, Microsoft 365, Slack; admin controls cover remote and local connectors.MCP is not mentioned on the Team plan or pricing pages. Team owners must enable each connector.What is the Team plan? Claude pricing
Trains on business data?
No model training on your content by default on Team.Pricing page lists Team as 'None by default'. Not stated on the Team plan support page.Claude pricing
Where it runs
Chat on web, iOS, Android and Desktop (Mac, Windows x64 and arm64; Linux beta on Ubuntu and Debian).Download page lists no minimum OS versions; Mac build is universal (Apple silicon and Intel). Android is on the pricing page only. A Chrome extension was not found on the pages checked.Claude pricing Claude download page
Our pick
The standalone that reaches both ecosystems: Gmail and Drive, or Outlook and Microsoft 365, through connectors you turn on, plus Cowork for multi-step jobs. Our own stack runs on it.

Apple Intelligence

Apple

Business seat price
Included with supported devices; no business seat price publishedSupport page says expanded access for server-based features will cost a fee later; no price given.Apple Support: Apple Intelligence availabilit...
Needs their office suite?
Mostly Apple's own apps. Creator Studio features skip Google and ChatGPT accounts.Keynote, Pages and Numbers intelligence features need an Apple Creator Studio subscription; no price on the page.Apple Support: Creator Studio intelligence fe...
Works inside your email
Apple Mail: summaries and Smart Reply. Outlook drafting announced as coming soon.Mail guide says Apple Intelligence is in beta on M1 or later Macs. Newsroom says users will soon be able to ask Siri AI to draft in Microsoft Outlook. No plan or price stated; Gmail not named.Apple Support: Apple Intelligence in Mail Apple Newsroom: Siri AI
Works inside documents and spreadsheets
Keynote, Pages, Numbers via Apple Creator Studio subscriptionFeatures listed: image and shape generation, Super Resolution and Auto Crop, presentation generation and presenter notes in Keynote (beta), Magic Fill in Numbers. No price on page; general writing in Pages not described.Apple Support: Creator Studio intelligence fe...
Meeting notes
Siri Recap: title and key points after a conversation, in beta late 2026. Not a meeting transcript.Newsroom says Siri Recap arrives in beta later this year, English first, not initially in the EU. No plan named.Apple Newsroom: Siri AI
Runs a multi-step job for you
Siri AI takes actions in apps; Shortcuts chains actions across appsNewsroom gives examples such as texting in WhatsApp and playing a book on Audible. No hand-back agent mode or plan stated.Apple Intelligence
Connects to other business apps
Not publishedPages name no HubSpot, Slack, Drive or Microsoft 365 connector and no MCP. Apple says developers can integrate Siri, Writing Tools and Image Playground, and Siri works with third-party apps.Apple Intelligence
Trains on business data?
Personal data is not used for training by default; users can opt inCovers personal data, not a named business plan. Page says never used unless you explicitly choose to help improve models (opt-in for Siri audio).Apple Privacy: Features
Where it runs
iPhone 16 or later (also iPhone 15 Pro, 15 Pro Max, iPhone Air), iPad M1 or later, Mac M1 or later, Apple Vision ProVision Pro M2 or later is on the apple.com page, not the support page. Some features need Mac M3 or later or iPad M4 or later with 12GB memory. No web, Windows or Android app listed.Apple Support: availability and requirements Apple Intelligence
Our pick
Not a business ecosystem yet. Useful for free on a recent Mac or iPhone for summaries and Mail replies; no seat, no admin, no connectors.

Start from where your files live

The assistant that can see your email, documents and calendar without a setup project wins most of the time. These three checks settle it.

  1. 01Where is the mail?If the business runs on Microsoft 365 or Google Workspace, the built-in assistant already has permission to read it. A separate assistant needs a connector and an admin to turn it on.
  2. 02What needs doing?Summaries and drafts work everywhere. A multi-step job that touches several apps is where the agent features differ, and where the plan tier matters.
  3. 03Who else is on the account?A business seat changes the training default and gives an admin the controls. Personal plans used for work are where the privacy problems start.

Two ecosystems is normal. The suite assistant for the inbox and the documents, and one standalone assistant for the thinking work. Pay for both before you pay for a third.

Spearworks AI

Not sure which one your business already owns?

I look at what you pay for today, turn on the assistant you already have, set the privacy defaults, and show the team two jobs it can do by Friday. One session.

Book a free consult

Nathan Spear · spearworksai.com

Spearworks Labs · All comparisons · Checked October 16, 2026. Not affiliated with any vendor listed.