Your team will use an AI assistant this year. The only real question is whether the business chooses it — with a data policy, an owner and a budget — or whether staff choose it themselves on free consumer accounts, which is how customer data ends up in tools nobody vetted. This comparison is the SME buyer's version of that choice: three serious options, priced within a few dollars of each other, that win in clearly different situations.
The contenders and the prices (verified August 2026)
ChatGPT Team (OpenAI): $25 per user per month, or $20 on annual billing, with a two-seat minimum. Claude Team (Anthropic): $25 per user per month, $20 annual, with a five-seat minimum. Microsoft 365 Copilot: the standard licence is $30 per user per month, and a newer Business tier is $21 on annual billing ($25.20 monthly), currently promoted at $18 until 30 September 2026. The Copilot number carries an asterisk the others do not: it stacks on top of a qualifying Microsoft 365 subscription — it is an add-on, not a standalone product — so the true per-head cost of "AI in your Office apps" includes the Office apps.
Where each one wins
Microsoft 365 Copilot — when the business genuinely lives in Microsoft 365. It is the only assistant that works inside the Outlook, Excel, Teams and Word you already pay for, grounded in your own tenant's emails, files and meetings. For drafting replies in context, summarising the meeting you missed, or interrogating a spreadsheet without exporting it, that placement is decisive. The honest caveat from implementation experience: Copilot inherits your permissions model. If your SharePoint and file sharing have grown organically for a decade, Copilot will cheerfully surface documents people technically had access to but never knew existed. Governance work belongs in the budget alongside the licences.
Claude Team — when the work is writing, analysis and judgement over long documents. Contracts, reports, proposals, policy documents, research synthesis: this is where Claude's long-context handling and writing quality lead in our use, and why professional-services firms disproportionately pick it. It is the least feature-sprawling of the three — fewer toys, strong core — which some teams experience as focus and others as thinness.
ChatGPT Team — when the use case is still "a bit of everything". The broadest feature surface (voice, image generation, custom GPTs, data analysis), the fastest release pace, and the assistant most of your staff already know from home. As a first, general-purpose deployment it is the lowest-friction default, and familiarity genuinely matters for adoption.
Data and privacy for business use
The business tiers of all three exclude your prompts and data from model training by default and offer admin controls and standard contractual terms — this, not features, is the core reason to pay for business seats rather than tolerating free personal accounts. The risk sits elsewhere: staff using free consumer tiers with customer data (a policy problem you must write down, not assume), and — specific to Copilot — tenant permission sprawl, as above. Whatever you pick: write a one-page policy stating what data may and may not go into an assistant, get the DPA reviewed like any other processor, and treat EU/UK data-residency requirements as a checklist item, not a footnote.
You need one, not three
The arithmetic that matters is not $20 versus $25 — it is utilisation. Ten licences used twice a week cost more per useful hour than three licences used daily. Our standing advice: pick the one assistant that fits your dominant work pattern, buy seats for the team that actually asked, and expand on evidence. Running two "to compare" for a quarter is defensible; running three because departments chose independently is how SME software budgets die.
Deployment advice from the field
- Start with the team that asked. Enthusiasm is the scarcest deployment resource; do not spend it on conscripts.
- Write the data policy before the first login — what may go in, what must not, and where the assistant's output needs human review.
- Appoint a champion and build a prompt library. Twenty minutes a week of shared "here is what worked" beats any vendor training.
- Review usage at 60 days and cut idle seats without guilt. The vendors make this easy to check; most buyers never look.
- Re-tender annually. This market reprices and re-ships quarterly; the right answer in August 2026 has no tenure.
Assistants answer; automation acts
One structural point before you budget: a chat assistant helps the person using it, one conversation at a time. The larger SME wins usually come from AI inside automated workflows — classifying every enquiry, extracting data from every invoice, drafting every follow-up — which is automation-platform territory rather than assistant territory. Our AI and automation stack guide covers that architecture; if your team leans technical and self-hosting appeals, the open-source platform below is where assistant licences and workflow automation meet.
The open-source automation platform built for AI-agent workflows
Best for: Technically capable SMEs and teams building AI-in-the-loop workflows that want Make-class power without per-step metering — or without licence fees at all.
Choosing an assistant and wiring AI into your processes are different projects with different economics. If you want an honest view on where AI would actually pay back in your business — before buying licences for everyone — that is exactly the work we do.
Sources & further reading
- Microsoft 365 Copilot — Copilot plans and licensing requirements (accessed Aug 2026)
- OpenAI — ChatGPT pricing — Team/Business per-seat prices (accessed Aug 2026)
- Anthropic — Claude plans — Team plan pricing and seat minimums (accessed Aug 2026)
- Epic IT — ChatGPT vs Copilot vs Claude for business — corroborating SME-lens comparison