What a 5-Person Team's AI Stack Actually Costs in 2026

Individual AI subscriptions feel cheap. Team AI budgets are not — because per-seat pricing multiplies every choice by headcount, and because the difference between a standard seat and a premium seat is now bigger than the difference between entire tools. This guide runs the actual first-year math for a five-person team, layer by layer.

How these numbers were sourced: every price below is what the vendor's own pricing page displayed on July 21, 2026 — Cursor, GitHub Copilot, Claude, Jasper, Writesonic, Obsidian, and Grammarly. Several popular vendors are deliberately absent because their public pages could not be independently verified in USD that day: OpenAI and Perplexity could not be re-verified at press time, Notion's page rendered non-USD regional pricing, and Brevo's page did not expose plan prices to verification. We quote nothing we could not read. SaaS prices drift — confirm on the vendor page before you commit a budget.

The verified price sheet

Vendor	Plan	Listed price	Billing note
GitHub Copilot	Pro	$10 per user/month	Monthly pricing shown
Grammarly	Pro	$12/month	2,000 prompts/member/month listed
Cursor	Individual	$16/month annual · $20 monthly	Pro, Pro+, Ultra tier options
Claude	Pro	$17/month annual · $20 monthly	Annual saves $36/year
Claude	Team (standard seat)	$20/seat/month annual · $25 monthly	Minimum is team-based
Cursor	Teams	$32 per user/month annual · $40 monthly	Standard and Premium tiers
GitHub Copilot	Pro+	$39 per user/month	Monthly pricing shown
Obsidian	Commercial license	$50 per user/year	Base app otherwise free
Obsidian	Sync add-on	$4/user/month annual · $5 monthly	Optional
Jasper	Pro	$59/month per seat annual · $69 monthly	Business tier is custom
Writesonic	Starter	$79/month	Annual listed as saving $240/year
Claude	Max	From $100/month	5x–20x Pro usage
GitHub Copilot	Max	$100 per user/month	Monthly pricing shown
Claude	Team (premium seat)	$100/seat/month annual · $125 monthly	The high-usage tier
Writesonic	Basic / Growth	$199 / $399 per month	Annual listed as saving $600 / $1,200 per year

Stack one: the lean team — $3,010 first year

The cheapest coherent five-person stack from the verified sheet: everyone codes with Copilot, shares a Claude Team workspace, and writes through Grammarly, with an Obsidian knowledge base licensed for commercial use.

Layer	Choice	Math	Year one
Coding	Copilot Pro × 5	$10 × 5 × 12	$600
Assistant	Claude Team standard × 5 (annual)	$20 × 5 × 12	$1,200
Writing	Grammarly Pro × 5	$12 × 5 × 12	$720
Knowledge	Obsidian Commercial × 5 + Sync (annual)	$50 × 5 + $4 × 5 × 12	$490
Total			$3,010

That is $602 per person per year — roughly $50 per person per month — for a full four-layer stack. For most small teams this is the honest baseline, and every dollar past it should be justified by a specific bottleneck.

Stack two: the growth team — $5,026 first year

Swap the coding layer to Cursor Teams, keep the Claude workspace, and give the two content-facing people Jasper seats instead of stretching Grammarly.

Layer	Choice	Math	Year one
Coding	Cursor Teams × 5 (annual)	$32 × 5 × 12	$1,920
Assistant	Claude Team standard × 5 (annual)	$20 × 5 × 12	$1,200
Writing	Jasper Pro × 2 seats (annual)	$59 × 2 × 12	$1,416
Knowledge	Obsidian Commercial × 5 + Sync (annual)	$50 × 5 + $4 × 5 × 12	$490
Total			$5,026

Note what moved the needle: the coding layer tripled ($600 → $1,920) and two Jasper seats cost nearly as much as five Grammarly seats twice over. Partial seating — specialized tools only for the people who live in them — is the single best lever in team AI budgeting.

Stack three: the premium team — $13,198 first year

Every seat heavy: Cursor Teams, Claude Team premium seats, a Writesonic Growth workspace for the marketing engine, same knowledge layer.

Layer	Choice	Math	Year one
Coding	Cursor Teams × 5 (annual)	$32 × 5 × 12	$1,920
Assistant	Claude Team premium × 5 (annual)	$100 × 5 × 12	$6,000
Writing/Marketing	Writesonic Growth workspace	$399 × 12	$4,788
Knowledge	Obsidian Commercial × 5 + Sync (annual)	$50 × 5 + $4 × 5 × 12	$490
Total			$13,198

The premium stack costs 4.4x the lean stack. Almost all of that gap is two line items: premium assistant seats ($6,000 vs $1,200) and the specialized marketing platform ($4,788 vs $720). Tool choice barely moves the total; seat tier and specialization do.

The annual-billing table

Annual billing is the quiet discount across the sheet. From the listed prices, for the five-person team:

Line item	Monthly billing/year	Annual billing/year	Saved
Claude Team premium × 5	$7,500	$6,000	$1,500
Writesonic Growth	$4,788 listed	Vendor lists annual saving	$1,200 (as listed)
Claude Team standard × 5	$1,500	$1,200	$300
Jasper Pro × 2	$1,656	$1,416	$240
Obsidian Sync × 5	$300	$240	$60

If you are confident in a tool, annual billing on the premium lines is worth more than most tool-switching decisions. If you are still evaluating, the monthly premium is the price of the exit door.

The hardware alternative worth pricing

Before signing the premium stack, price the one-time alternative: a local-AI laptop at $1,229–$2,150 or a desktop GPU runs open models with zero recurring seat fees. Local models do not replace the frontier tools for most teams — but at $13,198/year, the premium stack costs more every two months than the best laptop in our guide costs once. A hybrid (lean SaaS stack + one local-AI workstation for bulk work) is the arbitrage most teams never run.

For the tool-by-tool reasoning behind these layers, see our AI coding comparison, the writing-tools battle, and the knowledge-tools comparison.

Frequently Asked Questions

Why is ChatGPT missing from these stacks?

Because its public pricing page could not be independently verified in USD on our sourcing date, and this guide quotes nothing it could not read directly from a vendor page. OpenAI publishes ChatGPT plan pricing at openai.com — check it there and slot it into the assistant-layer math the same way the Claude rows work.

Is annual billing always the right call for a team?

No. Annual billing saved up to $1,500/year on a single line in our math, but it converts a monthly decision into a year-long commitment. The pattern that works: monthly billing during the first quarter while seats and usage settle, then annual on the lines the team has clearly adopted.

Do all five people need a seat on every tool?

That is the most expensive assumption in team AI budgeting. Our growth stack cut the writing layer from five seats to two and saved $2,124/year versus seating everyone on Jasper Pro annual. Seat the people who live in the tool; everyone else borrows output.

The Bottom Line

A five-person team can run a real four-layer AI stack for $3,010 a year — and can just as easily sign up for $13,198. The spread is not about picking better tools; it is seat tiers, specialization, and billing cadence. Run the lean stack first, upgrade the specific seat that hits its ceiling, take annual billing only on the lines you are sure of — and price the local-hardware hybrid before anyone signs the premium sheet.