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Choosing a project tool by team size: 5, 20 and 100 people

The same tool that is obviously right for five people is obviously wrong for a hundred. What changes is not the feature list — it is what the tool has to survive.

Rodrigo KrohlingBuilds and runs SaaS Compare solo Reviewed 7 Aug 2026

4 min read

Team size changes the problem, not the requirements

Project tool comparisons usually hold the requirements fixed and vary the features. That gets the relationship backwards. At different sizes you are solving genuinely different problems, and a tool that solves one well often solves the others badly by construction.

At five people, coordination happens by talking. The tool is a shared memory. At twenty, nobody has the whole picture and the tool becomes the mechanism by which work is visible. At a hundred, the tool is infrastructure — it has to survive people leaving, conventions drifting, and several teams wanting incompatible things from it.

Five people: optimise for nothing to maintain

At this size the failure mode is not choosing badly. It is spending time administering a tool instead of doing the work, and the tools most likely to cause that are the ones with the most structure available.

Cost also behaves differently than people expect here, because free tiers cap on seats. Trello is free for up to ten collaborators per Workspace, which covers a five-person team indefinitely — subject to a ten-board-per-Workspace limit that a habit of one board per client will exhaust faster than you would think. Asana's free plan permits two collaborators, so a five-person team pays from the start: $10.99 per user per month annually, or $54.95 a month for five. monday.com's free plan also caps at two seats, and its paid plans require a three-seat minimum.

Notion is worth mentioning as the specific exception: its free plan is genuinely unlimited for a single user, with the block limit only applying once a workspace has multiple members. That makes it excellent for one person and no more generous than the rest for a team of five.

The recommendation at this size is boring on purpose: pick the one with the least structure that still holds your work, and revisit in a year. You do not yet have the problem the expensive tiers solve.

Twenty people: the visibility problem arrives

Somewhere between ten and twenty-five people, a specific thing breaks: nobody can answer "what is everyone working on and is any of it late" without asking. That question is what the paid tiers are actually for.

This is where board-shaped tools start to strain. A board answers "what stage is this in" extremely well and "what is Marta working on across four projects" poorly. You can approximate the second with Trello Premium's views at $10 per user per month annually, and you are approximating something Asana treats as its base case — Timeline, reporting dashboards and custom fields, which are excluded from its free plan and included from Starter at $10.99.

The honest framing at twenty people is that you are choosing what to enforce. Asana Advanced at $24.99 per user per month annually — $5,997.60 a year for twenty — buys portfolios and goals, which are only worth that if someone maintains them. An unmaintained Asana workspace at twenty people is more expensive and less useful than a maintained Trello board.

So the question to answer before comparing features is: who owns keeping this accurate, and is that in their job description? If the answer is nobody, buy less tool.

A hundred people: it has to survive people

At this size the tool is infrastructure, and the criteria change again. What matters is what happens when the person who designed the workspace leaves, when two teams want incompatible conventions, and when someone has to answer a question about work that happened eighteen months ago.

Per-seat cost stops being a rounding error: a hundred seats of Asana Advanced at $24.99 annually is $29,988 a year, and Trello Enterprise at $17.50 is $21,000. At those numbers a procurement conversation happens, and the things that decide it are usually permissions, audit, SSO and admin controls rather than views.

The consideration I would weight most heavily, and the one comparison pages consistently miss: how much of your process is encoded in conventions rather than in fields. A convention — a list called "Blocked", a label colour everyone knows means urgent — is invisible to an export and unenforceable on a new hire. At a hundred people, conventions do not survive. Anything that matters has to be a field, a required value or an automation, which is an argument for the more structured tool even though it is the more annoying one.

The migration you should plan for

Most teams change project tools at least once, usually around the twenty-person transition, and the move is worse than expected for a consistent reason.

Exports carry the data and lose the meaning. Trello exports boards as JSON and Asana imports CSV, so cards, titles, assignees and due dates survive. What does not survive is everything encoded by convention rather than structure — which, at a small company, is most of how the system actually worked.

Two practical consequences. First, if you can see the transition coming, make it early: the cost of migrating scales with history, so the cheapest moment is always now. Second, whichever tool you are on, write down in plain language what each board or project is for and what the conventions mean. That document survives migrations, survives departures, and is the single highest-return thing you can maintain alongside the tool itself.

If you only take four things

  • At five: pick the least structure that holds your work. Trello free covers 10 collaborators; Asana and monday.com free stop at 2.
  • At twenty: you are buying enforcement of visibility. Only buy it if someone owns keeping it accurate.
  • At a hundred: anything that matters must be a field rather than a convention, because conventions do not survive turnover.
  • Exports preserve data and lose meaning. Document what your conventions mean — that is what survives a migration.

What this piece does not establish

  • Pricing was read from Trello, Asana, monday.com and Notion's own pages on 6–7 August 2026 and is quoted as displayed. monday.com localises pricing and returned non-USD figures to this reader, so its per-seat rate is not quoted here.
  • The team-size thresholds are a framing device, not a measured finding. Teams differ; treat 5/20/100 as illustrative.
  • I have not run these tools at 100-person scale. The section on that size argues from how the products are structured, not from operating them.

Sources

Who wrote this

Rodrigo KrohlingBuilds and runs SaaS Compare solo Reviewed 7 Aug 2026 I build and run SaaS Compare on my own — the data model, the pipeline, the front end, the deployment and the writing. That is also why it exists: operating a small product solo makes me the buyer this software is pitched at, and I kept finding that comparison sites answered a different question than the one I actually had. I have not run most of the products listed here in production, and no page claims otherwise — what I can offer is that every figure is either traced to a source with a date or visibly marked as unverified.

How figures on this site are sourced and labelled is set out in the methodology. If something here is wrong, send a correction.

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