Why we named our pricing tiers after sales roles

We argued about the pricing page longer than is respectable.

The easy version was the SaaS default: Free, Pro, Enterprise, each a longer checklist. That page would have been honest about features and dishonest about what Sailsy is.

You are not buying seats of software

A founder on Sales Assistant is not "on the free tier." They are hiring a junior who keeps the CRM from rotting and answers questions about the book. Ten AI chats a month is a constraint on purpose. It is an assistant, not a manager pretending to be free.

Sales Manager is the role most of our users actually need: someone who shows up every day, works the pipeline, drafts the follow-up, and says which deal is leaking. That is why it is a paid plan. You are paying for work, not for a purple badge that says Pro.

Head of Sales is for the moment the founder is no longer the only closer — coaching signals, forecast roll-up, permissions. We will not pretend a five-person team needs that on day one.

Feature grids hide the decision

If we listed "AI" on every column, the page would look competitive and mean nothing. Every CRM has an AI now. The question is whether it behaves like a role you would actually hire.

That is also why the free plan is a real CRM, not a demo with the save button removed. An assistant who cannot see the pipeline is theatre.

The test we use internally

If a line on the pricing page could be swapped onto HubSpot without anyone noticing, we cut it. The names have to survive that test. So far they have.