The month I cut my pricing from four plans to two at $37K MRR: a repackaging diary (2026)

I wrote that line in my own notes on a grey Tuesday in 2026, sitting at $37,000 MRR, looking at a pricing page I had spent two years quietly making worse.

It had four plans. Starter, Pro, Business, Enterprise. It looked serious. It looked like a real company. And it was costing me sales I never saw leave.

This is the diary of the month I deleted half of it.

How I ended up with four plans

No one designs a four-tier pricing page on purpose. You grow into it.

I launched with one plan. Then a few bigger customers asked for seats and SSO, so I added a top tier. Then a wave of tiny users said the entry plan was too expensive, so I added a cheaper one underneath. Then a competitor shipped a mid plan, so I added a "Business" tier to match them.

Every single addition felt reasonable in the moment. Each one solved a real conversation I was having that week. The problem is that pricing is not built one conversation at a time. It is read all at once, by a stranger, in about eight seconds, on their phone.

By the time I hit $37K MRR, my pricing page had four columns, nineteen feature rows, and two different "most popular" badges I had forgotten to remove. I was proud of it. It was quietly strangling my funnel.

The number that made me look

The thing that finally made me open the analytics was not a complaint. It was a distribution.

I pulled twelve months of new subscriptions and sorted by plan. Starter and Enterprise were healthy. The top and the bottom did their jobs. But the Business plan, my supposed profit-center middle tier, accounted for just 6% of new paid signups. Almost nobody chose it. It was not a product. It was a wall people bounced off on the way to a decision.

Worse, my support inbox told the real story. I counted the "which plan should I get?" emails from the previous ninety days. There were forty-one of them. Forty-one people who wanted to pay me and stopped to ask permission first. Every one of those was a person I had confused into a delay, and delay is where trials go to die.

What the research actually says (and where I ignored it)

Before I touched anything, I did something I should have done years earlier. I read what people who study this for a living had found, instead of trusting my gut.

The consensus is blunt. One widely cited breakdown of pricing-tier data (SaaStock, 2024) collects the numbers: companies with three tiers showed meaningfully higher average revenue per user than those with four or more, one experiment moving from four tiers to three lifted conversion by around 27%, and Intercom's consolidation from six plans down to three produced a roughly 17% jump in conversions on its own. Baremetrics' pricing guide puts the mechanism plainly: past about four tiers you trigger decision fatigue that stalls people right on the pricing page (Baremetrics tiered-pricing guide).

The reason is human, not financial. More options do not feel generous to a buyer. They feel like homework. Three named effects were all working against me at once: the decoy effect (a middle option exists mostly to flatter a higher one), the compromise effect (people flee the extremes and cluster in the middle), and plain choice paralysis (too many columns, so the easiest decision becomes no decision at all).

Here is where I broke with the textbook. The research points at three tiers as the sweet spot. I went to two.

I did that because my product did not actually have three jobs. It had two. There was a person using it alone, and there was a team using it together. The "Business" tier had only ever existed to look like a middle. It described a customer who did not exist. Forcing a third plan into a two-shaped product is how you end up with a decoy you have to maintain forever.

The redesign

Here is what changed, in plain terms.

I collapsed Starter and Pro into a single Solo plan and set it at $19, above the old Starter and below the old Pro. I killed Business entirely. I turned Enterprise from a priced column into a quiet "Talk to us" link at the bottom, because the handful of people who need it were always going to email me anyway, and pricing it publicly only scared off the self-serve buyers standing next to it.

Nineteen feature rows became seven. The two "most popular" badges became zero, because with two honest plans you do not need to tell people which one is popular. They can see it.

I grandfathered every existing customer at their current price and told them so, in a short email with no marketing in it. That email is the reason the next part did not go worse.

What happened to the numbers

I will be honest about the shape of this, because the first week looked scary.

Trial-to-paid conversion in the first ten days actually dipped. My guess is that a redesigned pricing page confuses your warm, mid-funnel traffic for a moment. People who had half-memorized the old layout came back and had to re-orient. If I had panicked and reverted on day four, I would have "proven" that simplifying hurt.

By the end of the month the picture was clear and it was good. New trial-to-paid conversion rose from about 3.1% to 4.4%. The "which plan should I get?" emails did not shrink, they nearly vanished: five in the following thirty days, down from forty-one. And the quiet win I did not expect: average new-customer revenue went up, not down, because the old Starter buyers who used to anchor at $9 now started at $19, and a chunk of former Pro-curious users moved onto Team.

MRR went from $37K to a little over $40K inside two months, and almost none of that came from new traffic. It came from the same visitors making a decision instead of closing the tab.

The one thing I would tell past me

If you take one thing from this, take this: count how many of your paying customers actually live in each plan before you add another one.

A pricing tier is not free. Every column you add is a column every future visitor has to read, compare, and rule out before they can give you money. A plan that only 6% of people choose is not serving 6% of your customers. It is taxing 100% of them for the privilege of being ignored. Delete it, and watch what the survivors do.

Keep reading

• The month I killed my free plan at $16K MRR
• Raising prices on existing customers: my $18K MRR diary