Pricing Roundup: AI Pricing is Everywhere

Plus: Introducing Private Questions 💬

Jul 25, 2025

Welcome back to Good Better Best!

If you missed it this week, we launched a new feature in PricingSaaS called Private Questions. Here’s how it works:

You submit a question directly from your PricingSaaS dashboard
We route it to an expert in the PricingSaaS network
You get a thoughtful, direct answer from the right person

If you’ve been sitting on a meaty pricing question, now’s your chance to let it rip! Ask your first question today.

🚨 Reminder: This is the last week to apply for a free Pricing Power Assessment from Ulrik and the team at Willingness to Pay. The assessment combines deep financial analysis with qualitative interviews to identify if you have pricing potential, quantify how much, and how to take advantage. Click the image below to apply 👇🏼

Why your billing system might be killing your product velocity

Usage-based pricing is transforming product management from the ground up. In a recent podcast episode, HubSpot's Brandon Walsh explained why billing must be designed with the same rigor as onboarding flows, how every team becomes customer success in usage models, and why product managers need cross-functional fluency to succeed in this new paradigm. Get the key takeaways and insights in this recap.

Read the Post

The Last Month in AI Pricing

It’s been a while since I’ve done a roundup and the last month has provided plenty of material. Sharing notes on three of my favorite observations below.

1️⃣ Cursor’s Pricing Backlash

The most overlooked skill in SaaS pricing isn’t complex modeling or competitive analysis, it’s communication. And last month, Cursor found out the hard way:

If you missed it, Cursor adjusted the pricing model for Cursor Pro, shifting to a monthly credit pool to manage costs for frontier models.

Some customers complained that they ran out of usage quickly, while others complained that they were unknowingly charged for additional usage.

However you spin it, it’s clear the change wasn’t communicated clearly.

It’s proof that even if the new model is better for the customer, with poor communication, they still won’t get it.

Visuals and real-life examples help. It’s one reason I’m such a fan of how Clay handled their pricing change last year:

Clay shared a real customer example to highlight the need for credit top ups.

This level of clarity isn’t optional anymore. It’s table stakes for modern SaaS pricing. You literally cannot over-communicate when it comes to pricing changes.

2️⃣ Google Got Me

Last week, I got hit with a Google Workspace upgrade. If you missed the announcement earlier this year, here’s the TLDR:

Previously, Google offered Gemini as a $20/mo add-on (similar to ChatGPT and Claude). In the new model, they bundled Gemini into the existing tiers for an additional $2/mo.

In practice, here’s how it works:

Before: Business Standard ($12/month) + Optional Gemini ($20/month) = $32/mo
After: Business Standard with Gemini included = $14/mo

While the equation above makes it look like a steal, the approach is facing backlash because it takes the control out of the customers hands.

This week, Brian Morrissey captured the sentiment perfectly on his podcast, People vs Algorithms. His point:

“If the product is so good, why do you have to force it on me?”

It’s a fair criticism. But I’d argue Google kinda had to do this.

Gemini was late to the party, and had to find a way into the game with ChatGPT and Claude. Offering Gemini for the same price would force many customers to make a choice between the two.

Bundling Gemini into GWS allows customers to use it instead of or in addition to ChatGPT and Claude. Its a smart approach for an incumbent that has the cash and user base to subsidize AI adoption in ways OpenAI and Claude simply cannot.

3️⃣ OpenAI’s Pricing Role

Ismail Madni had a LinkedIn post this week that elicited entertaining replies from the B2B SaaS pricing community:

Some of my favorites:

Dan Balcauski + Chris Herbert 💯

Andrew Yee 😂

Mihir Wagle 🎯

I’ll leave it there for the day. Hope you all have a great weekend!

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