Rob Litterst has spent the better part of a decade trying to convince SaaS founders that the pricing page is the most strategic surface in their entire product. He sharpened that view as a pricing consultant at ProfitWell, led audience growth and monetization at HubSpot’s The Hustle, and now runs PricingSaaS with cofounder John Kotowski. Their platform tracks how SaaS companies actually package, price, and re-price their products.
We sat down with Rob to talk about the pricing experiments quietly driving upgrade rates in 2026, what AI is doing to the SaaS value ladder, why founders are still moving too slowly on monetization, and the under-the-radar trend he believes will define the next 12 to 18 months. Rob also writes the weekly newsletter Good Better Best, which has become required reading for product and growth leaders rethinking how they charge.
About Rob & PricingSaaS
Tell us about PricingSaaS. What’s the mission, who do you serve, and what gap in the market did you see when you started it?
My partner John and I came to PricingSaaS from different backgrounds. I’d been a pricing consultant at ProfitWell, and John had been a Chief Product Officer at multiple startups. Through those experiences, we both realized how critical pricing, packaging, and monetization are to a company’s growth, and how few companies actually know what they’re doing.
I was tackling that from the content side with a newsletter. John was building a database of pricing pages and tracking pricing changes. Our goal has always been to democratize access to pricing expertise, so founders can make smarter pricing and packaging decisions without paying a fortune for a consultant or hiring a full-time pricing manager. There wasn’t a great source of data, thought leadership, or community around pricing, so we built one.
What’s your background, and what led you to focus specifically on SaaS pricing as a content and research vertical?
I’ve been in SaaS for about 13 years across sales, marketing, and consulting. Back in 2018, I fell in love with pricing and packaging while working at ProfitWell. I started writing a newsletter about pricing in 2020 while I was still consulting. It was partly to get better at my job, and partly to give my clients useful resources.
One reason we love this work: the pricing page is where product meets strategy. It’s the single page where you can learn the most about what a company is trying to do, how they value their product, and who they’re going after. There’s a lot of gold to mine if you’re trying to understand a company’s strategy.
PricingSaaS has built a loyal following among founders and product leaders. What’s been the single biggest driver of that audience growth?
Organic, across three channels: daily LinkedIn posts, a weekly newsletter, and quarterly trend reports. That’s our content motion. We’ve started leaning into paid acquisition, but our audience today is roughly 90% organic.
The Core Topic: SaaS Pricing Experiments
You recently wrote about five SaaS pricing experiments driving upgrades. Without spoiling the whole piece, which one has surprised you the most in terms of results, and why?
Playing with billing cycles. We’re in a weird place in SaaS and AI right now where customers hold a lot of power. The tools powering Claude and Lovable have endless willingness to pay, but the rest of the SaaS market is in a fight for its life trying to become indispensable.
Most companies have only ever offered monthly and annual. But quarterly and semi-annual cycles are worth testing if your billing system can support them. Buyers right now don’t want to commit to long-term contracts, and quarterly is a great meeting point: more than a month, less than a year.
What’s the most common pricing mistake you see SaaS founders make in 2026, and what’s the single highest-leverage fix?
It’s psychological. Founders need to realize they have to ship pricing changes faster, as AI evolves, as their costs change, as they add features. Too many companies are stuck in the old mindset where you set pricing and don’t touch it for a couple of years. That’s not going to work in the age of AI.
Usage-based, hybrid, seat-based, outcome-based: the pricing model debate is louder than ever. Where do you actually land in 2026, and is there a default you’d recommend for early-stage SaaS founders?
Outcome-based pricing is a great ideal to strive for, but it’s hard to execute. Most SaaS companies aren’t in a place where outcomes are realistic. Customer support is the exception, which is why we’ve seen so many CS companies shift there.
The most important thing is that whatever you’re charging for makes sense to your customers and feels fair. Customers have a lot of power right now, and they’ll choose the companies that make it easy for them.
If I had to make a sweeping recommendation: hybrid is the name of the game. You want predictable revenue plus a consumption layer for expansion. That’s where most SaaS companies land now, and even the bigger players who historically charged for licenses are shifting more into consumption. Not surprising given what AI is doing to the cost side.
AI features are quietly reshaping how SaaS companies price. What pricing patterns are you seeing emerge around AI-powered functionality, and what should founders be watching for?
When something hits the Claude or ChatGPT pricing page, SaaS companies start building functionality around it within a month. We saw it with deep research, then MCPs, and now agents and skills.
What’s interesting is the natural transition: features from the frontier labs permeate the product layer and often get commoditized. With MCPs, most companies are using them as a distribution and acquisition strategy. They put them in the starter or free tier to get embedded in people’s AI workflows.
Skills are a different story. Companies are packaging skills as differentiators. The more skills you offer, the more sophisticated and higher-volume work you can do. This is the new value ladder in SaaS: faster work, more sophisticated work, higher volumes of work. It’s replacing the traditional features-and-usage ladder.
Industry & Forward View
What pricing trend do you think will define SaaS over the next 12 to 18 months that most founders aren’t paying enough attention to yet?
Charging for execution. More companies will start pricing the actual work-to-be-done into their models. A few already doing it:
- Customer.io, which just launched its AI agent beta
- Day.ai, an AI-native CRM
- Relay, which is essentially Zapier for agents
These companies all have metrics or levers in their pricing tied to execution, meaning the platform doing work on behalf of the customer. This is the path to outcome-based pricing. Most companies won’t get to true outcome-based pricing anytime soon, but if you have an execution layer in your model, you have a credible AI story and a path to get there.
Are there any specific SaaS companies whose pricing pages or monetization strategy you think every founder should study? Why?
HubSpot is canonical. They take pricing seriously, and the company has evolved a lot as they’ve added more hubs.
Clay is a great example of evolving pricing alongside value prop. They recently added a new usage metric called “actions” on top of data credits, which really changes the scope of where they’re going.
Figma just reported earnings, and it went well. They’re seeing solid usage from their AI tools. A lot of investors thought they were dead in the water in the AI shift, and clearly not.
Notion is always worth watching. They’re constantly iterating, and their pattern of launching things as add-ons before eventually integrating them into the product is interesting to track.
Where to Follow Rob’s Work
You can connect with Rob on LinkedIn, subscribe to his weekly newsletter Good Better Best, or sign up for PricingSaaS to access the research engine and resources.
About Rob Litterst
Rob Litterst is the cofounder of PricingSaaS, a pricing research platform tracking how SaaS companies package, price, and re-price their products. He writes the weekly newsletter Good Better Best and has spent more than a decade in SaaS across sales, marketing, and pricing consulting, including stints at ProfitWell and HubSpot’s The Hustle, where he led audience growth and monetization. Rob’s work focuses on democratizing access to pricing expertise so founders can make smarter monetization decisions without hiring a full-time pricing manager.
