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Pricing projects usually start the same way.
Good intentions. An urgent need to change. A desire to unearth the skeletons. A push to future-proof the model against shifts in technology and AI.

But they don’t end the same way.

After six years of leading pricing changes for companies ranging from $5M to $300M in revenue, I’ve learned there’s no obvious segment or category pattern that explains why some companies successfully roll out a new pricing model while others end up right back where they started.

Instead, there are two forces that quietly kill pricing projects across every market and software category.

The research takes five months.
Executives need another three months to align.
A sales kickoff or product release pauses everything for three more.

Suddenly, a year has passed since the initial decision to change pricing. The market has shifted. New competitors have emerged. Internal priorities have changed. The team feels the need to reopen research and loop in new stakeholders.

That “future-prooff” pricing model turns into a SharePoint file collecting dust.

I once worked with a $110M software company serving nonprofits. We evolved their pricing from a one-size-fits-all model to packages based on feature inclusion. Everyone liked it. But new priorities kept popping up. They stared at the model for too long. Then they acquired another product and had to start over from scratch.

Time didn’t just slow the project down. It killed it.

The second killer is leadership churn.

The person who owns pricing leaves. Pricing gets shelved during the search. Six months to hire. Three months to ramp. Another three months for the new hire to “review the problem” and do their own research.

A full year disappears.

And it doesn’t have to be the “pricing person.” It could be a product or sales leader with strong influence over pricing decisions.

I worked with a well-known $60M company in the data enrichment space. Midway through the project, they hired a new Head of Product. That leader was deep in a platform redesign and didn’t feel ready to touch pricing. The project stalled.

New leaders want to put their own stamp on things. Or they simply have higher priorities. Pricing changes come with perceived risk, especially around change management and external messaging. New feature launches and customer acquisition feel safer. Those metrics usually go up and to the right. Pricing, in people’s minds, does not.

Many believe, incorrectly, that pricing changes inherently risk losing customers or revenue. So they keep shipping what they have, even when they know it’s suboptimal.

To be fair, pricing isn’t the only initiative that loses momentum when stakeholders change. But it is one that gets left untouched for far too long.

If the person who owns pricing is likely to leave in the next six months, your project is at risk before it starts. In that case, you need a longer-term owner identified upfront.

I’ve seen more pricing projects die from long runways and leadership changes than I care to admit. I’ve also seen plenty succeed by deliberately avoiding these traps.

Here’s how.

Pricing needs a committee, but it also needs a hero.

One person must be ultimately accountable.

I worked with a $50M software company serving the building trades. They assigned full ownership of the pricing overhaul to a single leader. They also made it clear that this person’s promotion six months later depended on successfully rolling out the new pricing.

The result? A strong model delivered on time.

No owner means no pricing change. Committees rarely drive major decisions on their own. Pricing needs a system—and someone responsible for pushing it through.

Pricing only moves when it has air cover.

If the CEO and board treat pricing as a real priority, it gets done. If they treat it as “just research,” indecision cascades through the organization.

Many CEOs avoid pricing because they lack experience with it. They’re builders or people managers by background. Private equity firms, by contrast, tend to understand pricing’s impact and prioritize it accordingly.

Setting priority isn’t enough. CEOs should be lightly involved and informed throughout the process.

I’ve seen companies spend hundreds of hours on pricing work only to have the CEO reject it at the final hour. Bringing decision-makers in early isn’t political-it’s practical. Managing up matters just as much as designing a great model.

Pricing projects without deadlines drift.

Teams “exploring pricing” take twice as long as teams that “need pricing live by sales kickoff.”

Every on-time pricing rollout I’ve been part of had a forcing function: a launch date, a kickoff, a contractual milestone. Something that made delay a failure.

Set a tough but clear deadline. Pricing must be implemented by X date. That single decision removes ambiguity, limits over-analysis, and makes it clear this isn’t optional.

Avoid the quicksand of time. Avoid leadership resets. Do both, and your pricing has a real chance of bearing fruit.

These killers take down even the best-intentioned pricing projects. Ironically, the questions teams worry about most at the start - the pricing metrics, the revenue impact, feature analysis - are solvable.

What’s harder is planning for people, incentives, and momentum. Focus on the ‘how and when does this get over the finish line’ to set your pricing up for success.

ChatGPT Go + Ads Guardrails
OpenAI is making a very clear strategic bet: grow the paid base, fund the free base, protect the premium base.

The new “Go” package is the “habit tier.” At $8 per month, it turns Free users into paying daily users with a simple promise: 10x more messages, file uploads, and image creation, plus longer memory and a larger context window.

Open AI also introduced their new ads strategy. Ads are the “subsidy tier.” Ads are being tested on Free and Go to monetize scale without forcing everyone into subscriptions.

Premium stays clean. OpenAI is explicitly using trust as packaging: ads do not influence answers, they do not sell conversation data to advertisers, users can turn off personalization and clear ad data, and Plus, Pro, Business, Enterprise, and Edu remain ad-free.

Open AI’s 10,000-foot pricing strategy:

Recurly’s State of Subscriptions 2026
Retention is no longer a “save churn” motion. It is a growth lever. Recurly analyzed 2,200+ businesses and 76M subscribers and surfaced a clear pattern. The best companies build a reversible customer journey, not a cancel cliff. The 3 stats we wanted to highlight from the report:

Key takeaway: Ship one soft exit and define specific nurture campaigns to bring back hibernating users focused on their usage patterns. Anything reversible beats losing the customer.

WTF Is a Credit? The Hidden AI Tax.
Tropic nails the buyer reality: CFOs are not anti-usage. They are anti-ambiguity. They flag AI renewal uplifts often landing 20–37%, and explain why credit models create budgeting friction when the unit is unclear. Here are 5 questions buyers want answered:

Key takeaway: Credits can protect margins, but confusing credits trigger loss of trust (eventual churn).

Action to consider: Turn the 5 questions into a two-sided tool As a vendor, publish a one-page “credit truth sheet”. As a buyer, demand the same from your vendors and add caps, alerts, and price locks so spend is intentional, not accidental.

AI Pricing Podcast (Flexprice) featuring Marcos Rivera: Why Your AI Pricing Is Failing and How to Fix It

Takeaway: Marcos argues most AI pricing fails because the value unit is fuzzy. The winning path is hybrid by default: keep a predictable base, add usage with a clear unit, and only use credits when you can define exactly what consumes them and how customers can forecast spend.

UsageMoments: Credits, Margins, and the End of Set-and-Forget SaaS Pricing featuring Rob Litterst

Takeaway: A solid breakdown of what changed in SaaS pricing this year. Credits and usage models are becoming the default, AI is pressuring margins, and pricing is now a day-one decision, not a yearly refresh. They also share how teams are testing add-ons and usage guardrails to monetize AI without breaking trust.

“Most companies don’t have a pricing problem, they have a decision problem”

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