If you’re into the inside baseball of pricing strategy, product packaging, and monetization — and this newsletter leaves you wanting more — we’ve got something for you.

We’re now accepting new members into The Uplift, our private Slack community for SaaS professionals. After a successful trial run, we’re opening the doors a bit wider. Here’s what you get.

If you work in SaaS and want to level up your monetization game, send us your info via this form.

Some people love a surprise party. Others won’t step into a new restaurant without scanning Yelp for an hour.

But one thing’s universal: no one likes an unpleasant surprise — especially when it costs them money.

Cursor’s recent pricing change managed to commit multiple cardinal sins of customer communication in a single move.

Cursor advertised “unlimited usage,” but key models were capped — and that caveat wasn’t clearly communicated.

Users say they got no notice. Usage limits dropped immediately. Customers unknowingly burned through credits and racked up unexpected charges. Refund requests flooded in.

The backlash was swift. Cursor became the subject of a Reddit thread titled “The Great Unsubscription,” where users gleefully posted their cancellation receipts.
Eventually, the CEO had to step in with an apology.

Cursor will recover — and if you ever stumble, you can too. But if you’re planning pricing or packaging changes, remember this:

We’ve all felt the pressure of a cheaper competitor nipping at our heels. Their product might be less capable, but when the price gap is wide enough, some prospects will jump — no matter how strong your feature set is.

This kind of market pressure can paralyze your pricing strategy. Every decision gets weighed down by fear of triggering churn or opening the door to disruption.

Here’s how we helped a vertical SaaS company serving SMBs in the service industry respond with clarity — not panic.

The first move is separating what’s truly differentiated from what’s just table stakes.

In this case, scheduling and attendance tracking were standard — every competitor did it well. There was no pricing power there.

But features like advanced analytics and SMS messaging workflows were unique, especially valuable to larger service businesses managing teams. That’s where the pricing leverage lived.

Most competitors target your entry-level plans first — they’re cheaper to replicate and appeal to more customers. But those small customers are also the least sticky and most price-sensitive.

Instead, we held prices steady on the entry plan and focused increases on premium tiers, where customers:

Founders often fear that lower-cost competitors will undercut forever. But that rarely happens.

In practice, once a competitor starts reaching feature parity, they’re under pressure to show revenue growth — especially in this environment. And the fastest lever for SaaS revenue? Raising prices.

That’s exactly what happened here: over time, the cheaper competitor started following suit with their own increases. The pricing gap shrank — without a race to the bottom.

Keep an eye on competitors — but don’t just copy them.

Your pricing should reflect your strengths, your audience, and where you win. The moment you start letting fear set the strategy, you’ve already given up leverage.

AI-native companies like OpenAI, Cursor, and Lovable are growing at historically fast rates. Each new unicorn seems to bend the growth curve further — and faster.

But let’s be honest: most of us didn’t start an AI rocketship last year.
We’re adding AI functionality to existing products — not building from scratch.
That may feel less flashy, but there are real lessons to borrow from this new breed of software company.

For the past 15 years, SaaS companies slowly warmed up to freemium and free trials.
AI-native companies have kicked the door down.

No credit card.
No forced sign-up.
No “Talk to Sales.”
No KYC delay.

Take Lovable — the first thing you see on their homepage is not a pricing table or a sign-up form. It’s a creation box. You can start using the product instantly.

The goal is to create a fan. Worry about conversion later.

Today’s users have:

If your onboarding flow still requires hand-holding, redesign it.
If it’s already smooth, ask: What can we give away for free to hook interest?

Because the companies that get product in hand faster — and with less friction — are going to win. Not just in AI. In nearly every category.

Free isn’t just a pricing tactic anymore — it’s a distribution strategy.

The best AI-native companies don’t sell features.
They build habits, then monetize usage.

Your competitor’s fancy new feature probably isn’t what’s eating into your pipeline.
It’s their frictionless onboarding, smart prompts, and better time-to-value.

Even Oracle — yes, Oracle — lets you download their Enterprise Edition for free.
The pressure to ungate isn’t limited to SMB SaaS.

In this next era of software, the companies that delay monetization to accelerate adoption will have the leverage later.

🎧 a16z Podcast – "AI Is Upending SaaS Pricing"
Metronome CEO Scott Woody and a16z GP Martin Casado explain why AI shifts pricing from user-based to output-based. Perfect for execs reframing their monetization model around AI capabilities.

🎧 Impact Pricing – “Why Private Equity Firms Are Building Pricing Functions” Host Mark Stiving talks with pricing recruiter Jon Jennings and pricing leader Ryan Walter about how PE firms use pricing transformations to unlock portfolio value.

“The best price is the one the customer is happy to pay, and you’re proud to charge.”
– Marcos Rivera, CEO of Pricing I/O

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