wgmatw: The Rise of the IC CPO, Building AI Features, and the Problem with Credit-Based Pricing
What Got My Attention This Week, as a product leader
On the final week of 2025, what got my attention as a product leader were a few videos and posts that seemed to orbit around the same underlying tension — coming from very different angles.
What kind of tension? Speed vs. depth. Tools vs. craft. Experimentation vs. commitment.
Let’s get into it.
1/ Webflow’s CPO on how she AIs
On the most recent episode of ‘How I AI,’ Claire Vo interviewed Webflow’s CPO, Rachel Wolan.
Rachel exemplified the emerging ‘IC CPO’ mindset — sharing how she built her own ‘AI Chief of Staff,’ to manage calendar, email, and event prep, as well as how Webflow runs internal ‘builder days’ to level up AI usage across the company.
What I appreciated most was that while there are plenty of practical workflows, this is not the typical ‘AI does product for you’ hype. The core thread is that being an AI‑native exec means being in the weeds, building personal software, and using it to improve your performance. Sometimes that means getting brutally honest feedback on how you spend your time.
In this new era of ‘IC CPOs,’ it's also important to lead by example. As Rachel puts it,
“I really want my team to level up. It would be inauthentic for me to tell them, ‘Hey, you need to prototype with AI’ if this isn’t something that I’m doing every single day.”
With so many people focused on what AI can generate for them, it’s a good reminder that the hard part of product is still judgment: where you show up, what you delegate, and what you say no to.
2/ Descript’s CEO on building AI features
Aakash Gupta had Descript CEO Laura Burkhauser on the Product Growth podcast this week. The conversation was a good reminder that speed for the sake of speed can quietly flatten ambition. The fastest path is often ‘slap AI’ on your product, but you lose the chance to imagine the product your users actually need.
Descript has been an AI‑native product since inception, and during the AI boom the team kept asking,
‘What do we do now that LLMs are generally available to bring into Descript?’
Laura kept returning to the idea of mapping the user journey first. That discipline let the team solve the right problems, roll out valuable and differentiated features, and design the right interface — sometimes a single button, sometimes a full agent — instead of chasing whatever AI pattern was trendy that week.
Laura also got into her IC-to-CEO progression, evals, and how they measure and quantify success for AI features like tools and Underlord.
3/ Kyle Poyar on pricing agility, and the coming backlash to AI credits
I’ve always appreciated Kyle’s take on all things pricing. In a recent LinkedIn post, he mentioned that while many are predicting 2026 will be the year of credit-based pricing, he thinks it may also be the year of a backlash against credits.
If 2025 was about scaling AI pricing experimentation, 2026 should be about consolidation, predictability, and trust.
Enterprises don’t hate usage-based pricing. They hate surprises. The same is true for vibe coders and solopreneurs — nobody wants unexpected fees, hidden costs, or pricing traps.
Using Salesforce as an example, Kyle points out the many flavors of AI credits: pre-purchase credits, pay-as-you-go, and pre-commitments with no upfront payment.
He also makes the point that seat-based pricing isn’t going away:
“If AI replaces people with digital labor, a seat-based model is a recipe for a declining business… But AI replacing people is still a relatively small phenomenon. Most adoption is still about AI augmenting people.”
This experimentation vs. commitment tension will continue to play out across AI products. One example I can think of is Lovable’s recent tests with ‘top up credits’ — which I suspect will be followed by their competitors, if they haven’t already.
Bonus: Linear CEO Karri Saarinen on design-to-code being a trap
I couldn’t end without pointing to this post by Linear CEO Karri Saarinen, which got lots of attention on LinkedIn.
Karri argues that designing in code too early doesn’t elevate design — it compresses it. When designers become builders ‘too soon,’ they start making conservative bets, optimizing for feasibility instead of vision.
The entire post is a great read, but here are some of the highlights:
“Whenever a designer becomes more of a builder, some idealism and creativity dies. Not because building is bad, but because you start out including constraints earlier in the process than they should.”
“Once you become the architect and the builder, or the designer and the developer, you start making more conservative bets.”
“Designing in code is just a path to local maxima and ruin.”
Great design (and great product thinking) often requires a phase where reality is intentionally suspended. Not ignored forever… just postponed long enough to dream something worth building.
ps.
A good PM friend asked me if I was going to write a post about my predictions for 2026. I told him I wasn’t planning on it — the future seems harder to predict these days.
That said, the tension I mentioned above is one I think will continue in 2026.
As tools get faster, cheaper, and more automagical — and as the FOMO increases — teams will continue to optimize for speed. Lines will blur. That will do wonders for productivity and outputs.
At the same time, winning products will always need strong vision, judgment, and risk-taking. Whether it’s AI in product, code in design, or credits in pricing, the real work keeps moving one layer up.
In 2026, play your role wisely.
Happy New Year.
