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A media company hired a CPO from Big Tech to go AI-first. His all-hands showcased an AI project. Behind the scenes, one person built it in spare time with no resources.
That is not an AI strategy. That is a press release.
Meanwhile every A/B test result lives in PowerPoint decks on SharePoint. The first real AI win is not agents. It is feeding those decks to Claude and producing a two-page report in 24 hours. One person. No budget.
Find the PowerPoint graveyard.
A client calls them "content affiliates." They are SEM lead-gen operations bidding on the company's own keywords.
I saw this at EverQuote. Affiliates bought our keywords, piped garbage leads, collected a CPL. Progressive pulled out because quality tanked.
Two kinds of affiliates. SEM affiliates sell you back your own customers. SEO affiliates like NerdWallet build trust, creating demand that did not exist.
If your program is mostly SEM, you are paying someone to compete with you.
A strategy only exists when it excludes something.
"We serve enterprise and SMB across North America with a best-in-class experience" is not a strategy. It is a market with adjectives. Any competitor could sign that document.
Most product strategy fails for one reason: it is not actually a choice.
matthewmamet.com/blog/product-strategy/
Solar takes 12 weeks to close. That's a consumer trapped in analysis paralysis with $40K on the line.
The instinct was to optimize the funnel. Wrong problem. Nobody has figured out how to make the buyer feel safe enough to move.
Airbnb had the same issue in 2011. Two-sided fear. They didn't fix it with marketing. They built a money-back guarantee that absorbed risk for both sides.
Build the trust infrastructure first. The conversion follows.
Most product leaders walk in trying to prove they're the smartest in the room. I'm doing the opposite. Rolling over and showing my belly.
At Pearson I needed something from engineering with zero reason to prioritize me. It sat for weeks. Instead of forcing it, I framed my request so it solved their problem too. Then gave them all the credit.
That became the proof point. My requests moved faster because the team decided I was worth prioritizing.
Stop being Mr. Smart Man. Be Mr. Useful Man.
A DTC healthcare startup I advise asked how to fix their culture. I told them to stop trying. The canvas is already painted.
Most leaders waste months reshaping the environment. The org snaps back every time. The better move: bloom where you're planted. Accept the tempo and do your best work inside the constraints.
At TripAdvisor the people who thrived treated the intensity as a feature, not a bug.
You don't have to love the water. Just learn to swim in it.
š” Software is (relatively) easy - it's wrangling PEOPLE that slows the roadmap š¤·āāļø
Donāt blame bugs if launches drag:
- Misalignment stalls delivery, not just code
- Soft culture ā honest conversations
- Clarity beats more process - assign real owners & push for open dialogue š¤
Want velocity? Coach for candor, set expectations. Your people are the true product.
Read more š https://matthewmamet.com/blog/software-is-easy-its-the-people-that-are-hard
š¦ Disruption is easy to spot in hindsight - harder while youāre living it.
š©ļø I saw denial everywhere in the 90s when cloud/web-first tech emerged.
ā”ļø Change always triggers fear, but fatigue or denial hands your edge to hungrier competitors. Donāt half step into big platform shifts: embrace, re-learn - and care more about ux than control panels!
