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Alan Wizemann — Articles

Insights and expertise on digital transformation, AI adoption, product strategy, and technology leadership.

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Nobody Majors in Transformation

There is no degree for this work, no major you can declare, and the people who are good at it almost always backed into it sideways the way I did.

The Transformation Succeeded. The Industry Didn't.

The hardest builds of my career did exactly what they were supposed to do, and were still undone by forces nobody in the building could touch.

When It's Actually Their Money

I've now worked inside nearly every funding model there is. The private, family-owned one changed how I think about time, discipline, and what a long-term decision actually feels like.

Consultants Can Map a Transformation. They Can't Make It Stick.

A plan is something you can rent; a capability is something you have to build, and the difference is everything.

Real Time Is Table Stakes

For years the goal was to see the business as it is right now. We got there, and then realized 'right now' is already the floor. The advantage is in what you can see before it happens.

Measured to Fail

The number everyone quotes about transformations failing says more about how we measure the work than about whether the work ever actually worked.

Start With the Org Chart

The org chart isn't just how a company is organized; it's where both the opportunity and the resistance quietly live, and reading it is the first move I make.

The Definition of Done

AI made shipping things that look finished nearly free. So 'looks done' and 'is done' have come unbundled. The definition of done is what closes the gap.

Could One Person and AI Build the Whole Thing?

Rainfall cleared the App Store, but the launch was never the thing I was testing. The real question was whether one person and AI could build the whole stack.

The Red Flags That Are Actually Green Flags

I almost built an AI hiring filter myself, then walked away. Now I'm the candidate it screens out, and the best hires are the ones it quietly makes disappear.

We Almost Built the Wrong Tool for Our Sales Team

The whole company agreed our salespeople needed better materials and better routes. A small team went and found out what they actually needed, and it wasn't either of those.

Don't Boil the Ocean. Find the Case.

When you inherit two dozen disconnected systems, the instinct is to map everything before you touch anything. The faster path is to find the one thing your whole business runs on and start there.

The Distributor Became a Media Company

Sitting in the middle of a network with the first-party data and the inventory, a distributor stops being a company that moves boxes and starts moving markets.

Harnessing AI for Scalable Enterprise Engineering: A New Paradigm

Discover how AI-driven teams enhance collaboration and efficiency. Embrace the future of enterprise engineering today!

The Sunk Cost Problem Nobody Talks About in Tech

The same inflated business case projections that get initiatives funded are what make them impossible to stop. Time to value is the reframe that changes how you prioritize everything.

Why I Stopped Running Projects

Project-led organizations build things that end. The shift to durable product teams changes what gets built, who owns it, and how fast an organization can actually move.

AI Isn't Going to Replace Your Sales Team. Here's What It'll Actually Do.

The fear that AI replaces sales relationships is backwards. Here's what happened when Southern Glazer's built AI tools for their sales team instead of against them.

Tech Is Dumb Out of the Gate

Automation doesn't eliminate the need for the people who know the work. It depends on them. The warehouse worker who trained the system and got promoted is the story most companies miss.

The Power of Pausing: Why Taking Breaks Can Spark Innovative Solutions

Discover how taking breaks can spark innovative solutions. Prioritize your mental well-being for better results. Start your journey to creativity today!

Why I Keep Revenue Goals Out of My Vision

Putting a revenue number in your strategy caps what teams build toward. Here's a different approach, backed by a platform that hit $3.86B without one.