CWChad Wolpert

Experience

A career built around AI, learning, operations and scale.

Not a CV. A curated professional story—the chapters that shaped how I think and work.

Foundations

University

Computer Science, AI & Image Processing · South Africa + Germany

I studied Computer Science with a focus on AI and digital image processing—before today's generative AI wave made the field mainstream. That grounding in how machines actually represent, process and learn from data gave me an instinct for what these systems can and can't do. I followed that with an MBA in Germany, which pushed me into business operations and strategic thinking.

Computer ScienceAIDigital image processingMBA

Early enterprise AI

IBM Watson

Consulting & Commercialisation · Africa

I worked on IBM Watson in Africa at a time when enterprise AI was genuinely new and genuinely hard to explain. The work was about helping clients understand what cognitive technology could realistically do in practice—separating what was useful from what was just a compelling demo. It shaped how I think about AI adoption: the challenge is almost never the technology, it's the operating conditions around it.

Enterprise AIConsultingCognitive techAfrica

Startup & scale-up

Up Learn

Early Operator · London

Up Learn is an education platform powered by AI and cognitive science—built on the research into how people actually learn. I was an early operator, helping align product, operations and go-to-market as the company scaled. The focus was building repeatable capability: clear ways of working, the right metrics, and teams that could execute as things moved fast. Scaling without losing what made the product special.

EdTechEarly-stageOperationsProductGrowth

Scale-up operations

Morressier

Head of Strategy & Operations · Berlin

At Morressier I led strategy and operations—connecting big-picture direction to day-to-day execution. That meant scaling systems, designing operating rhythms, building GTM infrastructure and driving execution across the organisation. We clarified priorities, redesigned ways of working and built the operating rhythm that let the team move faster with more confidence. Strategy needs a spine.

StrategyOperationsGTMScalingBerlin

Enterprise transformation

LinkedIn Learning

Strategic Accounts & Workforce Transformation · Global

Through LinkedIn Learning I worked with global organisations on enterprise learning, workforce transformation, capability building and AI adoption. The organisations making real progress weren't the ones with the biggest budgets—they were the ones treating capability as a strategic priority, not a training exercise. Real change sticks when people have the skills and confidence to work in new ways.

Enterprise learningWorkforce transformationAI adoptionGlobal

What this taught me

The through-line across twenty years of work in AI, operations and learning.

Strategy needs execution

A brilliant strategy that doesn't connect to how work gets done is just a document. The gap between strategy and execution is where most organisations lose.

Capability drives adoption

Technology and strategy go nowhere without the people capability to back them up. Building skills and confidence is the mechanism, not the outcome.

Scale needs mechanisms

Scaling needs systems, rhythms and clear ways of working—not just more people or more effort. Repeatable operating capability is what makes growth sustainable.

AI adoption is human and operational

AI doesn't fail because the model isn't good enough. It fails because the operating conditions, incentives and capabilities aren't in place. That's where the work is.

See the full CV on LinkedIn

Full work history, recommendations and endorsements.

View on LinkedIn

Let's do interesting work together.

If you're working on AI adoption, operating model change, learning strategy or a messy problem that needs turning into something practical, I'd be happy to talk.