I think with how current economics work it could also be useful to fine all shareholders when a company commits a crime. Ideally fines in percentage of the current stock value, and perhaps even in two parts, half applied immediately to affect all current shareholders, and the other half applied a week or so later to maximise panic-selling and make the stocks undesirable to force stock prices to make a nosedive.

It’s often mostly shareholders that actively push for enshittification, and they often don’t feel any of the financial consequences of fines on companies as long as the line still goes up. So if you fine in a way that shareholders are negatively affected and stock prices (which is what holds most of the wealth of many shareholders) to plummet then I think that’d be much more effective.

Though jailing CEOs for crimes of their company would still be effective for private companies (though they seem to participate a lot less in enshittification as they focus on long-term strategies instead of maximising quarterly growth above all else). For public companies a CEO is often mostly just a scapegoat for the decisions made by the board of directors and shareholders.