So let's break it down >Something we could do better at is making it really possible and a really great experience
First thing: It's not going to be a great experience to be redundant or have the company you've helped build to no longer need you or you're no longer contributing.
> for people to leave when they know that it’s time
What is that even meant to mean? 'they know it's time'? How do they know it's time. Is it time because you've fired them? Is it because they're redundant.
They say they've got great management, but it sounds less like they've got good management, it sounds like they've got management that's been lucky. The company has grown quickly and hired quickly and their options scheme means people are massively incentivized to stay. But if you don't want people to stay why don't you just modify their vesting schedule, or offer them redundancy? Or retrain them? Or move them a different project. The reason you're having a problem getting rid of the people you don't want is because your management team is failing to make the decisions that are best for the company because they prefer feeling popular. This seems like a bizarre thing to brag about.
I think what it comes down to is that I really object to this disingenuous double speak where the company is trying to say "Isn't this great! This is a great thing we're really happy trying to solve this challenge" - when actually it's not a good thing, and it's fairly obvious to anyone with a brain, so it's quite insulting to have someone to lie to your face like that.
My guess would be that they feel (or some employees feel) that they've over-rewarded some early employees who are now motivated to stay at the company largely for the purposes of vesting stock options rather than to engage fully.
That said, there are a whole slew of really tricky things around options and compensation here. What's the comparative stock/option holding granted to executive/C-level staff, and are they under the same scrutiny to measure their performance and output?
Generally I think it's typical for there to be an order of magnitude difference between stock holdings for investors & high-level executives relative to even the first few full-time hires.
To play devil's advocate, it's 'understandable' that if you want to run the fastest, cheapest ship that you would simply want to get an employee in a seat, have them build/ship/market/sell the product for a few years and then have the employee move on if & when their productivity drops.
Continuing that idea (and I'd hope that Monzo nor many other tech startups are culturally this cynical) - it reduces the need for career growth planning, management expertise, and reduces the risk of pesky situations like the employee remembering bad company decisions or gaining too much access or influence within the organization, etc.
There are more successful ways to handle those cases (although they require effort from the company, and their results should be scrutinized by staff), and employers that want to retain knowledge workers will find ways to incentivize them to keep their staff on-board and effective.
There are few better incentives than continued business success (particularly where the employee can engage in force-multiplying their own success via building the company/product) and challenging technical or business problems.
