Just curious - why is this important? Is it something like given the upcoming IPO, the current investors asked for someone more experienced? but that would be odd considering he was on the tech side and not on business

I read elsewhere they were looking to IPO later this year. Seems like an odd time to jump ship.

That's not unusual at all. A lecture at Harvard Business School about startup IPO mentioned that first time founder CEO and first time board member get more often then not replaced. Read about the business case of Lewis Cirne who got replaced at his first company Wily, and founded later New Relic with many lessons learned.

"Get more often then not replaced" not quite sure what you meant here. Could you say a bit more?

Agreed, especially the statement from the company that they wish him best in future endeavors generally means he is not leaving of his own accord or at best the decision was mutual. There are definitely differences in being an inwardly facing VP, Engineering and an Pre-IPO member of the executive committee. Maybe just wasn't his bag.

What would you expect the wording to be if it was his own decision?

So is Arash Ferdowsi no longer the CTO?

What is his position now?

his position now is just "co-founder". https://www.dropbox.com/about

>That kind of five-year tenure at a startup in Silicon Valley alone is pretty long, to be sure

Does this journalist not even know about 4 year vesting schedule that are common after an acquisition?

It's common, but many people do not stick it for the whole 4 years. In fact, I have seen 12-24 months more often than the full 4. If your acquisition was even a tiny bit high profile, any new job offer will come with a stock grant that more than makes up for what you lose by leaving early. (And in fact, if you are in that position, you should be using it as a leverage when negotiating a new job offer)

It really depends on what you think the EV is. Dropbox has pretty high EV if you're in his role, I bet, which is why people are speculating in the first place. (Does this mean Dropbox is not as valuable as it seems from the outside?)

Personally, knowing how hard people there have worked over the last 6 years, I imagine he just needs a break.

Yes, obviously $100k of Dropbox stock is worth much more than $300k of $randomStartupStock. Although at a VP/C level status, I'm not sure how much of a difference an extra few months (or even a year or two) of vesting makes.

If you have a sizable chunk of equity and the liquidity to exercise options (or if they are already exercised) then leaving the company can make it easier to trade on that equity.

Leaving is also a way to get your money if the stock is not liquid, by negotiating with the new company to compensate for your lost options.

I take it you're referring specifically to (1) lock up periods and (2) the negative signals you send when a CXO liquidates shares while still being a CXO?

In other tumultuous times, the dot com days, there were many examples of people simplifying all the rules about when to trade or what they could trade, by ending their employment. I did not take that route but many did.

I was remarking that when the future has many variables and you want to simplify, that can be sufficient motivation to leave a company.

He joined Dropbox after it became common to have ROFRs and other terms that made secondary sales less possible. I don't know the terms he has, but I'd be surprised if Dropbox stock is being moved the way, say, Twitter or Facebook stock was back in the day.

No, I actually believe at that level, job changes are extremely rare unless they are retiring or find an offer they cannot refuse (a big step up, like CTO of Google, etc.).

There is more to it than just the 4 year vesting schedule. Such as how long the startup gives people to execute options and the amount of taxes owed if you have to execute within 3 months.

I wonder if he will join Uber.

Depends how many files he's downloaded, I guess.