[movingmove]

I had the "pleasure" working for Twilio for over 4 years. I cannot tell how much this showed me how you can fake it til you make it in SF.

Twilio tried to expand into Europe and failed miserably. Customers (especially German ones) wanted exact locations of data, exact routes of packet transportation, wanted features Twilio promised on Slides but never delivered.

I was part of at least 4 customer meetings (the biggest in Europe) where the clients just called Senior levels in and told them off.

Twilio was great when it just handled voice and text messaging. It never grew substantially, it never delivered features customers were asking for years. Messy code base, hired product owners with no clue what they should actually build.

Jeff was famous for over-promising and under-delivering. 1 year into my Twilio career, it was clear that the company would fail hard. Colleagues and I had bets on when Jeff will be fired or the company sold. Well, the last few months have been telling.

A sad story, since they had a great core product, really smart people, great people working there. But especially through the pandemic, they grew an insane amount without actually building anything of substance.

[ejb999]

this is pretty much my take as well - but as a non-employee - I was a big fan and user of twilio when they first came out, even attended the very first few twiliocon conferences in SF, (mostly developer focused) where they would announce and release new features - lots of excitement as new things got announced and rolled out during the annual conferences.

Then after not very long, you would goto the conferences where they would make announcements about what is coming, but no real timelines attached and some things that were announced, never really materialized - or not fast enough etc.

Then they started diversify like crazy into other areas, unrelated, and I think they really lost their focus - stopped using them (99% stopped) a long time ago for those reasons.

[karim]

One year into it you knew the company was going to fail yet you stayed on for 3 more years? What happened there?

[smt88]

Knowing a company is going to fail doesn't automatically mean the compensation and/or culture don't work for you.

One way a company can be mismanaged is burning money it can't afford on ridiculous employee perks, like when Twitter got its own DJ.

[ctz]

I'm not the OP, but agree with their assessment and stayed 3.5 years despite that. For me, the reason was the vesting schedule: 4 years with a 1 year cliff.

[idopmstuff]

But why would you want to vest a bunch of options/shares that you think will decline substantially in value over your tenure there?

[shawabawa3]

Hypothetical scenario:

You join and are granted 400000 options at $10 strike and stock is worth $10

2 years in and the stock price is now $110

You think the company is terribly run and the stock with crash at this point. However if you quit, you lose the 200000 unvested options worth $2M on paper

Even if the stock crashes to $20 they are worth $200k

Hard to find a better paying job in that situation until the options are fully vested

[kelnos]

I mean, you can take it quarter by quarter. If you get your vest and (even if you sell them immediately) the value is worth it to you, you'll probably stick around for another quarter to get the next one.

You don't just say on day 1, "I don't think the company is going anywhere, but I'm committing to staying another 4 years".

[vineyardmike]

Being an employee isn’t the same as being an investor. Some jobs are good even at bad companies.

[gwbas1c]

I was in a similar situation. A year into a job with a large company, I realized the company had issues and that I didn't like most of the people I worked with.

I stayed for ~1 year after I realized I needed to get out: At the time I was getting paid very well, had very low expenses, and was saving to quit my job and start my own company.

My original plan was to stay a few months longer to build up some more savings, but "things happened" inside the company. I was re-assigned to a horrible manager; I hunted around for another assignment (on the advice of my boss's boss,) but that was going to be Flex-based. (And I bet correctly that Flex was going to fail in the marketplace.) I decided that I was better off quitting and self-teaching myself HTML + Javascript instead of getting paid to learn Flex. However, I could have stayed for a 2-3 more years, worked in Flex, made a boatload of money, and selectively applied for jobs elsewhere.

> One year into it you knew the company was going to fail yet you stayed on for 3 more years?

There's a lot of risk in changing jobs: If you "have a good thing going," it's best to bide your time until a better thing comes along. Interviewing is quite time consuming too, so don't assume that someone can just casually make a few phone calls and walk away with a "better" job. (This is especially the case if you have kids, a house, a mortgage, and a significant other who has their own career.)

[specialist]

Job mobility declines significantly with marriage, kids, and mortgage. I've toughed it out before, mostly to keep the good healthcare benefits. (This was prior to ACA eliminating the preexisting conditions BS. We didn't want the hassle, uncertainty of changing insurance during a pregnancy.)

Also, it's hard to job hunt when you're already over worked, both at home and the office.

Also, the devil you know. Every new job is a gamble. After a while, all the jobs kinda smell the same. So what's the point in playing frogger?

[collingreen]

Part of the problem, perhaps?

[Solvency]

So: What big brain moves did you think Twilio should have made during your 4 year tenure there that they failed to do?

[movingmove]

For starters, actually trying to deliver what they promised? Get the actual hard, boring job done bigger clients wanted. The not-sexy work behind the scenes. Main problem is that it doesn't look good on paper, and Twilio hired an absolute insane amount of people.

My guess is they profited _a lot_ from the crypto hype. Exchanges sprung up right, left and centre and they all needed customer call centres etc. So Twilio grew through that. Saw super high growth and thought: All is well. All the while the "real" customers didn't get the features they needed, and quit Twilio after a 6 month trial period.