Pros
First and foremost, the work is meaningful. The mission is to "change communications forever", and unlike so many cliched mission statements, we've actually got a shot at making that happen. Businesses have launched based on the existence of programmable SMS. Women have been rescued out of sex-trafficking because they were able to text a shortcode for help. Folks living in poverty have have found public assistance that they wouldn't have otherwise discovered for lack of adequate internet access. But if you're into building photo-sharing apps, you can do that too with MMS. Working for a communications company allows you to impact nearly every sector of the economy. Something like 95% of Americans interacted with a Twilio phone number last year. And because the use-cases are so broad, we're constantly learning new ways that customers use our stuff (compare that to, say, an analytics company where there's more or less a singular purpose for your product). The customers and use-cases never get old. It's good to feel that the work you do matters. The people are great. I came from a small 30 person company where I had spent six years and I just assumed I'd never find that kind of kinship with a group of coworkers before. I'm remote, so my relationships are a bit different than most (more on that later), but every time I come back to HQ there are tons of hugs and smiles. Our engineering team is truly world class. Our facilities team executes at a level of excellence. The people here are genuinely kind, empathetic folks who care enough about their work to do it extremely well. The company cares deeply about its people. Think this is evident if you chat with anyone from the E-Team face-to-face. The salary is competitive and the benefits are generous. The parental leave policy (4 months maternity, 3 months paternity) is industry leading. Un-tracked PTO is legit (though, I agree that calling it "unlimited" is a bit shennanigansy). I've taken up to six weeks off a year. At an all-hands last year Jeff (CEO) said, "I just got back from two-weeks vacation. I say that not to brag but to tell you all to take vacation. We're playing the long game here." Last year we implemented mandatory vacation -- you have to take at least 5 continuous days off. The company and leadership try hard to be on the right side of social issues. The E-Team has gone to great lengths to diversify the workplace. For instance: having women's leadership panels during all-hands, bringing in outside consultants to evaluate our workforce diversity and to reveal unconscious bias in the hiring process, encouraging the employee-led Skittles group, throwing a celebration with hundreds of cupcakes on the day marriage equality passed. Twilio.org was given a huge endowment (don't know if that's quite the right word but I'll use it) to affect social change. We supported efforts to call senators and congressmen to fight for net-neutrality and against internet surveillance. We publish a quarterly transparency report. We publicly sided with Apple in their latest battle with the FBI. Jeff is an incredible leader. He is a battle-hardened visionary, an engaging public speaker and is capable of setting the mission and inspiring the troops. He's also a developer. Don't think the importance of that can be overstated for a company that builds tools for developers. Roy (COO) seems perfectly suited for his job as a nuts-and-bolts counterbalance to Jeff's role as visionary. More importantly, they are good men. This provides great assurance when issues come up that make you say, "I'm not so sure about this..." That's not to say that mistakes aren't made or that the working environment is perfect or that there aren't weeks when we have to sacrifice quality of life for the sake of getting the work done. But it's so much easier to endure those issues when you can trust the character of the leaders and the mission of the work.
Cons
You're going to work hard. There are often 50 hour weeks. Sometimes more. Tasks and job responsibilities aren't always clear. One of Twilio's core values is to "Draw the Owl" -- that is to say that there is no instruction book for many of the things we're trying to do. I put this in the "cons" because, while some people really dig this kind of environment, it's probably also the most common reason why folks quit. If you're looking for rigidly-defined roles and a 9 to 5 schedule, this won't be a good gig for you. Twilio's trying to brave new territory. There's no map. Sometimes we go the wrong direction and have to backtrack. Sometimes the trail is super bumpy. Sometimes the wagon tips over while fording a river. Sometimes people catch dysentery. It's the nature of going places no one has ever gone before and trying to get there before everyone else. Again, it's reassuring that the folks leading the expedition know (roughly) what they're doing and actually care about the people making the trip. But the ride's not always comfortable. If you're looking for things to complain about, you'll always find them. Similarly, the road to career growth isn't always apparent. I imagine that this in part stems from not knowing what roles we'll need two years down the line. I can name dozens of people promoted over the last few years, but I doubt many of them had that job in mind 12 months prior. In many cases, that job didn't even exist. Based on what I've seen, if you work hard and handle your workload, you'll gradually get more put on your plate. That "more" often evolves into a new position with a new title and new salary. The remote experience isn't awesome. 75% of the company is colocated in SF so, naturally, a lot of the culture revolves around HQ. There are impromptu celebrations, social activities and hallway conversations that you'll miss out on if you're not at HQ. It's easy to feel like an outsider. It's a known problem that folks are actively trying to solve. We recently switched to a new video conference provider, have experimented with leading all-hands from remote locations, and surveys have gone out to ask remotes how we can improve. Company wide adoption of Slack last year helped a lot too. All that said, collecting an SF salary while not living in SF is pretty cool. If you live in the States and want to work in engineering, you'll have to work out of either the SF or Mountain View offices. It's a bit disappointing that we haven't figured out how to utilize a remote engineering team, but that does seem to be the norm. It does seem that we're improving as we now have engineering offices in Estonia and Bogota. But for the most part, if you're a developer, you must be willing to relocate to SF. We've outgrown HQ. WiFi there is pretty bad. This is frustrating for remotes too as video conferences hang and drop. There aren't enough conference rooms and telephone booths, so there's often a lot of background noise on calls. These issues should be resolved when our new HQ opens. I haven't heard an official ETA yet, but I'm guessing early 2017 at the latest. There seems to be a "if you want to get something done, set a meeting" culture at HQ and the open workplace is fairly distracting. I've certainly found it easier to put my head down and work while being remote. Twilio's certainly not a perfect place, but I think it's easy to get a warped perspective of what constitutes a "normal" work environment when you work in tech. My guess is that if you took the average non-tech worker (or the average office worker from a generation ago) and dropped them into the Twilio office, showed them the benefits, showed them the culture, the free lunches, the stocked kitchen, the Wednesday night dinners, the track jacket ceremony and the $30/month Kindle reimbursement, they'd be astonished that workplaces like this exist. It's worth tossing a disclaimer in there that I'm a remote employee working on one of the few fully-remote teams, and am largely shielded from the day-to-day BS that pops up at a company of Twilio's size. My experience is quite different than that of most Twilions. Take my review with a grain of salt.
