Twilio CEO Jeff Lawson on shifting a 3,000-person company to fully remote

'It's not without its hiccups, but it has worked pretty well'

What’s it like to take a company with 3,000 employees distributed across 25 offices and make it fully remote with just a few weeks’ notice?

I hopped on a call with Twilio CEO Jeff Lawson to hear about how their transition has gone so far, and what he’s learned from the process.

Twilio CEO Jeff Lawson

Remote work isn’t brand-new for Twilio; as with a lot of software companies, many employees have worked remotely. But it’s still a massive shift: Prior to the coronavirus outbreak, Lawson says around 10% of the company worked remotely. Today, it’s everyone.

“For a company like us to go from partially virtual to fully virtual in a short period of time,” he says, “it’s not without its hiccups, but it has worked pretty well.”

Things are weird for everyone right now, so compassion is key

Shifting to remote work might make things feel different for a while — but those differences pale in comparison to the other changes people are coping with in the shadow of the COVID-19 pandemic.

“I think the fact that you are distributed is lesser than the fact that you’re like, not allowed to go outside,” says Lawson. “You’re worried about friends and family and you’re reading the news… those things are more impactful.”

I’ve been hearing the same thing from teams that have been working fully remote for years: Even for people who are very used to this workflow, it can be hard to get work done right now. And if you’re having a hard time with all of this? You’re not alone.

“People who have kids, they’re struggling with how to juggle your kids and still do work and be productive while feeling like you’re giving your kids an education from home.” Jeff tells me. “For people who are single and live alone, you’re not battling with your kids, you’re battling loneliness. For people who are extroverts, you are battling with a lot less human interaction. Or people who are introverts, and are stuck at home with roommates or family and who need space to decompress — they’re struggling with that. Every single person is struggling with something in this world of social isolation, and we need to have compassion for each other. We need to have understanding for each other.”

“Let’s not drive our people so hard. Know that everyone’s dealing with a lot of crazy shit right now. We have to roll with what we have, and do the best we can… but first and foremost, treat our people well and look out for the welfare our people,” he adds. “I think the biggest thing we do is listen, pay attention and recognize plans may change. That’s just the nature of the world right now.”

Everyone has awkward video call moments

Remember the guy whose kid came strutting into frame during a live BBC interview, instantly becoming a meme of legend? In 2020, we are all that guy.

Dogs bark. Babies cry. Our partners and roommates might have to dart by in the background — and we’ll do the same to them, at some point. Don’t stress it.

“We had a global all-hands last week,” says Jeff. “It was all done on Zoom, and… while I was talking, my kids ran in because it was breakfast time. And that was fine! I didn’t worry about it too much, and I ended up getting a lot of feedback from folks who were like, ‘wow, that was actually cool to see it happening to the CEO and not just to me.’ ”

You don’t always have to be on camera

Video calls are great. They help you connect with the people you’re talking to and bring back a bit of the body language we lose in text chats.

They can also be… a little bit exhausting.

“I’m already setting into this notion of Zoom fatigue,” Jeff tells me. “What’s the answer to that? Have some of your meetings by phone calls, instead of Zoom. You don’t have to feel like you’re always on camera.”

He adds that he’s been taking a good number of his phone meetings outside as “walking meetings” — even if we can’t go too far right now. “If you have the ability to go outside while still being connected, using either a phone call or Zoom on your phone, just changing up your environment is a good thing.”

Give everyone their own camera view

It’s good advice, even once we return to our offices: On video chats, try to give everyone their own camera — even if it means everyone has to find their own space to meet to avoid echoes. If you’ve got multiple people in one meeting room and a few dialing in remotely, it makes meeting dynamics weird; the people in the meeting room tend to talk among themselves, and it can be hard for remote folks to get a word in.
“We’ve long hypothesized — and we’ve heard from others who run virtual organizations — that we should have a rule that would say if one person is videoing into a meeting, then really everyone should be at their desk, one-to-one videoing into the meeting,” Jeff says. “So it’s not a roomful of people and one person who feels like they’re the outsider. Just make everybody on equal footing.”

“Now that we’re all using it one-on-one, and there’s no room with most of the people and one person is remote… we’re all getting a sense for how [well] this works.”

Being a good meeting participant might mean battling the algorithm

Most video chat platforms have algorithms that try to highlight whoever’s speaking, bringing them into the main view or drawing a green box around their head.

But these algorithms tend to just tune to whoever is loudest, missing the person who’s clearly been waiting to say something for five minutes. Want to have better meetings? Make sure that person gets to speak. Jeff says he’s seeing more and more of this as his team gets more comfortable with everyone being remote, calling it “better meeting hygiene.”

“When you’ve got a lot of people in a video setting, sometimes it’s hard for someone to raise their hand and get into the conversation,” he says. “What I’ve noticed is folks often pointing this out, and helping people to contribute to conversations. I think it’s actually helping to create a more diverse discussion — I’ve noticed people starting to say ‘hey, I think Caitlin had a comment. Caitlin, what were you gonna say?’ ”

Check in often

When everyone is heads down on work and we’re missing the random serendipitous conversations that happen in the elevator, it’s easier for issues to go unnoticed. Jeff says it’s important for leaders to be proactive about talking to their teams to figure out how they can help.

“Multiple members of the executive team have been doing round tables — virtually of course, with members of their teams,” he says. “Ten people in a Zoom room. Some of them do one a day, some of them do multiple a day, just to hear directly from our teams and see what they’re feeling.”

“That surfaces work issues, personal issues… There were employees in one country for whom the office just shut down very quickly and therefore they didn’t have their monitors or a work setup. So we’re able to identify that need very quickly and develop solutions of that. It’s just a matter of being able to listen and hear the things people are struggling with, and then to quickly as leaders turn around and act on those things.”

“[We] just have to be listening, and be on the lookout, and helping our employees through it,” he adds. “It’s not lost on me that one of our customers is Crisis Text Line. They allow people in moments of mental health crisis to reach out to a trained counselor over text to get help. They’ve been operating for, I think, six or seven years now. But their volumes are through the roof right now, with people who are just in social isolation needing someone to talk to because their anxiety is sky high.”

Outline your priorities to make better decisions

“Prioritization, and asking what is more important than what, is really the most important thing we do running a business to make decisions,” Jeff tells me. “You can say ABCD and E are all important; but if you don’t actually say in what order, and phrase them in a way that is understandable, and say, ‘this is more important than this,’ you really haven’t made decisions.”

Jeff tells me that Twilio uses a system they call BPMs — Big Picture, Priorities, Measures. These BPMs are meant to be the guiding light whenever there’s a decision to be made.

“We wrote one for our COVID-19 response because there’s a lot of decisions being made and a lot of ambiguity. So how do we do it? We wrote a BPM — I won’t go into details on it, but the number-one priority was the welfare and trust of our employees.”

“That’s where we start, and we feel a deep responsibility for the welfare of the 3,000 people who work for Twilio. First things first, have the welfare of employees in mind. Number two was customer success; through the process, make sure our customers are taken care of. But if our employees aren’t well taken care of, there’s no way we can take care of our customers. That’s why they’re priority number one.”

“You can imagine that various companies have different… I won’t point to any examples that you might’ve read about in the news, but there are certain companies that are being like ‘business at all costs!,’ ” he adds. “To me, that’s not the right priority driver.”

Let people be social!

Don’t worry too much about people slacking on Slack.

It’s a common mistake I see when companies shift over to doing more work remotely — they try to make Slack 100% work, 100% of the time.

Remember that for a lot of people — especially right now — the chatting they’re doing on Slack is the bulk of their daily social interaction. Let it happen! Embrace it. People need to just talk. Some of the most successful remote teams in the world have countless Slack channels dedicated to talking about TV shows and video games, and they get stuff done just fine.

Jeff tells me they’ve been encouraging massive, company-wide happy hours. “It’s kind of amazing,” he says. “You throw like, 100 people into a giant video room and do a happy hour and… bizarrely, it actually kind of works.”

“It’s not a business conversation,” he clarifies, “but it helps to connect people.”

Or get a little goofy with it: “We did our first cooking show. Whenever someone is cooking lunch, they could just be nominated, and they set it up and show us what they’re making.”

Have a dedicated place for people to find need-to-know info

Platforms like Slack are great for minute-to-minute conversations, but things tend to disappear. If there’s information that everyone needs to know, don’t count on them finding it buried among a million GIFs.

Figure out a solution for storing information that has a longer shelf life than your average Slack message. Maybe that’s a tool like Notion, or a custom solution like Zapier’s Async, or something a bit more straightforward.

“We have a Google Doc inside the company,” says Jeff. “It’s essentially our COVID-19 status page. And there’s a change log. So every day, any new things that are arising… there’s a daily change log at 5 p.m. Pacific. Everyone knows that is one place you go, just leave it up in your browser, and go back to it to see what changes there are.

On returning to an office

I was curious: After spending more than a decade in an office, how was Jeff feeling about this sudden shift to remote? What’d he miss? Would they go back to working in an office, once we’ve beaten this pandemic?

“I miss seeing people,” he says. “I think a lot of folks’ lifestyles are going to actually adopt more virtual work. I wouldn’t be surprised if we all come back and people are more likely to take a day or two a week and decide to work from home. We’ll know how it all works; it won’t be mysterious or scary, or like someone’s not showing up. It’ll just be… natural.”

“I wouldn’t be surprised,” he continues, “if there are some employees who say… ‘you know what? I actually really liked that. I don’t want to go back to the office.’ And you know what? I bet that’ll be okay.”

“I think there will be some folks who just can’t wait to return to the office — and that’s fine too!”