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Our company went all in on remote work. Here’s what worked (and didn’t)

The CEO of The Zebra oversaw a fundraising round, the move to unicorn status, and is still hiring despite the pandemic. Here’s what he learned about forced fun vs. the value of 15-minute Zoom calls.

Our company went all in on remote work. Here’s what worked (and didn’t)
[Source Photo: Tima Miroshnichenko/Pexels]

In late 2019, as CEO of Austin-based insurtech company The Zebra, I signed a multi-year lease on a 43,000 square foot office space. This was four times the size of our old one. Our business was thriving and on pace to double our 200 person headcount.

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Our culture was thriving. Usually, I am not a big fan of attributing success to hard to describe “culture.” However, our team lived and breathed our “All Stripes Welcome” mantra and worked well together.

A few months later, fresh off a Series C fundraise, the company was ready to enter hyper-growth mode. Then, almost overnight, everything in the world changed, and I realized that I needed to figure out how to maintain this amorphous thing called culture. There was certainly nothing in the “CEO handbook” about how to do this.

First, I had to think about what culture meant at The Zebra and what we needed to focus on. Ultimately, it’s connection and belonging. We needed to figure out how to maintain the feeling that when someone joins The Zebra, they become part of something.

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The second was the question of whether to go remote permanently. How would this change our culture? How could we preserve it amid such change? I had an advantage since I was a remote CEO running a company based in a different state. Zoom fatigue was real for me before SNL made skits about it.

Despite this firsthand insight, our company certainly didn’t get everything right when we decided to go all-in on remote optional work. Now that we are over a year and a half in, I wanted to divulge some of those successes and failings that are becoming part of my so-called CEO handbook.

What worked

Orientation: Use orientation as proof that you walk the walk to new employees. Share the basics, but go a step further and anticipate their needs as remote workers. Let them know who to contact for extra t-shirts or answers to less formal questions like: “Is it a camera on or camera off Zoom culture?” Show them the policies you’ve drafted to ensure all employees are created equal, no matter where they work.

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Accessibility: Transparency is one of our company values. In place of my pre-pandemic CEO dinners, where I gathered one employee from each department for a small dinner we use a program that sets up 15- or 30-minute “speed dating style” Zoom calls for those willing to meet new people at the company. The whole executive team participates, and it keeps us on our toes not knowing who we’ll be matched with. This format helps mimic some of the impromptu “hellos” at the water cooler and is less intimidating than throwing 30 minutes on the CEO’s calendar (even though I’d welcome that).

Empathy: On Monday mornings, it’s not uncommon to grab a coffee in the cafeteria and hear chatter about everyone’s weekends. These experiences offer unplanned glimpses into employees and their personal lives as a real reminder of their priorities. I was worried that going remote would lose those unplanned connections, but as it turns out, I had nothing to worry about. When a brutal winter storm hit Austin and knocked out utilities for more than 1 million people, I saw our employees scramble to distribute a sign-up sheet offering their homes to coworkers and their children and pets. They provided this assistance to strangers, whose only connection is that they share a workplace, in a pandemic no less. That’s the moment I knew our culture was strong. My biggest learning at that moment was that you couldn’t force culture.

What didn’t work

Over-the-top gifting: To mirror some of the fun activities and perks of office life, we moved our budgets around to allow various internal culture clubs to send gifts to employees. A “pamper yourself” kit, flashcards of encouragement, snacks, and a Valentine’s Day gift. We got about four deliveries in five weeks and knew we’d gone overboard. Take a moment to think about what matters: is it a surprise in the mail, or is it a three-hour early release on Fridays? Is it a company rule to block noon to one o’clock for a mandatory lunch break, or is it a gift for Employee Appreciation Day? The answer lies within your employee base and anticipating what they value most.

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Forced fun: You can’t mimic an in-office environment in a remote setting. We tested a program that mirrored our office in a virtual setting for employees to meet in this digital world and mingle. Most of our workforce started during the pandemic and had never set foot in the office. So, this experience didn’t mean much to them. Barely anyone showed up to these gatherings, and to make matters worse, ending a conversation there meant harshly cutting off a Zoom call instead of excusing yourself to introduce yourself to someone new who just walked in. It was awkward at best, and it just felt rude. Digital gatherings have to be organic and voluntary for true bonding to happen.

It’s been quite the learning experience as CEO during this strange time. I oversaw another fundraising round and our company catapulted to the coveted “unicorn” status. We’re still hiring for tons of open roles. But, now I’ve got some new pages to reference in my CEO handbook, and I’m sure I’ll be adding more.


Keith Melnick is the CEO of The Zebra.

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