CEO on what works with remote work

In late 2019, as CEO of Austin-based insurtech firm The Zebra, I signed a multi-year lease on a 43,000 sq. foot workplace area. This was 4 instances the scale of our outdated one. Our enterprise was thriving and on tempo to double our 200 individual headcount.

Our tradition was thriving. Normally, I’m not an enormous fan of attributing success to onerous to explain “tradition.” Nonetheless, our staff lived and breathed our “All Stripes Welcome” mantra and labored nicely collectively.

Just a few months later, contemporary off a Collection C fundraise, the corporate was able to enter hyper-growth mode. Then, virtually in a single day, all the pieces on the planet modified, and I noticed that I wanted to determine methods to preserve this amorphous factor known as tradition. There was actually nothing within the “CEO handbook” about how to do that.


First, I had to consider what tradition meant at The Zebra and what we would have liked to focus on. In the end, it’s connection and belonging. We wanted to determine methods to preserve the sensation that when somebody joins The Zebra, they turn into a part of one thing.

The second was the query of whether or not to go remote completely. How would this alteration our tradition? How may we protect it amid such change? I had a bonus since I used to be a remote CEO working an organization based mostly in a distinct state. Zoom fatigue was actual for me earlier than SNL made skits about it.

Regardless of this firsthand perception, our firm actually didn’t get all the pieces proper once we determined to go all-in on remote optionally available work. Now that we’re over a yr and a half in, I wished to reveal a few of these successes and failings which can be changing into a part of my so-called CEO handbook.

What labored

Orientation: Use orientation as proof that you simply stroll the stroll to new staff. Share the fundamentals, however go a step additional and anticipate their wants as remote employees. Allow them to know who to contact for additional t-shirts or solutions to much less formal questions like: “Is it a digicam on or digicam off Zoom tradition?” Present them the insurance policies you’ve drafted to make sure all staff are created equal, regardless of the place they work.

Accessibility: Transparency is one among our firm values. Rather than my pre-pandemic CEO dinners, the place I gathered one worker from every division for a small dinner we use a program that units up 15- or 30-minute “pace courting model” Zoom requires these prepared to satisfy new folks on the firm. The entire government staff participates, and it retains us on our toes not realizing who we’ll be matched with. This format helps mimic a number of the impromptu “hellos” on the water cooler and is much less intimidating than throwing half-hour on the CEO’s calendar (though I’d welcome that).

Empathy: On Monday mornings, it’s not unusual to seize a espresso within the cafeteria and listen to chatter about everybody’s weekends. These experiences provide unplanned glimpses into staff and their private lives as an actual reminder of their priorities. I used to be nervous that going remote would lose these unplanned connections, however because it seems, I had nothing to fret about. When a brutal winter storm hit Austin and knocked out utilities for greater than 1 million folks, I noticed our staff scramble to distribute a sign-up sheet providing their houses to coworkers and their youngsters and pets. They supplied this help to strangers, whose solely connection is that they share a office, in a pandemic no much less. That’s the second I knew our tradition was robust. My greatest studying at that second was that you simply couldn’t pressure tradition.

What didn’t work

Over-the-top gifting: To reflect a number of the enjoyable actions and perks of workplace life, we moved our budgets round to permit numerous inside tradition golf equipment to ship items to staff. A “pamper your self” package, flashcards of encouragement, snacks, and a Valentine’s Day reward. We bought about 4 deliveries in 5 weeks and knew we’d gone overboard. Take a second to consider what issues: is it a shock within the mail, or is it a three-hour early launch on Fridays? Is it an organization rule to dam midday to at least one o’clock for a compulsory lunch break, or is it a present for Worker Appreciation Day? The reply lies inside your worker base and anticipating what they worth most.


Compelled enjoyable: You possibly can’t mimic an in-office setting in a remote setting. We examined a program that mirrored our workplace in a digital setting for workers to satisfy on this digital world and mingle. Most of our workforce began through the pandemic and had by no means set foot within the workplace. So, this expertise didn’t imply a lot to them. Barely anybody confirmed as much as these gatherings, and to make issues worse, ending a dialog there meant harshly slicing off a Zoom name as a substitute of excusing your self to introduce your self to somebody new who simply walked in. It was awkward at finest, and it simply felt impolite. Digital gatherings must be natural and voluntary for true bonding to occur.

It’s been fairly the educational expertise as CEO throughout this unusual time. I oversaw one other fundraising spherical and our firm catapulted to the coveted “unicorn” standing. We’re nonetheless hiring for tons of open roles. However, now I’ve bought some new pages to reference in my CEO handbook, and I’m positive I’ll be including extra.

Keith Melnick is the CEO of The Zebra.