How CoverWallet maintains company alignment

The CEO of the insurance technology platform shares how teams can stay in sync

Achieving company alignment is hard enough when you’re a small company and everyone’s in the same building. But when your business expands to include hundreds of employees across four time zones, you risk losing the communication, spirit, and values that inspired you to start a company in the first place.

Keeping her company’s communication and culture in place across continents—and knowing whether she’s doing it right—keeps CoverWallet cofounder and CEO Rashmi Melgiri up at night. CoverWallet is the first online platform where small businesses can buy insurance online. But leading a fast-growing company has plenty of challenges, as Melgiri explained to host John Henry in Episode 3 of the Up At Night podcast.

Managing rapid expansion

Melgiri started the company four years ago in New York City, and it has since grown to 300 employees and four offices in three countries, serving tens of thousands of customers. But whether the remote office is in Australia, Spain, or in Rochester, New York, the same question sticks in Melgiri’s head.

“How do we manage keeping everyone connected and on the same page about what we’re trying to do?” Melgiri said. “So that we’re not becoming a series of franchises in different markets, but it’s all the same CoverWallet look and feel and principles in each one.”

The answer is made more complicated because it’s not the same each time. For the one company executive based in Australia, the biggest challenge is keeping him from burning out after working 14-hour days to support regions around the world. For the rest of her company, Melgiri has to figure out how to disseminate information to local teams and empower them to get stuff done.

Even when an office is relatively close—Rochester is a five-and-a-half-hour drive from CoverWallet’s New York City headquarters—maintaining company alignment can still be challenging. 

How do we make sure that they don’t feel like they’re out there alone?

Rashmi Melgiri, Cofounder

“How do we make sure they don’t feel like they’re out there alone?” said Melgiri, who chose to expand CoverWallet’s agents and sales team to Rochester, not only to escape the high cost of real estate in New York City, but to take advantage of Rochester’s existing insurance talent. “We try to be diligent about making sure there are senior people that go to these offices on a regular basis. They’re part of the original group that lives by the culture and can speak about the highest things that are going on. Even with as many teleconferencing tools that we have, there’s no replacement for an in-person visit.”

Transparency as a tool for alignment and accountability

There is one secret weapon that Melgiri has found to unite all the locations and keep that thread of communication going: a daily meeting with the entire company at 8:30 a.m. ET. Nearly everyone at CoverWallet is either in the room or on the phone at the same time every day. (The executive in Australia, where it’s the middle of the night, gets a pass.)

The meetings cover the usual material: celebrating birthdays, work anniversaries, promotions, and company announcements. But the biggest chunk of time is devoted to covering key metrics from each part of the company. Looking at metrics on a daily basis, rather than weekly or monthly, lets CoverWallet diagnose and solve business problems quickly. 

If you’re not looking at [metrics] for a week at a time or a month at a time, then you’re not actually working on it, right?

Rashmi Melgiri

“The visibility on those metrics gives you the chance to actually improve them,” Melgiri said. “If you’re not looking at it for a week at a time or a month at a time, then you’re not actually working on it, right? So as soon as the number is very off from where we think it is, people are addressing it that day and they have an answer to it the next day.”

Transparency drives every topic at these meetings. Melgiri said the company often hears about company strategy before CoverWallet’s board does.

“Every time we have a board meeting—all the big topics that we talk about, the big strategic questions of the company?” she said. “We actually have those discussions [first] with the whole company. Usually the day after we present to the company, it will be presented to the board.”

That level of openness with 300 employees takes a lot of effort. Melgiri compared the daily morning meeting to exercise: She doesn’t always want to do it, but she’s always glad she did.

I sometimes ask myself would I do it all again? Would I start another company knowing how much work this was? My answer right now is yes, I would do it all over again.

Rashmi Melgiri

But also like exercise, you want to know whether it’s working. And in the blur of daily meetings, multiple time zones, and tens of thousands of customers, it can be difficult for Melgiri to see what ultimate success looks like in terms of maintaining company alignment.

“I never have an answer for that. I sometimes ask myself would I do it all again? Would I start another company knowing how much work this was?” Melgiri said. “My answer right now is yes, I would do it all over again.” Listen to Melgiri’s Up At Night podcast episode here, and read the full transcript here.

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