Just In TechCrunch: Sidekick raises $2.3M to make remote work more human

Sidekick's new mission:
Make remote work human

December 9, 2020
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Hi friends!

It's been a roller coaster of emotions for team Sidekick since we wrapped up YC in September. But I'm excited to share our new mission, some lessons we've learned and some cute photos of cats on Sidekick.

We built Sidekick as an always-on video device to make remote communication more efficient (our old website). We've pivoted our mission to make remote work more fun and human, with a focus on helping growing teams.

Good-bye to "Always-on Video", Hello to "Coworking Sessions"

With this new mission, comes a new way to use Sidekick. The product is now built to be used for "Coworking Sessions", where the team is on Sidekick with the video call running on Mon, Wed, Fri from 2-5pm.

This is the right balance of face time. Without Sidekick, all communication is transactional and work-related - there's no space for the human conversations we all crave. However, 8 hours of Sidekick a day can be too much - it gets rid of all the flexibility and goodness of remote work. "Coworking Sessions" follows the Goldilocks principle, it's just the right amount of facetime to make remote work fun and not isolating.

With Sidekick, you can see your teammates throughout the day, so it doesn't feel like you're working alone in a basement. You can chat about The Bachelor, introduce everyone to your cats and get to know each other as real people. Sidekick keeps your growing team tight-knit and makes sure everyone feels supported while we're all quarantining.

1 month after YC (Oct) - We ignore our power users

Coming out of YC, we were convinced that we wanted to be a communication tool. We had built Sidekick to simulate the office to make communication more efficient.

We had 100s of different users from all sorts of backgrounds — most were churning and it was depressing. In early October, we went on the hunt to find a mythical group of users that actually needed constant communication to get their jobs done. We were talking to teams doing recruiting, CX, finance, day traders, legal and half a dozen more.

At the same time, we were ignoring our YC training by not actually listening to our power users. Our power users loved Sidekick because it made their teams feel closer, it made them less lonely and it helped everyone feel like they belonged.

Us being stubborn founders, we bucketed these users as "fake users" (no offense to anyone reading this). There's no way anyone would pay money to help build team camaraderie, right? Right...?

November - We (mostly) stopped being stubborn idiots

At the end of October, we still had not found our mythical users that need constant communication. Morale was at an all time low and I personally was in a deep, dark place.

So you know what I did? I got ramen with one of our users Will, the CEO of Karat. He finally got through to my stubborn brain when he said this:

"We're missionaries, not mercenaries. We're hiring really smart people, but if they just wanted a 9-5 remote work job, they would have gone to Google. We have to offer more than just a paycheck."

- Will Kim (Karat, YC W20)

I went and talked to a bunch of other founders and everyone said the same thing. Founders were struggling to build a sense of camaraderie and community while remote.

The wheels started turning. On November 7th, the Sidekick founders had a 6 hour existential conversation. We came out of it with our new mission: make remote work human.

Turns out, founders really care about remote team camaraderie

This new pivot is working. In the month of November, we changed the product so that it's built for coworking time, not always-on video. We changed our website and our pitch. Our sales grew 2.5X in the month of November, and we landed big companies like Brex, Mercury and Feather.

If you're one of our early users, we're eternally grateful for all you've taught us. I know we were stubborn, but eventually we got there. We've learned two valuable lessons through this whole experience:

Fun new features coming soon!

We're cooking up some really fun stuff! Going down this path of being a remote camaraderie tool has given us the focus to build some truly novel features. I'll outline our favorite one below:

The Virtual Kitchen

At the kitchen at my old company, we had a giant puzzle. Over the span of months, people would stop by and add a few pieces. Often, a crowd would form around the puzzle (I know, I miss crowds too). In these spontaneous moments, you got to meet new people or bump into old friends you haven't seen in a while.

These magical moments just don't exist while we're remote, but we can bring them back. As a user of Sidekick, if I want to take a break, I'll go add a couple words to the crossword puzzle in the virtual kitchen. Someone else at the company might also take a break and come join me in the kitchen. Boom, we brought serendipity back to remote work.


Lastly, some fun pictures from our teams (and their cats)

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