Behind The Scenes: Peachy's First On-Site

Lex interviews Peachy's chief of staff, Nate Elliott, about the team's first on-site.

October 20, 2021

At the end of September 2021, the entire Peachy team met in person for the very first time. It was a meeting the team had anticipated for months. And when it finally happened, it was... let's just say more than a little exciting. To chat about Peachy’s very first on-site and dig into what made it work, Peachy’s CEO Lex Oiler sat down to interview her chief of staff, Nate Elliott, the man behind the on-site...

Lex: So, what was it like meeting the team in person after all this time?

Nate: It was less weird than I thought it would be, to be honest! I always get a little nervous about meeting people IRL for the first time, but I was blown away by just how quickly everyone seemed to make the online to IRL transition. It all felt so natural. The strangest thing was just seeing everyone from the shoulders down! It was funny to realize how tall (and not tall) everyone is!

Lex: Can you tell me about the planning process?

Nate: We actually threw the whole thing together really quickly. I remember hearing rumblings about something tentatively planned for the end of September back in July, and we finally solidified the dates on August 30th. Still, it wasn't until September 11th that I finally got the go-ahead to start booking everything! That gave me just 17 days to get everything planned. We had to buy flights, book lodging, figure out meals, and nail down an itinerary.

It turned out to be a really fun challenge, the biggest of which, by far, was lodging. We debated pretty heavily between booking an Airbnb and going the hotel route. We really wanted to have some sort of common space where the team could hang out and work, and also give the team the privacy of having their own room. While the AirBnBs we looked at were really, really incredible, we felt strongly that each teammate should have their own room, and finding a nine-bedroom home in LA (basically two weeks in advance) wasn't easy. Fortunately, we found what felt like a perfect solution at the Ace Hotel in Downtown Los Angeles. We booked their biggest suite to use as an office/hangout area. It had a big terrace with a sweet view of the city and ended up being a pretty perfect location for us. I think it was much more fun than working out of a conference room!

Once we had the location and lodging sorted out, everything after that was pretty easy.

Lex: What sort of activities did we do?

Nate: Interestingly, we had initially planned the on-site around an event we had a booth at, LA Tech Day. Then, about a week before the on-site, it was canceled! While this was kind of a bummer, it ended up being for the best! It essentially gave us a whole extra day to spend as a team getting to know each other, without the distractions of a conference!

And as this was the first time that our entire team had been in the same place, a big focus of the on-site was team-building and relationship-building. For some of us, myself included, it was the first time meeting anyone on the team in person, so we spent a lot of time just chatting and getting to know each other. I think this time has already begun to pay dividends, as our team now has more unity and clarity around communication than before!

Beyond just hanging out, we also did some more formal activities, like reviewing our newly-drafted employee handbook and our Q4 strategy doc. As a remote team, having the chance to sit in the same room and talk through some really important topics was wildly helpful.

We also did some cool get-to-know-you games that I put together. I’m not sure the team thought they were as cool as I did...

Lex: Yes, we did.

Nate: I’m glad! It was really fun to have some forced depth to our get-to-know-you conversations. I put together an introduction deck that I used to introduce each teammate. While on its face it might seem a bit silly to introduce everyone after we’ve all been working together for months, it revealed a lot of fun info that probably wouldn’t have come up in conversation. Then, by adding in a game of “two truths and a lie,” we were able to get to know each other pretty well in a pretty short amount of time!

Lex: What was the most surprising thing you learned about a teammate?

Nate: Our team is full of really amazing people. For example, we have a 7x All-American collegiate gymnast on our team, a competitive bowler, an extreme road tripper, a game show contestant, and a DECA national champion, amongst other remarkable individuals. We really do have an amazing team full of amazing people!

But honestly, the most surprising thing I learned was that PJ, our CTO, has never read Harry Potter or watched Star Wars. Absolute insanity.

Lex: What was your favorite moment of the trip?

Nate: It's so hard to choose just one, but the moment that we realized that we'd processed our first payment was really, really special. It's honestly a moment that I think I'll look back on for the rest of my life as really meaningful. There's this song in the musical Hamilton where Aaron Burr is basically lamenting about how he wants to "be in the room where it happens" and that moment had a very "room where it happens" feel to it. For so long I’ve looked longingly at these incredible startups that are changing the world. I’ve read the books telling their stories and thought, "How cool would it have been to be in the room when that important event happened?" And one day, when the book telling the story about Peachy is written, I have a feeling that moment is going to be a very special scene to write.

Lex: What was the most challenging aspect of the trip?

Nate: Honestly, the hardest part was getting the team to fill out the get to know you questionnaires! 🤣 🤣 🤣  It was like pulling teeth to get some people (cough Lex and Austin cough) to complete them. However, I'm a pretty determined person so I was able to get the info out of you two eventually!

Lex: What will we do differently next time?

Nate: I don’t think we’ll change too much moving forward. We did a quick survey afterward and the team unanimously agreed that it was enjoyable, a good use of time, and helped them feel closer to their teammates. To me, that means it was a success. But even better, the entire team said they were looking forward to the next one! Talk about a win!

A few teammates did mention that they wanted a bit more time, so I wouldn’t be surprised if we do one more night next time. I also think we’ll begin exploring different locations in the future. Downtown LA was a great first location, but we have teammates in 5 different states! So the idea of moving these to different locations around the US is definitely something we’re thinking about!

Lex: Do you have any tips for other companies considering doing their own on-site?

Nate: Just do it! It doesn’t need to be complicated or fancy or anything like that. Just get your team under the same roof and let them get to know each other, as people. Laugh together. Eat together. Work together. It’ll help you appreciate each other more, communicate better, and work more effectively–I know it did for us!

Published on: 
October 20, 2021

Note: This is not to be taken as tax, legal, benefits, health or financial advice. Since rules and regulations change over time and can vary by location, consult a lawyer or financial expert for specific guidance.

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