Inside Crooked Monkey: How Our Company Culture Keeps Us Connected

At Crooked Monkey, we may work remotely, but we’re never far from each other. Scattered across different countries and time zones, our team isn’t just connected by emails and chat messages. We’ve built a company culture that keeps us close, no matter the distance. As we celebrate 20 years of success, we’re proud of the strong connections we’ve fostered along the way.

As a company that specializes in custom swag and corporate gifts, we understand the importance of staying connected. Whether it’s personalized merchandise or unique branded products, our custom swag helps foster a sense of belonging and strengthens our team bond, even from miles away.

A Remote Team That Feels Like Family

The beauty of working remotely is flexibility. But let’s be real—without a solid company culture, it can feel isolating. That’s why we go beyond just “staying in touch.” We celebrate birthdays, not just with a generic message, but with a full-blown virtual party—Crooked Monkey style. That means singing our own birthday song, with each line in a different language. It’s chaotic, it’s hilarious, and it’s us.

The Annual Retreat: When Virtual Becomes Reality

Once a year, we swap our home offices for a real-world adventure. Our company retreat is where we finally get to see each other beyond the screen. It’s a time for brainstorming, bonding, and making memories that fuel us for the rest of the year. Sneak peek of our last retreat here.

Happy Hours, Challenges, Memes and a Little Bit of Madness

We host virtual happy hours where we play games, tackle bizarre challenges, and just hang out. Whether it’s trivia, scavenger hunts, or completely made-up competitions, there’s always something unexpected (and slightly ridiculous) happening. And then there are our themed challenges—wild makeup looks, crazy hats, and costumes that make us cry with laughter. Some of us take it way too seriously (and we love them for it). All of this is part of our vibrant company culture, keeping things fun and connected, no matter the distance.

If there’s one thing we love, it’s a good meme. Actually, scratch that—we create good memes. Our team chat is flooded with inside jokes, ridiculous GIFs, and the kind of humor that only makes sense if you work here. But we took it to another level with a recent happy hour challenge: recreating famous memes using our own clothes, poses, and sheer creativity.

The results? Pure gold. These homegrown masterpieces became a viral sensation within Crooked Monkey, and now they’re part of our daily conversations. Here are some of the gems…

Our Tips for an Awesome Company Culture – Keeping a Remote Team United

So, how do we stay so connected? Here are some key takeaways:

• Make space for fun: It’s not just about work—inside jokes, games, and shared moments build real connections.
• Not every call is work related: Celebrate birthdays, wins, random announcements—if there’s a reason to celebrate, go with it.
• Encourage creativity: Whether it’s a meme contest or a wild costume challenge, letting people show their personality keeps things fresh.
• Swag matters: A killer hoodie, a custom mug, some cool socks, or even a branded water bottle—having shared gear like personalized merchandise makes a remote team feel like a team. Custom swag not only boosts morale, but also strengthens our connection, showing off our unique company spirit and shared identity.

For more on staying connected and making remote work work, check out our blog post: The Ultimate Guide to Remote Work.

Want to bring this kind of energy to your team?

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