PaperStreet’s Annual Retreat: A Trip to Remember in Punta Cana 

A group of 20 people pose together for a photo on a wooden deck at night. Some are standing while others are crouching or kneeling in front. They are dressed in casual to semi-formal attire.

Ask any member of the PaperStreet team for one of the best perks of working here, and we’ll be quick to mention the company retreat. These are always productive trips that foster team building and ideas for the next year – even on the retreats where we’re hit with a hurricane

This year, we traveled to picturesque Punta Cana and had several days of sunshine, strategizing and socializing! Read what our team had to say about the trip: 

A remote worker since my first days at PaperStreet, I know how well our company runs in a virtual setting. That said, being able to meet in person – especially in a relaxing setting – is invaluable. Not only is it exciting to see the people whom you’ve grown close with, but it also sparks our creativity and fosters some work-related conversations that may not have arisen without the chance to bond together. – Nancy, Client Relations Manager

While remote work has its benefits, it is always great to see teammates in person. This is especially true when it’s in a tropical paradise. I am glad we can all come together to share our stories and success. – Pete, Founder and CEO 

A group of nine men, casually dressed, stand together and smile for the camera in a dimly lit, green-tinted space with a thatched roof in the background.

It was such a pleasure being able to meet my coworkers and spend time in a beautiful, tropical paradise. This time gave me an opportunity to bond with nearly all of my coworkers, whether we were talking about movies, video games, and even after-life theories. I’m grateful to have been invited to such a memorable and valuable trip – Jen, Graphic Designer

As someone who has been remote since day one at PaperStreet, it’s always nice to get to know teammates more intimately than the Brady Bunch-esque panels of a Zoom meeting. This was my third PaperStreet gathering, and it was great to see and bond with those I had connected with previously, never met in person, or only met in passing on previous trips. And to do so in a tropical setting with beautiful beaches only enhanced the experience. Looking forward to the next adventure! – Drew, Digital Advertising Manager

A group of people posing together on a beach at night, illuminated by colorful lights.

With all of us working remotely, it was a fantastic time getting to build deeper relationships with team members and discussing how to improve internal operations for an even better work environment. I have been at the company for a while and it is always a pleasure getting to see the familiar faces and also the new ones. Being able to go to an all inclusive resort as a team was such a great time and thoroughly enjoyed the experience. Can’t wait for the next team trip! -David, SEO Manager

It’s always good to get some quality face-to-face time with those you’ve been working with remotely for months (or in my case, years). And to be able to do it in a place as lovely as Punta Cana — what more can you ask for? I learn something new about everyone each year! – Adrienne, SEO Monthly Content Manager

I thought our annual team retreat to Punta Cana was a complete success!  Meeting everyone in person, connecting on a more personal level and having a few laughs (and drinks) along the way made this experience one for the books. I felt incredibly fortunate to be a part of a team that got along so well and had so many great ideas to share during the team building activities. I am truly looking forward to more team retreats in the future! – Stephanie Ashman, Graphic Designer

A group of people in casual clothing and blue hats are sitting in a room arranged for a meeting. One person stands speaking, others are seated with laptops and notebooks.

Remote work has many positives and negatives, but nothing beats in-person teamwork and team bonding. Our annual retreats provide a great opportunity to catch up with team members on their lives outside of work and to meet new team members that have joined. Punta Cana was a remarkable venue filled with great team building activities. Looking forward to the next annual trip. – Robin Tidrick, Sales Director

Our retreat in Punta Cana was an amazing experience that brought our all-remote team together in person.  I enjoyed the shared experiences, from team-building activities to casual conversations by the pool. It was wonderful to get to know everyone on a professional and personal level.  Can’t wait for the next one.  Liz Cossin, Bookkeeper

Four women stand together under a thatched roof structure at night, all smiling and wearing colorful summer dresses.

I spend the majority of daylight hours working with the PaperStreet team each week, and it is such a joy to see them face-to-face. Being physically present with my remote team sparks some excitement for the new year and reminds me of the badass people I work with each day. It was a few days of sunshine, cold drinks, good company and productive conversations! – Allison, Content Director

It was great to meet the team that I work with every day. Being on the blue ocean with good food, cold drinks, and fun people made the trip one to remember. I am looking forward to the next time we all get to do something like this again.  – Caleb, SEO Associate 

The value of meeting face to face simply cannot be replaced. Ideas, conversations and team building just flow so much easier. An all-inclusive tropical retreat was just the icing on top (of our endless food choices). I cannot say enough positive things about our PaperStreet get together. At the end of the day, businesses are powered by people and people who are genuinely connected just do better all around. – Elyssa Helfman, Creative Director.

A candle, a dish with three different condiments each with a small white spatula, and a sign with a blue logo featuring a stylized leaf, atop a table.

I had a wonderful time seeing people I work with every day virtually in person. Some of my coworkers I had not met before and some I had not seen in a few years. For a team that is fully remote, a trip like this is wonderful for bonding and getting to know each other better outside of our usual workflow. Having a few days as well to enjoy the beach was great. I live in Boston where the weather is not fun this time of year. Overall I had a really nice time and look forward to next year. – Andrew, VP and Web Director

It was really nice seeing familiar faces and meeting others for the first time. Everyone got to know each other on a more personal level outside of work which we don’t normally get to do. We participated in a bunch of activities, such as snorkeling, archery, and trapeze in a circle school they had.

– Ian Garcia, Web Developer 

I’ve been at PaperStreet for 3 years now and had not met anyone at the company in person with the exception of one. It was so great to be able to meet everyone, get to know their in-person personalities, and spend some quality time with people I work with every day. I’m a rather shy person at first but I’m glad I got the chance to break out of my shell a bit. I’m very much looking forward to the next time we can all get together again. – Kat Dinges, PPC Associate

Le point culminant du voyage était les belles plages. [The highlight of the trip was the beautiful beaches.] – Chris De La Vega

A sandy beach borders clear blue water under a bright sky. Two sailboats are visible in the distance.

It is always great to see everyone on our annual trip. Each time, it is a lot of fun catching up and sharing laughs. You can’t beat the perfect weather and beaches in Punta Cana either. – Kyle

“Annual retreats” have this odd, corporate connotation to them. Yet, when you work in a smaller, more familiar company, our annual work trip takes on a different meaning. It provides team building that you can’t obtain from remote life. It builds connections from personal conversations that you may otherwise not have. In such a great picturesque setting, it fosters creativity and innovation when we bond together on ways to come up with new features, process improvements, and learn from challenges in the past. It is a yearly highlight to solidify our company culture, while refreshing and recharging. – Alex, Internet Marketing Director, VP

It was awesome finally getting to meet almost everyone in person! It really is an experience that can’t be replicated through a screen. My personal favorite part of the trip was the late night stargazing I was able to do with a few people. Since we were so close to the equator, we were able to watch the moon and stars actually move through the sky. It was so clear I was able to show them a few constellations! We also got to watch the moonrise over the ocean as if it was the sun early in the morning! – Rob, Junior Web Developer

A moonlit beach scene with waves gently lapping against the shore. The sky is partially covered with clouds, and the sand in the foreground has sparse seaweed.
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