Dagger Team Offsite 2024: Strategy, Collaboration, and Connection
October 30, 2024
Oct 30, 2024
Sophia Sanders
None
It’s a huge investment to fly our entire team from the four corners of the earth to get together for our annual offsite. Is it worth it? Undeniably yes, but, a lot of work goes into making sure we get the ROI we hoped for. Our recent team retreat was more than just a rare opportunity for face-to-face collaboration, it became a pivotal moment for aligning on strategy, strengthening team bonds, and sparking fresh ideas that will drive our next chapter. The pressure to deliver is real, but so are the rewards when it all comes together.
With three annual retreats under our belt, we’ve learned some valuable lessons we’ll share in the hope that they might be helpful to others.
This year, we chose Oceanside, California, just north of San Diego, and stayed at The Seabird Resort & Spa - and I can’t recommend this venue enough. It truly exceeded our expectations in every way.
How we spent our time:
Sunday: Arrival and Welcome Reception
Monday: Strategy and Priorities Discussion – Aligning on key goals and unconference in the afternoon
Tuesday: Hackathon – Encouraging creativity through hands-on projects
Wednesday: Team Culture and 2024 Retro – Reflecting on what works and what to improve and unconference in the afternoon
Thursday: Fun Day – Scavenger hunt, relaxing, and bonding as team
Tips:
#1 - Discussions over presentations. Your team likely already has regular meetings to cover status updates, quarterly reviews, and other routine matters—so leave those behind. Save them for your usual remote 9-to-5 schedule. Our unspoken rule was simple: "If it's something you can cover in a typical team call, it doesn't belong here." Now that you're all gathered together, use this opportunity to focus on presentations that spark meaningful conversations and inspire collaboration.
#2 - Take a day to get creative. Given that our team and product are both highly technical, a hackathon is the perfect way to tap into everyone’s creativity. We invited each person to bring an idea, and from 9am to 10pm, they had the entire day to bring it to life. Some people teamed up, while others zoned in with their headphones and hacked solo. Some of our non-technical team members even used the time to take an “Intro to Coding” course!
We wrapped up the day with an hour-long demo session, where everyone showcased their finished projects. It was inspiring to see how excited the team was to share their work and celebrate each other’s creativity.
#3 - Give space to openly discuss team culture. Our co-founder Sam sends a culture survey to the team every year, and gives a short presentation on the results to facilitate discussion during the retreat. We paired the presentation with an interactive “2024 retro” this year, and used Parabol to upvote the topics people wanted to discuss.
We used the bulk of the session to talk openly about things we want to change or improve in the way we work. Despite many wonderful aspects of our culture, there are always things that can be tweaked. As the team grows, what might have worked a year ago may not be working for everyone today. Open and frank conversations are critical to ensuring the team continues to work well together. It’s important that everyone, including senior leaders, show an open-ness to hearing what’s not working, and a willingness to adapt their personal preferences for the greater good.
#4 - Book a meeting space with lots of windows. A beautiful location adds to the cost, but pays for itself in terms of inspiration. No one wants to spend their day in a dark and dreary conference room. We went to the extreme - choosing a room with so much natural light that it made using our projector a challenge… Next year, we’ll fix that by renting a large TV, so we can enjoy the sunlight without sacrificing visibility.
#5 Unconferences might work for you, but consider the timing when collecting topics. This year, we tried an unconference style for part of our retreat since we weren’t sure which topics would be most important to everyone. We asked the team to write down topics they wanted to lead, and then we organized the sessions based on their submitted ideas.
In theory, this works, but we discovered a problem. We had asked for topics before having done the strategy session. After the strategy session, it was clear that what we most needed to talk about had changed. Rearranging the unconference schedule that we had put together the night before wasted valuable time.
In the end, it worked out, but be aware that unconferences add extra pressure on both senior leadership and the Ops team. Unlike other activities, unconferences can’t be fully organized before the retreat begins, so flexibility, and quick thinking are key.
#6 Swag bags + welcome reception will set the tone for the rest of the week. Our entire team arrived on Sunday, and were greeted by beautifully prepared swag bags from our Ops team as we stepped into the welcome reception. This reception has become a staple in our retreat agenda, as it’s often the first time of the year many of us see each other in person. With everyone arriving around the same time, the reception sets an inclusive tone for the rest of the week, and offers a perfect chance to reconnect and kick off the retreat on the right foot. It’s a chance to celebrate the past year’s efforts, show gratitude to each other, and remind ourselves why we’re so fortunate to be part of this great team.
#7 Get back to the basics for team activities. People naturally want to unwind and connect, but it helps to provide activities that spark non-work related conversations.
One night, we organized a game night at a local sports bar. We kept it casual with trivia cards, Jenga, and a private room setup with a simulator where people could play soccer, golf, or even zombie dodgeball. It wasn’t anything fancy, but it turned out to be a huge hit! The activities were laid back enough for everyone to join in, while also giving those who preferred to sit back and watch a chance to relax and enjoy the vibe.
#8 Allow a full non-work related team bonding day. As you can probably tell, team cohesion is incredibly important to us. On our final day of the offsite, we partnered with a third party event company to organize a scavenger hunt in La Jolla, complete with lunch integrated into the activity. It was a perfect blend of friendly competition and exploration of the town together. A lively happy hour, followed by a beautiful waterfront dinner as the sun set, provided an unforgettable way to close out a special week.
As we wrapped up our third annual retreat, it was clear just how valuable these in-person gatherings are for a fully remote team like ours. From the creative spark of the hackathon to the friendly competition of the scavenger hunt, every moment reinforced the importance of connection, collaboration, and forward-thinking outside of our usual virtual meetings. These unconference sessions allowed us to focus on critical strategy, sparking innovative ideas, and guiding the future direction of our company.
It’s not just about the work - it’s about fostering relationships, sharing experiences, and making memories that will energize us long after we return to our remote routines. With each offsite, we learn more about what works best for our team, and we’re already excited for next year’s adventure!
If you’re planning your own retreat or offsite, remember to create space for meaningful conversations, strategic thinking, and spontaneous fun. Ultimately, the real impact of these retreats comes from bonds we build, strategies we refine, and the renewed energy to carry back into our everyday work.
By the way, we are hiring! Check out our open roles here.
It’s a huge investment to fly our entire team from the four corners of the earth to get together for our annual offsite. Is it worth it? Undeniably yes, but, a lot of work goes into making sure we get the ROI we hoped for. Our recent team retreat was more than just a rare opportunity for face-to-face collaboration, it became a pivotal moment for aligning on strategy, strengthening team bonds, and sparking fresh ideas that will drive our next chapter. The pressure to deliver is real, but so are the rewards when it all comes together.
With three annual retreats under our belt, we’ve learned some valuable lessons we’ll share in the hope that they might be helpful to others.
This year, we chose Oceanside, California, just north of San Diego, and stayed at The Seabird Resort & Spa - and I can’t recommend this venue enough. It truly exceeded our expectations in every way.
How we spent our time:
Sunday: Arrival and Welcome Reception
Monday: Strategy and Priorities Discussion – Aligning on key goals and unconference in the afternoon
Tuesday: Hackathon – Encouraging creativity through hands-on projects
Wednesday: Team Culture and 2024 Retro – Reflecting on what works and what to improve and unconference in the afternoon
Thursday: Fun Day – Scavenger hunt, relaxing, and bonding as team
Tips:
#1 - Discussions over presentations. Your team likely already has regular meetings to cover status updates, quarterly reviews, and other routine matters—so leave those behind. Save them for your usual remote 9-to-5 schedule. Our unspoken rule was simple: "If it's something you can cover in a typical team call, it doesn't belong here." Now that you're all gathered together, use this opportunity to focus on presentations that spark meaningful conversations and inspire collaboration.
#2 - Take a day to get creative. Given that our team and product are both highly technical, a hackathon is the perfect way to tap into everyone’s creativity. We invited each person to bring an idea, and from 9am to 10pm, they had the entire day to bring it to life. Some people teamed up, while others zoned in with their headphones and hacked solo. Some of our non-technical team members even used the time to take an “Intro to Coding” course!
We wrapped up the day with an hour-long demo session, where everyone showcased their finished projects. It was inspiring to see how excited the team was to share their work and celebrate each other’s creativity.
#3 - Give space to openly discuss team culture. Our co-founder Sam sends a culture survey to the team every year, and gives a short presentation on the results to facilitate discussion during the retreat. We paired the presentation with an interactive “2024 retro” this year, and used Parabol to upvote the topics people wanted to discuss.
We used the bulk of the session to talk openly about things we want to change or improve in the way we work. Despite many wonderful aspects of our culture, there are always things that can be tweaked. As the team grows, what might have worked a year ago may not be working for everyone today. Open and frank conversations are critical to ensuring the team continues to work well together. It’s important that everyone, including senior leaders, show an open-ness to hearing what’s not working, and a willingness to adapt their personal preferences for the greater good.
#4 - Book a meeting space with lots of windows. A beautiful location adds to the cost, but pays for itself in terms of inspiration. No one wants to spend their day in a dark and dreary conference room. We went to the extreme - choosing a room with so much natural light that it made using our projector a challenge… Next year, we’ll fix that by renting a large TV, so we can enjoy the sunlight without sacrificing visibility.
#5 Unconferences might work for you, but consider the timing when collecting topics. This year, we tried an unconference style for part of our retreat since we weren’t sure which topics would be most important to everyone. We asked the team to write down topics they wanted to lead, and then we organized the sessions based on their submitted ideas.
In theory, this works, but we discovered a problem. We had asked for topics before having done the strategy session. After the strategy session, it was clear that what we most needed to talk about had changed. Rearranging the unconference schedule that we had put together the night before wasted valuable time.
In the end, it worked out, but be aware that unconferences add extra pressure on both senior leadership and the Ops team. Unlike other activities, unconferences can’t be fully organized before the retreat begins, so flexibility, and quick thinking are key.
#6 Swag bags + welcome reception will set the tone for the rest of the week. Our entire team arrived on Sunday, and were greeted by beautifully prepared swag bags from our Ops team as we stepped into the welcome reception. This reception has become a staple in our retreat agenda, as it’s often the first time of the year many of us see each other in person. With everyone arriving around the same time, the reception sets an inclusive tone for the rest of the week, and offers a perfect chance to reconnect and kick off the retreat on the right foot. It’s a chance to celebrate the past year’s efforts, show gratitude to each other, and remind ourselves why we’re so fortunate to be part of this great team.
#7 Get back to the basics for team activities. People naturally want to unwind and connect, but it helps to provide activities that spark non-work related conversations.
One night, we organized a game night at a local sports bar. We kept it casual with trivia cards, Jenga, and a private room setup with a simulator where people could play soccer, golf, or even zombie dodgeball. It wasn’t anything fancy, but it turned out to be a huge hit! The activities were laid back enough for everyone to join in, while also giving those who preferred to sit back and watch a chance to relax and enjoy the vibe.
#8 Allow a full non-work related team bonding day. As you can probably tell, team cohesion is incredibly important to us. On our final day of the offsite, we partnered with a third party event company to organize a scavenger hunt in La Jolla, complete with lunch integrated into the activity. It was a perfect blend of friendly competition and exploration of the town together. A lively happy hour, followed by a beautiful waterfront dinner as the sun set, provided an unforgettable way to close out a special week.
As we wrapped up our third annual retreat, it was clear just how valuable these in-person gatherings are for a fully remote team like ours. From the creative spark of the hackathon to the friendly competition of the scavenger hunt, every moment reinforced the importance of connection, collaboration, and forward-thinking outside of our usual virtual meetings. These unconference sessions allowed us to focus on critical strategy, sparking innovative ideas, and guiding the future direction of our company.
It’s not just about the work - it’s about fostering relationships, sharing experiences, and making memories that will energize us long after we return to our remote routines. With each offsite, we learn more about what works best for our team, and we’re already excited for next year’s adventure!
If you’re planning your own retreat or offsite, remember to create space for meaningful conversations, strategic thinking, and spontaneous fun. Ultimately, the real impact of these retreats comes from bonds we build, strategies we refine, and the renewed energy to carry back into our everyday work.
By the way, we are hiring! Check out our open roles here.
It’s a huge investment to fly our entire team from the four corners of the earth to get together for our annual offsite. Is it worth it? Undeniably yes, but, a lot of work goes into making sure we get the ROI we hoped for. Our recent team retreat was more than just a rare opportunity for face-to-face collaboration, it became a pivotal moment for aligning on strategy, strengthening team bonds, and sparking fresh ideas that will drive our next chapter. The pressure to deliver is real, but so are the rewards when it all comes together.
With three annual retreats under our belt, we’ve learned some valuable lessons we’ll share in the hope that they might be helpful to others.
This year, we chose Oceanside, California, just north of San Diego, and stayed at The Seabird Resort & Spa - and I can’t recommend this venue enough. It truly exceeded our expectations in every way.
How we spent our time:
Sunday: Arrival and Welcome Reception
Monday: Strategy and Priorities Discussion – Aligning on key goals and unconference in the afternoon
Tuesday: Hackathon – Encouraging creativity through hands-on projects
Wednesday: Team Culture and 2024 Retro – Reflecting on what works and what to improve and unconference in the afternoon
Thursday: Fun Day – Scavenger hunt, relaxing, and bonding as team
Tips:
#1 - Discussions over presentations. Your team likely already has regular meetings to cover status updates, quarterly reviews, and other routine matters—so leave those behind. Save them for your usual remote 9-to-5 schedule. Our unspoken rule was simple: "If it's something you can cover in a typical team call, it doesn't belong here." Now that you're all gathered together, use this opportunity to focus on presentations that spark meaningful conversations and inspire collaboration.
#2 - Take a day to get creative. Given that our team and product are both highly technical, a hackathon is the perfect way to tap into everyone’s creativity. We invited each person to bring an idea, and from 9am to 10pm, they had the entire day to bring it to life. Some people teamed up, while others zoned in with their headphones and hacked solo. Some of our non-technical team members even used the time to take an “Intro to Coding” course!
We wrapped up the day with an hour-long demo session, where everyone showcased their finished projects. It was inspiring to see how excited the team was to share their work and celebrate each other’s creativity.
#3 - Give space to openly discuss team culture. Our co-founder Sam sends a culture survey to the team every year, and gives a short presentation on the results to facilitate discussion during the retreat. We paired the presentation with an interactive “2024 retro” this year, and used Parabol to upvote the topics people wanted to discuss.
We used the bulk of the session to talk openly about things we want to change or improve in the way we work. Despite many wonderful aspects of our culture, there are always things that can be tweaked. As the team grows, what might have worked a year ago may not be working for everyone today. Open and frank conversations are critical to ensuring the team continues to work well together. It’s important that everyone, including senior leaders, show an open-ness to hearing what’s not working, and a willingness to adapt their personal preferences for the greater good.
#4 - Book a meeting space with lots of windows. A beautiful location adds to the cost, but pays for itself in terms of inspiration. No one wants to spend their day in a dark and dreary conference room. We went to the extreme - choosing a room with so much natural light that it made using our projector a challenge… Next year, we’ll fix that by renting a large TV, so we can enjoy the sunlight without sacrificing visibility.
#5 Unconferences might work for you, but consider the timing when collecting topics. This year, we tried an unconference style for part of our retreat since we weren’t sure which topics would be most important to everyone. We asked the team to write down topics they wanted to lead, and then we organized the sessions based on their submitted ideas.
In theory, this works, but we discovered a problem. We had asked for topics before having done the strategy session. After the strategy session, it was clear that what we most needed to talk about had changed. Rearranging the unconference schedule that we had put together the night before wasted valuable time.
In the end, it worked out, but be aware that unconferences add extra pressure on both senior leadership and the Ops team. Unlike other activities, unconferences can’t be fully organized before the retreat begins, so flexibility, and quick thinking are key.
#6 Swag bags + welcome reception will set the tone for the rest of the week. Our entire team arrived on Sunday, and were greeted by beautifully prepared swag bags from our Ops team as we stepped into the welcome reception. This reception has become a staple in our retreat agenda, as it’s often the first time of the year many of us see each other in person. With everyone arriving around the same time, the reception sets an inclusive tone for the rest of the week, and offers a perfect chance to reconnect and kick off the retreat on the right foot. It’s a chance to celebrate the past year’s efforts, show gratitude to each other, and remind ourselves why we’re so fortunate to be part of this great team.
#7 Get back to the basics for team activities. People naturally want to unwind and connect, but it helps to provide activities that spark non-work related conversations.
One night, we organized a game night at a local sports bar. We kept it casual with trivia cards, Jenga, and a private room setup with a simulator where people could play soccer, golf, or even zombie dodgeball. It wasn’t anything fancy, but it turned out to be a huge hit! The activities were laid back enough for everyone to join in, while also giving those who preferred to sit back and watch a chance to relax and enjoy the vibe.
#8 Allow a full non-work related team bonding day. As you can probably tell, team cohesion is incredibly important to us. On our final day of the offsite, we partnered with a third party event company to organize a scavenger hunt in La Jolla, complete with lunch integrated into the activity. It was a perfect blend of friendly competition and exploration of the town together. A lively happy hour, followed by a beautiful waterfront dinner as the sun set, provided an unforgettable way to close out a special week.
As we wrapped up our third annual retreat, it was clear just how valuable these in-person gatherings are for a fully remote team like ours. From the creative spark of the hackathon to the friendly competition of the scavenger hunt, every moment reinforced the importance of connection, collaboration, and forward-thinking outside of our usual virtual meetings. These unconference sessions allowed us to focus on critical strategy, sparking innovative ideas, and guiding the future direction of our company.
It’s not just about the work - it’s about fostering relationships, sharing experiences, and making memories that will energize us long after we return to our remote routines. With each offsite, we learn more about what works best for our team, and we’re already excited for next year’s adventure!
If you’re planning your own retreat or offsite, remember to create space for meaningful conversations, strategic thinking, and spontaneous fun. Ultimately, the real impact of these retreats comes from bonds we build, strategies we refine, and the renewed energy to carry back into our everyday work.
By the way, we are hiring! Check out our open roles here.
