Dockwa x Brightwild: Planning Dockwa’s Company Retreat
“Creating memorable experiences is what I am passionate about. I felt like all of the experience I have been gaining over the last 15+ years in this industry was finally all coming to fruition with this opportunity.” - Cheyne, Brightwild
Founder & CEO of Brightwild, Billy Spottswood, brought a challenge to our operations team: Plan a large team retreat for Dockwa [an online tool that connects marinas and boaters] at a cluster of our properties and give them a memorable experience.
To give background, too, Dockwa and their team have not been collectively together in person since COVID, so it was important for our team to be able to create a space where they could reconnect, and for some, even connect for the first time.
We wanted to give you a peek behind the curtain at what that planning process looked like here at Brightwild. Enter Cheyne, our Lead Guest Experience Manager who also dabbles with putting on large group events at several of our properties, including Curry Mansion Inn and Key Haven Estates.
Q: Did you have any prior experience planning events like this?
A: I had never planned anything on this scale before. However, I did have one big notch on my belt from a wedding weekend I put together at the Curry Mansion for a couple. I never could have pulled it off alone; I had help from so many people from both inside and outside the company. That weekend was near perfection. So I was confident that we could pull it off again and then some.
Q: Give us a rundown on what was brought to you at the very start of the partnership with Dockwa.
A: Dan [Dan Garcia, Sr. Director of Operations] and I weren't sure what to expect at first. Billy asked us one day to create a pitch deck for Dockwa. Our first conversation with Dockwa was mostly us sharing information about the houses and some talk about potential dining and activities. Instead of Dockwa JUST using our houses, I thought, ‘Why not provide them with the full Brightwild experience and go above and beyond for this reservation.’
I started brainstorming different group activities that would be feasible for 50+ people. I reached out to my contacts and learned how to use Pitch on the fly [a presentation software.] I created our first Pitch deck and stacked it to the brim with activity options for each day of their trip. Knowing they would likely cut out most of it, I wanted to be over prepared and overdeliver.
We got Rick Haskins [Principal Broker at Brightwild] involved because we knew he would be a key asset in making this thing shine. He joined us for our second meeting, and we showed them [Dockwa’s leadership] how badass this event was all going to be.
After that, things started getting more personal. We linked up with Dockwa via Slack and worked out all of the finer details. I made one final Pitch deck laying everything out for their team, and by that time, other people in our company were starting to catch the scent of what we had been cooking in the kitchen.
I gave Elizabeth [Brightwild Art Director] the first round of the deck that I had thrown together (which, may I note, was much better than my high school powerpoints.) She made it even more badass and up to Brightwild’s brand standards–This was the cherry on top. Dockwa was blown away in our final meeting.
This thing was officially happening and I was beyond stoked.
Q: Lay out what actually ended up taking place
A: In no particular order, Dockwa partook in: A private chef dinner with local musician, Jason Lamson, fishing & other activities throughout Key West, cooking up their catches at Hogfish Grill, taking Brightwild Adventures boats out to the sandbar, a pop-up event at KAMP, a riveting bar crawl on Duval, and so much good connection time for the whole team.
Dockwa x Brightwild: Planning Dockwa’s Company Retreat
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“Creating memorable experiences is what I am passionate about. I felt like all of the experience I have been gaining over the last 15+ years in this industry was finally all coming to fruition with this opportunity.” - Cheyne, Brightwild
Founder & CEO of Brightwild, Billy Spottswood, brought a challenge to our operations team: Plan a large team retreat for Dockwa [an online tool that connects marinas and boaters] at a cluster of our properties and give them a memorable experience.
To give background, too, Dockwa and their team have not been collectively together in person since COVID, so it was important for our team to be able to create a space where they could reconnect, and for some, even connect for the first time.
We wanted to give you a peek behind the curtain at what that planning process looked like here at Brightwild. Enter Cheyne, our Lead Guest Experience Manager who also dabbles with putting on large group events at several of our properties, including Curry Mansion Inn and Key Haven Estates.
Q: Did you have any prior experience planning events like this?
A: I had never planned anything on this scale before. However, I did have one big notch on my belt from a wedding weekend I put together at the Curry Mansion for a couple. I never could have pulled it off alone; I had help from so many people from both inside and outside the company. That weekend was near perfection. So I was confident that we could pull it off again and then some.
Q: Give us a rundown on what was brought to you at the very start of the partnership with Dockwa.
A: Dan [Dan Garcia, Sr. Director of Operations] and I weren't sure what to expect at first. Billy asked us one day to create a pitch deck for Dockwa. Our first conversation with Dockwa was mostly us sharing information about the houses and some talk about potential dining and activities. Instead of Dockwa JUST using our houses, I thought, ‘Why not provide them with the full Brightwild experience and go above and beyond for this reservation.’
I started brainstorming different group activities that would be feasible for 50+ people. I reached out to my contacts and learned how to use Pitch on the fly [a presentation software.] I created our first Pitch deck and stacked it to the brim with activity options for each day of their trip. Knowing they would likely cut out most of it, I wanted to be over prepared and overdeliver.
We got Rick Haskins [Principal Broker at Brightwild] involved because we knew he would be a key asset in making this thing shine. He joined us for our second meeting, and we showed them [Dockwa’s leadership] how badass this event was all going to be.
After that, things started getting more personal. We linked up with Dockwa via Slack and worked out all of the finer details. I made one final Pitch deck laying everything out for their team, and by that time, other people in our company were starting to catch the scent of what we had been cooking in the kitchen.
I gave Elizabeth [Brightwild Art Director] the first round of the deck that I had thrown together (which, may I note, was much better than my high school powerpoints.) She made it even more badass and up to Brightwild’s brand standards–This was the cherry on top. Dockwa was blown away in our final meeting.
This thing was officially happening and I was beyond stoked.
Q: Lay out what actually ended up taking place
A: In no particular order, Dockwa partook in: A private chef dinner with local musician, Jason Lamson, fishing & other activities throughout Key West, cooking up their catches at Hogfish Grill, taking Brightwild Adventures boats out to the sandbar, a pop-up event at KAMP, a riveting bar crawl on Duval, and so much good connection time for the whole team.
.png)
“Creating memorable experiences is what I am passionate about. I felt like all of the experience I have been gaining over the last 15+ years in this industry was finally all coming to fruition with this opportunity.” - Cheyne, Brightwild
Founder & CEO of Brightwild, Billy Spottswood, brought a challenge to our operations team: Plan a large team retreat for Dockwa [an online tool that connects marinas and boaters] at a cluster of our properties and give them a memorable experience.
To give background, too, Dockwa and their team have not been collectively together in person since COVID, so it was important for our team to be able to create a space where they could reconnect, and for some, even connect for the first time.
We wanted to give you a peek behind the curtain at what that planning process looked like here at Brightwild. Enter Cheyne, our Lead Guest Experience Manager who also dabbles with putting on large group events at several of our properties, including Curry Mansion Inn and Key Haven Estates.
Q: Did you have any prior experience planning events like this?
A: I had never planned anything on this scale before. However, I did have one big notch on my belt from a wedding weekend I put together at the Curry Mansion for a couple. I never could have pulled it off alone; I had help from so many people from both inside and outside the company. That weekend was near perfection. So I was confident that we could pull it off again and then some.
Q: Give us a rundown on what was brought to you at the very start of the partnership with Dockwa.
A: Dan [Dan Garcia, Sr. Director of Operations] and I weren't sure what to expect at first. Billy asked us one day to create a pitch deck for Dockwa. Our first conversation with Dockwa was mostly us sharing information about the houses and some talk about potential dining and activities. Instead of Dockwa JUST using our houses, I thought, ‘Why not provide them with the full Brightwild experience and go above and beyond for this reservation.’
I started brainstorming different group activities that would be feasible for 50+ people. I reached out to my contacts and learned how to use Pitch on the fly [a presentation software.] I created our first Pitch deck and stacked it to the brim with activity options for each day of their trip. Knowing they would likely cut out most of it, I wanted to be over prepared and overdeliver.
We got Rick Haskins [Principal Broker at Brightwild] involved because we knew he would be a key asset in making this thing shine. He joined us for our second meeting, and we showed them [Dockwa’s leadership] how badass this event was all going to be.
After that, things started getting more personal. We linked up with Dockwa via Slack and worked out all of the finer details. I made one final Pitch deck laying everything out for their team, and by that time, other people in our company were starting to catch the scent of what we had been cooking in the kitchen.
I gave Elizabeth [Brightwild Art Director] the first round of the deck that I had thrown together (which, may I note, was much better than my high school powerpoints.) She made it even more badass and up to Brightwild’s brand standards–This was the cherry on top. Dockwa was blown away in our final meeting.
This thing was officially happening and I was beyond stoked.
Q: Lay out what actually ended up taking place
A: In no particular order, Dockwa partook in: A private chef dinner with local musician, Jason Lamson, fishing & other activities throughout Key West, cooking up their catches at Hogfish Grill, taking Brightwild Adventures boats out to the sandbar, a pop-up event at KAMP, a riveting bar crawl on Duval, and so much good connection time for the whole team.
Q: What parts of this event were easiest to plan? What was the most difficult?
A: The easiest part of the retreat to plan was definitely the accommodations. We knew the whole team was all staying at Key Haven, and that nothing else in our portfolio was going to ‘wow’ them like those houses would. Needless to say, they were living in luxury.
The most difficult part was planning the opening night private chef event. Nothing made me more nervous than this. This was the first day all of these people had been together in person since the lockdown in 2020. Some, for the first time ever. So many factors were involved and could go wrong. We had to go back and forth with the caterer a few times in order to find the right menu and price. We also had multiple conversations about which house was the right fit to host this event at. It ended up going off without a hitch and was certainly a highlight of the retreat.
Q: What were the most rewarding parts of this entire process for you?
A: The end result is always the most rewarding for me. People are my passion. I truly love creating lasting memories that people will carry with them for years to come. Hearing all of the compliments and seeing all of the glowing reviews after the retreat made me giddy.
I remember laying on my bed after everything was said and done, knowing that we, as a team, had absolutely crushed every aspect of this event. I was kicking the air like an excited child that got exactly what he wanted for Christmas.
Q: What did you learn in planning an event like this?
A: I would overplan and overdeliver on the pitch again. I think giving the guests ample options to choose from is key to finding what is right for a specific group. Not everyone likes paella.
Q: What stressed you out? What brought you joy?
A: Transportation by far stressed me out the most for this retreat. I never ever could have pulled it off without Rick, Parker, James, and Matt [Brightwild employees.]
We would have shown the Presidential Motorcade how it’s done had they been around to witness our impeccable punctuality and color coordination.
Seeing the faces of everyone having a wonderful time brought me immense joy. You could really feel the camaraderie watching Dockwa’s team reconnect after years of not having been together in person. It just feels special to have been a part of making that happen.
Q: How did you ensure that the event catered to the diverse needs and preferences of attendees?
A: Constant communication and deliberation with Dockwa themselves.
Working with KK, Steven, and Mike was a pleasure. Their input and insight into the events and their team was invaluable. We were regularly bouncing ideas off each other and made sure to tailor every event to accommodate their team’s specific needs.
Q: Reflecting on the entire experience, what advice would you give to someone planning a similar event in the future?
A: Don’t be afraid to ask for help and request outside opinions. So many factors go into planning something of this scale and one person doesn't have all of the best ideas. Collaborate with your team members, vendors, and the guests. Teamwork makes the dream work.
Q: What feedback did you receive from attendees or leadership after the event?
A: Thankfully, the vast majority of feedback we received was glowingly positive. There is definitely more we can do for future groups in regard to tailoring specific needs at the homes themselves. The reviews speak for themselves though, we knocked it out of the park.
Q: What parts of this event were easiest to plan? What was the most difficult?
A: The easiest part of the retreat to plan was definitely the accommodations. We knew the whole team was all staying at Key Haven, and that nothing else in our portfolio was going to ‘wow’ them like those houses would. Needless to say, they were living in luxury.
The most difficult part was planning the opening night private chef event. Nothing made me more nervous than this. This was the first day all of these people had been together in person since the lockdown in 2020. Some, for the first time ever. So many factors were involved and could go wrong. We had to go back and forth with the caterer a few times in order to find the right menu and price. We also had multiple conversations about which house was the right fit to host this event at. It ended up going off without a hitch and was certainly a highlight of the retreat.
Q: What were the most rewarding parts of this entire process for you?
A: The end result is always the most rewarding for me. People are my passion. I truly love creating lasting memories that people will carry with them for years to come. Hearing all of the compliments and seeing all of the glowing reviews after the retreat made me giddy.
I remember laying on my bed after everything was said and done, knowing that we, as a team, had absolutely crushed every aspect of this event. I was kicking the air like an excited child that got exactly what he wanted for Christmas.
Q: What did you learn in planning an event like this?
A: I would overplan and overdeliver on the pitch again. I think giving the guests ample options to choose from is key to finding what is right for a specific group. Not everyone likes paella.
Q: What stressed you out? What brought you joy?
A: Transportation by far stressed me out the most for this retreat. I never ever could have pulled it off without Rick, Parker, James, and Matt [Brightwild employees.]
We would have shown the Presidential Motorcade how it’s done had they been around to witness our impeccable punctuality and color coordination.
Seeing the faces of everyone having a wonderful time brought me immense joy. You could really feel the camaraderie watching Dockwa’s team reconnect after years of not having been together in person. It just feels special to have been a part of making that happen.
Q: How did you ensure that the event catered to the diverse needs and preferences of attendees?
A: Constant communication and deliberation with Dockwa themselves.
Working with KK, Steven, and Mike was a pleasure. Their input and insight into the events and their team was invaluable. We were regularly bouncing ideas off each other and made sure to tailor every event to accommodate their team’s specific needs.
Q: Reflecting on the entire experience, what advice would you give to someone planning a similar event in the future?
A: Don’t be afraid to ask for help and request outside opinions. So many factors go into planning something of this scale and one person doesn't have all of the best ideas. Collaborate with your team members, vendors, and the guests. Teamwork makes the dream work.
Q: What feedback did you receive from attendees or leadership after the event?
A: Thankfully, the vast majority of feedback we received was glowingly positive. There is definitely more we can do for future groups in regard to tailoring specific needs at the homes themselves. The reviews speak for themselves though, we knocked it out of the park.
Dockwa x Brightwild: Planning Dockwa’s Company Retreat
“Creating memorable experiences is what I am passionate about. I felt like all of the experience I have been gaining over the last 15+ years in this industry was finally all coming to fruition with this opportunity.” - Cheyne, Brightwild
Founder & CEO of Brightwild, Billy Spottswood, brought a challenge to our operations team: Plan a large team retreat for Dockwa [an online tool that connects marinas and boaters] at a cluster of our properties and give them a memorable experience.
To give background, too, Dockwa and their team have not been collectively together in person since COVID, so it was important for our team to be able to create a space where they could reconnect, and for some, even connect for the first time.
We wanted to give you a peek behind the curtain at what that planning process looked like here at Brightwild. Enter Cheyne, our Lead Guest Experience Manager who also dabbles with putting on large group events at several of our properties, including Curry Mansion Inn and Key Haven Estates.
Q: Did you have any prior experience planning events like this?
A: I had never planned anything on this scale before. However, I did have one big notch on my belt from a wedding weekend I put together at the Curry Mansion for a couple. I never could have pulled it off alone; I had help from so many people from both inside and outside the company. That weekend was near perfection. So I was confident that we could pull it off again and then some.
Q: Give us a rundown on what was brought to you at the very start of the partnership with Dockwa.
A: Dan [Dan Garcia, Sr. Director of Operations] and I weren't sure what to expect at first. Billy asked us one day to create a pitch deck for Dockwa. Our first conversation with Dockwa was mostly us sharing information about the houses and some talk about potential dining and activities. Instead of Dockwa JUST using our houses, I thought, ‘Why not provide them with the full Brightwild experience and go above and beyond for this reservation.’
I started brainstorming different group activities that would be feasible for 50+ people. I reached out to my contacts and learned how to use Pitch on the fly [a presentation software.] I created our first Pitch deck and stacked it to the brim with activity options for each day of their trip. Knowing they would likely cut out most of it, I wanted to be over prepared and overdeliver.
We got Rick Haskins [Principal Broker at Brightwild] involved because we knew he would be a key asset in making this thing shine. He joined us for our second meeting, and we showed them [Dockwa’s leadership] how badass this event was all going to be.
After that, things started getting more personal. We linked up with Dockwa via Slack and worked out all of the finer details. I made one final Pitch deck laying everything out for their team, and by that time, other people in our company were starting to catch the scent of what we had been cooking in the kitchen.
I gave Elizabeth [Brightwild Art Director] the first round of the deck that I had thrown together (which, may I note, was much better than my high school powerpoints.) She made it even more badass and up to Brightwild’s brand standards–This was the cherry on top. Dockwa was blown away in our final meeting.
This thing was officially happening and I was beyond stoked.
Q: Lay out what actually ended up taking place
A: In no particular order, Dockwa partook in: A private chef dinner with local musician, Jason Lamson, fishing & other activities throughout Key West, cooking up their catches at Hogfish Grill, taking Brightwild Adventures boats out to the sandbar, a pop-up event at KAMP, a riveting bar crawl on Duval, and so much good connection time for the whole team.
Q: What parts of this event were easiest to plan? What was the most difficult?
A: The easiest part of the retreat to plan was definitely the accommodations. We knew the whole team was all staying at Key Haven, and that nothing else in our portfolio was going to ‘wow’ them like those houses would. Needless to say, they were living in luxury.
The most difficult part was planning the opening night private chef event. Nothing made me more nervous than this. This was the first day all of these people had been together in person since the lockdown in 2020. Some, for the first time ever. So many factors were involved and could go wrong. We had to go back and forth with the caterer a few times in order to find the right menu and price. We also had multiple conversations about which house was the right fit to host this event at. It ended up going off without a hitch and was certainly a highlight of the retreat.
Q: What were the most rewarding parts of this entire process for you?
A: The end result is always the most rewarding for me. People are my passion. I truly love creating lasting memories that people will carry with them for years to come. Hearing all of the compliments and seeing all of the glowing reviews after the retreat made me giddy.
I remember laying on my bed after everything was said and done, knowing that we, as a team, had absolutely crushed every aspect of this event. I was kicking the air like an excited child that got exactly what he wanted for Christmas.
Q: What did you learn in planning an event like this?
A: I would overplan and overdeliver on the pitch again. I think giving the guests ample options to choose from is key to finding what is right for a specific group. Not everyone likes paella.
Q: What stressed you out? What brought you joy?
A: Transportation by far stressed me out the most for this retreat. I never ever could have pulled it off without Rick, Parker, James, and Matt [Brightwild employees.]
We would have shown the Presidential Motorcade how it’s done had they been around to witness our impeccable punctuality and color coordination.
Seeing the faces of everyone having a wonderful time brought me immense joy. You could really feel the camaraderie watching Dockwa’s team reconnect after years of not having been together in person. It just feels special to have been a part of making that happen.
Q: How did you ensure that the event catered to the diverse needs and preferences of attendees?
A: Constant communication and deliberation with Dockwa themselves.
Working with KK, Steven, and Mike was a pleasure. Their input and insight into the events and their team was invaluable. We were regularly bouncing ideas off each other and made sure to tailor every event to accommodate their team’s specific needs.
Q: Reflecting on the entire experience, what advice would you give to someone planning a similar event in the future?
A: Don’t be afraid to ask for help and request outside opinions. So many factors go into planning something of this scale and one person doesn't have all of the best ideas. Collaborate with your team members, vendors, and the guests. Teamwork makes the dream work.
Q: What feedback did you receive from attendees or leadership after the event?
A: Thankfully, the vast majority of feedback we received was glowingly positive. There is definitely more we can do for future groups in regard to tailoring specific needs at the homes themselves. The reviews speak for themselves though, we knocked it out of the park.
