Mastering Corporate Retreats for Startups: Part I - Advocating & Planning

January 29, 2024
Milana Martinovic

Milana has been involved in hospitality and events her entire career. Her journey in operations, support and distributed work started with Airbnb and continues among other startups in the ever evolving tech space. The two worlds connected 6 years ago when Milana got involved with building one of the frontrunners in the company retreat market in the evolving space of remote work. OnsiteHub was created as a culmination of 20 years experience in hospitality, tourism and startups to help distributed teams get together and enhance culture and connection.

Heading 1

Heading 2

Heading 3

Heading 4

Heading 5
Heading 6

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur.

Block quote

Ordered list

  1. Item 1
  2. Item 2
  3. Item 3

Unordered list

  • Item A
  • Item B
  • Item C

Text link

Bold text




As a corporate event manager working for a startup, I was told coming in that I would be wearing many hats. These included working with a PR agency, creating their first event strategy from the ground up, and organizing an offsite retreat for a remote team of sixty people.

“Ok sure!”, I said, just happy to land the job after a full-time parenting career hiatus. 

After onboarding was complete, I had only six months to organize the offsite. And despite the fact that this event was part of my job duties, I received pushback from the C-suite, who had to justify the event to their investors. They believed an offsite would be a waste of time as they were primarily concerned with cost savings and sales. Here’s how I proceeded to present my case, and garner buy-on for our retreat.

Our Remote Team Was Craving In-Person Connection and Communication 

As an advocate of remote work environments (for many reasons), I also understand how lonely and difficult it can be. I quickly observed how some of my team members were siloed, and many of them didn’t feel comfortable writing to a colleague they’d never met before in person. Knowing how crucial a team retreat can be in boosting company morale and encouraging teamwork, I was determined to create an event that would foster these connections in person. 

Here’s What I Proposed

Employees are your best investment. Without them, there would be no company, revenue, or profit, so hosting a team retreat could be the essential driver to keeping them on and keeping them loyal.

 I wanted a week. I stressed  the importance of a longer time together since it would just be once a year, and two of the days would be spent traveling. 

I wanted a larger budget. I pointed out that when compared to what we would be spending to rent an office, 100K is a drop in the bucket. 

In the end, I did get the full five days of the team retreat, plus one day for just the management to meet. And I was able to pull it all off under the 100K allotted budget. It was a major success, rising high above all expectations, and creating all around team motivation. 

The 5 Benefits of In-Person Retreats I Highlighted When Advocating for Our Company Retreat

1. Strengthening Virtual Bonds & Alleviating Remote Isolation

In a fully remote work setting, face-to-face interactions are rare. Having the opportunity to connect on a personal level, enhances trust and communication, resulting in improved collaboration during virtual work. 

TIP: Use statistics! Investors love numbers. Though the advantages of an offsite are difficult to quantify, it’s still worthwhile to include. Here is a resource with team building statistics, as well as a quote from Annie Dean from the Atlassian on her company’s in person meetups here.

2. Fostering Innovation & Creativity Through New Perspectives

One distinct advantage of remote work, particularly when teams are composed of global talent, is the opportunity for cultural diversity and new perspectives. At my previous employer, management was primarily located in one area, where they could frequently interact in person. What they missed, however, was utilizing the untapped potential of ideas and perspectives from the rest of the global team. Coming together in person creates opportunities for distributed teams to exchange new ideas, share cultural perspectives, and tap into a greater sense of collective innovation and creativity. 

TIP: Emphasize the value of your global team! This can give you a critical edge over non-remote working companies, but the only way to explore this advantage is to explore it at an in-person offsite.  

3. Boosting Remote Productivity

The C-Suite was concerned about the potential loss of work hours during the retreat. Admittedly, I didn’t have an answer at first as I had not taken this factor into consideration. I suggest proactively emphasizing both the long term benefits around productivity (post retreat) as well as providing a clear plan to address the shift in work hours during the retreat, including any customer communication needed. A well-executed retreat can boost remote team productivity by reinvigorating team members and reinforcing their commitment to the organization's goals.

TIP: Provide testimony! Ask colleagues if they would be willing to share why they feel a team retreat would help them with their productivity.

4. Attracting Remote Talent and Retaining Team Members

Prospective remote employees are drawn to organizations that prioritize their well-being and professional development, including opportunities for in-person interaction.

As a way to capitalize on this opportunity, I proposed hiring a videographer for our trip to document the experience.The video that we created was essential for employer branding. People get so excited when they see there are  opportunities to meet in person in a new place! It can offset the loneliness that often comes with remote culture. Emphasize  how offering team retreats as part of your remote company culture can be a powerful recruiting tool. 

TIP: Research the competition and find similar companies who have utilized company retreats! Seeing competitors who are attracting top talent through company culture perks like in-person retreats can inspire stakeholders to jump on board. 

5. Dedicated Strategic Planning and Goal Setting

Use the retreat as an opportunity to stress the importance of strategic planning and goal setting, even in a remote context. A retreat can provide a dedicated space for remote teams to align with the company's objectives, fostering a stronger sense of purpose and connection to the organization.

TIP: Create an example schedule! Show that you have thought about the time each team can dedicate to meeting and planning their goals together. This will showcase that you understand that a team retreat is not just a party. 

Some Final Things to Consider

Remember, you know that a team retreat is beneficial for your remote company, but sometimes it requires highlighting some of the tangible benefits. When it comes to your proposal, gather quotes from hotels and potential activities and be sure to include photos. It’s also helpful to offer a range of options and variations you can present if needed, such as suggesting a more budget-friendly location or smaller team divisions. Once you have the C-Suite on board, you can start planning the fun stuff, which I’ll be exploring in the next article.

In the world of fully remote work, team retreats are an invaluable investment in the future success of your organization. As an event manager, when advocating for a team retreat, arm yourself with the compelling benefits discussed above to make a persuasive case to the C-Suite, investors, and stakeholders. It may seem like a lot of work, but the result will be worth it.

If you are an in-house corporate event manager that needs a little assistance, consider working with a dedicated company retreat company like OnsiteHub, whose mission it is to create meaningful retreat experiences across the best locations in Europe that foster unity, enhance communication, and spark innovation. 

Having help from an outside company who specializes in planning team retreats can allow you to focus solely on creating an impactful event strategy that will have an undeniably positive impact on your company. 

Good luck!


Unforgettable retreats. Stronger teams.

Let us do the hard work for you. Bring your team together with ease and enjoy an unforgettable European company retreat experience.

Let’s get started