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Corporate offsites can be a welcomed (or dreaded) part of any job. You might be getting an all-expenses-paid vacation, but it’s still with your boss.
Given the large expense that goes into hosting a sales offsite—B2B event planning company BoomPop estimates that an average team retreat costs $2,000 to $3,000 per attendee—it’s important that companies and their employees get the most out of the experience.
Whether you like them or not, sales offsites—which includes events like sales kickoffs, quarterly meetings, or team-building exercises—have increased in frequency in recent years. According to a report from travel management company Emburse, the average number of annual corporate offsites has increased from 2.4 in 2019 to 2.6 in 2024.
BoomPop’s chief executive officer, Healey Cypher, told Revenue Brew there are five key things that sales leaders should keep in mind in order to host a successful offsite.
Don’t plan by the calendar, plan by the moment
While most sales kickoffs are held in January or February, Cypher suggests that companies should host offsites around important moments at other points in the year.
“We found that the best sales teams have critical moments, and they plan around that,” he said. “It could be a product launch, or could be a strategy shifting, or even a rallying cry—like we’re missing numbers; we need to get morale back on. There’s something about that that has a lot of benefits.”
Always start with the after
The goals of any offsite, such as new product training or onboarding a new strategy, should be both top of mind and clearly defined at the beginning of the planning process to make sure it is achieved.
“The alternative is, I’m just throwing a party,” Cypher said. “It’s to get people to have fun, which is definitely important for a lot of reasons, but start planning your [sales kickoff] with the after. What’s the goal of it? Make sure you know it.”
Meetings don’t build teams, experiences do
While the takeaways and learnings are an important part of any sales offsite, team building and fun activities are just as crucial in creating an immersive and engaging experience for employees.
“What I found is it’s really easy, especially for a sales kickoff, to have people sit back into chairs and they’re consuming content like a classroom,” Cypher said. “We found the best thing is you need to get people up, moving and doing things. That’s what they’re going to remember.”
Cypher cited an offsite BoomPop helped host for German manufacturing company Tesa in Savannah, Georgia, where the company planned a scavenger hunt in the city.
“That’s all they talked about,” he said.
Cypher explained these types of experiences help boost morale and collaboration.
“Perhaps importantly, [sales offsites offer] a renewed motivation to hit their goals,” he said. “Sales teams can have different stuff they focus on, different product lines, and there is a renewed sense of cross-collaboration, cross-understanding of the larger context in the business. A lot of our clients believe that the best businesses push decision-making and context down to the very, very bottom rung of the organization because it’s very hard to make decisions if you don’t have the broader context. Often [salespeople] leave being not just motivated and not just [cross-collaborating] but having a very clear sense of what it is they need to do to be successful at that business, and they want to do it now.”
Recognition fuels results
It’s no surprise that positive reinforcement yields positive outcomes. A sales offsite should be used to further this to keep morale high.
“The best salespeople are wired for achievement,” Cypher said. “You celebrate their wins, both formally and informally, and you reinforce the performance culture you have in the sales organization.”
Own the impact, not the logistics
Cypher explained BoomPop exists because of this tenet. Planning a sales offsite can become hard to manage when considering travel, lodging, meals, activities, etc. Cypher stressed outsourcing that planning is key, so that sales leaders can remain focused on the goals, content, and presentations.
“You should be thinking about hitting quota and incentivization and the right mix—all that sort of stuff,” he said. “Instead, you’re like, ‘oh shit, we didn’t book the hot air balloon! What are we going to do?’ You shouldn’t be doing that. If you’re focused on the storytelling of that event, the strategy, and the connection, and you leave the hotel contracts and the shuttle schedules to someone else—that is critical.”