If you fail to plan, you can plan to fail…so the saying goes. We’ve all likely been a part of an event or meeting where you’re going through the experience and the internal dialogue in your head is, “Seriously, this is a mess, what are we even doing here, help, please let this be over soon.”
To the contrary, I’m sure everyone can recall attending a very well planned event or meeting where there’s no need for a negative internal dialogue, you just enjoy the moment and say, “Wow, this is awesome, well done everyone.” My favorite SKO Guru I've ever worked with had a perfect track record of planning and executing many successful sales kickoff events (save for one questionable location that I’ll leave unnamed).
A sales kickoff (SKO) is perhaps the most important event of the year for a sales organization. It’s a time to celebrate wins and reward hard work. It’s a special occasion to re-energize and refresh your team. It’s an opportunity to train your team and introduce new themes and methodologies. But most importantly, the SKO is your moment to orient your sales team for the upcoming year.
If you pull off your SKO well, the impact on your sales organization will last for the rest of the year—you’ll remind them of why their work is important and why they love doing it.
But impact doesn’t happen by accident. It requires forethought and intentionality.
Without this planning, your SKO could end up being little more than a party, or a series of mind-numbing lectures. Neither of these would provide your reps with a sense of purpose. Even worse, a failed SKO can actually damage team morale, decrease motivation, and actively harm your culture. Ideally, you want your sales reps leaving your SKO looking forward to the next one and energized for the year to come, not relieved that it’s over and burnt out.
It’s imperative to get this right. So how do you do that?
In this article, we’ll walk you through what it takes to run a sales kickoff that sets your team up for a successful year.
- Sales kickoff basics
- How to plan and prep for your sales kickoff
- Best practices for your sales kickoff
Sales kickoff basics
Before we jump into planning and running a sales kickoff, let’s briefly go over the basics: what an SKO is, when and where it occurs, and what it can accomplish for your team.
What is an SKO?
A sales kickoff is usually a multi-day company event that brings together the entire sales department to celebrate wins from the previous year and set the course for the coming year. Management and in some cases supporting teams like marketing, product, and customer service join the sales department to participate in a series of keynote presentations, tactical training sessions, and team activities.
An SKO has the potential to be a mountaintop experience that inspires people to move toward a common objective, with enough emotional and motivational staying power to fuel their pursuit of that objective until the next SKO. Sales kickoffs can boost morale, grow skill sets, reinforce company culture, and align your whole organization.
When should you have your sales kickoff?
Sales kickoffs typically occur annually, though some organizations choose to host them more frequently, sometimes corresponding with projects or product launches.
The traditional choice has been to host SKOs in January, aligning with the start of Q1. However, many companies have recently started pushing their SKOs further back in the quarter to February or even March. December often represents the hardest and most stressful time of the year for sales reps, who may end the year feeling burnt out. Postponing the SKO gives employees a chance to breathe and recover first, allowing them to more fully absorb the impact of the event.
Delaying until February or March also reduces the potential overlap between the kickoff and other organization-wide planning, so you can devote your full attention to each activity and ensure your SKO builds upon your organizational goals for the year.
Of course there are no fixed rules for when you can host a sales kickoff, so it ultimately comes down to whatever time makes the most sense for the specific needs of your organization.
Where should you have your SKO?
Traditionally, sales kickoffs have been in-person events hosted at offsite locations—often in well-known cities that double as tourist destinations, such as Las Vegas, Palm Springs, or Nashville.
Making a destination event out of an SKO can add a bit of fun and excitement, while also providing plenty of nearby opportunities for team activities. But this isn’t necessarily a requirement. Organizations can also choose to host their SKOs closer to home, reducing travel costs and jet lag (especially if the organization is smaller and/or localized to one area).
Additionally, many organizations switched to doing remote SKOs during the pandemic, and some have chosen to keep them that way moving forward. However, in an age where remote and hybrid work have become so commonplace, hosting an in-person SKO may be more valuable than ever, as it provides team members who barely see each other outside of Zoom calls with a rare chance for in-person interaction.
High-level SKO goals and expectations
The number one goal that you should have for any sales kickoff you run is to make a positive impact. Let’s unpack what exactly that means.
Your sales kickoff should be motivational. An SKO should be something that sales employees look forward to year round, pushing them to do their best in anticipation of the event. And while there, it should further reinforce their drive and passion for what they do.
Sales reps should leave feeling refreshed and re-energized for the upcoming sales period. You want them to be glad to be a part of the team and excited about the future, believing they’ve continued to make the right investment in staying with your sales organization.
And your sales kickoff should unite your team around a common goal. You need to impart a sense of purpose, something to rally behind and work toward until the next SKO. Ideally, you should have a single company objective: one big thing that you want everyone to take away from the event.
Beyond these overarching goals, you may have additional elements you wish to communicate during the SKO. For example, you may need to explain a change in team structure, introduce a new sales strategy, or train your team on a particular sales tactic.
These can all be valuable things to include in a sales kickoff, but it’s crucial that you present them in a manner that doesn’t distract from the “one big thing” you need your team to take away from the event. Everything else should be crafted to complement and support that singular aim.
How to plan and prep for your sales kickoff
Planning ahead ensures that all the details of your SKO are accounted for and nothing is left to chance. It involves gathering input from relevant stakeholders, deciding what you’re going to focus on, selecting a theme, and outlining a detailed agenda.
Assemble your team
To run a successful sales kickoff, you don’t want to go it alone. You should start bringing in feedback and perspectives from a wide range of stakeholders well before you get into the specifics of the SKO itself.
That starts with the chief revenue officer and/or the senior vice president of sales. Theirs are the opinions you’ll find most valuable for informing and shaping the sales kickoff.
Next, you’ll want to collaborate with marketing leadership and the sales team managers. The managers in particular are best suited to understand the issues sales reps are facing, their personal interests and preferences, and what it will take to craft an SKO that will motivate and drive them.
You’ll also need to be in communication with the C-level executives throughout the process. They probably won’t be directly collaborating with you on planning the event, but you’ll need to be sure that they’re aware of your plans and that they’ve given their approval for the direction you intend to head.
Determine your “one big thing”
With your team of stakeholders assembled, it’s time to reach out to learn what they hope to get out of the sales kickoff. Start by asking each of them what they would choose if there was only one thing they could guarantee to accomplish from the event.
You’re likely to get a variety of responses from the different roles you talk to. For example, they may want to see the team doing deeper discovery on phone calls, increase sales of a certain product, hit quotas more consistently, improve employee morale, or better compete with a specific competitor.
Once you have all of that feedback, you can start working to distill it into a single overarching goal that can accommodate all the small specific goals that each stakeholder brought to the table. Then that “one big thing” is what will direct the rest of your planning.
Decide on an SKO theme
Choosing a theme is an essential part of planning a sales kickoff, but depending on where you look for advice, you’ll tend to find one of two seemingly opposed directions you can head with it.
In one corner, you’ll find the serious straightforward business-centric sales kickoff themes. These are things like beating a certain competitor, focusing on the customer, or collaborating with team members.
And in the other corner, you’ll find lighthearted, playful, and (at times) eye-rolling sales kickoff themes that almost seem better suited to a birthday party than a corporate event—themes that parody blockbuster films, popular game franchises, television genres, or the destination itself.
So which kind of theme should you choose?
As always, it depends on the specifics of your organization as well as your sales reps’ interests and personalities. Look to the sales team managers in particular to determine what kinds of themes would resonate best.
And whichever type of theme you select, the most important part will be tying it directly to the “one big thing” you identified to drive the SKO. Something kitschy can be fine, but only if you’re able to make it relevant to what you’re hoping to get out of the event.
For example, based on the feedback you received from the stakeholders, you might have decided that leveling up the team’s performance is your “one big thing” to aim for. “Leveling up” works great as a theme in itself if you’re going for a more business centric approach.
But if you want to wrap that up in a more fun and lighthearted theme, you might go with a popular game franchise, say, Pokémon—emphasizing how the stages of evolution the monsters go through parallels the “leveling up” you want the sales team to experience.
The sky's the limit, so long as the theme supports your “one big thing” rather than distracting from it.
Create a detailed SKO agenda
When planning your agenda, try to adopt a “less is more” mentality. You don’t want to pack the schedule so full that you burn out your reps. Be sure to schedule plenty of free time, and mix up the business elements with fun activities.
For the first and last days, you’ll have to factor in the flights to and from the event. Account for possible travel delays, and then give your team plenty of time to move through baggage claims, settle into their hotel rooms, and get refreshed before starting any events.
You’ll likely only do one keynote that first afternoon—a relatively light presentation that simply welcomes everyone to the SKO, sets expectations, introduces the theme, and explains the agenda for the coming days. Then treat your team to dinner, and call it a day.
For the second day, you really get into the meat of the sales kickoff. Start with a nutritious breakfast to help your team focus, and then move into a more thorough keynote presentation. You might go over the previous year or sales period, praising the team for the highlights while also covering things to work on. You’ll also want to reinforce the theme you introduced previously.
Then you might do a breakout training session, focusing on a specific skill or sales strategy. Follow that up with lunch. And perhaps that afternoon you could take everyone out for a fun team-building activity.
The third day will follow a similar format to the second, as will any additional days before returning home. You might end it with an awards dinner, providing special recognition to those who have done exceptionally well, and encouraging performance for the next sales period.
The final day will be fairly short, accounting for return travel. Provide breakfast in the morning before they leave, thank your team for all their hard work, and wish them well for the coming year.
Here’s a sample schedule for what a four-day (including travel) sales kickoff might look like:
- Day 1
- Incoming flight
- Keynote
- Dinner
- Day 2
- Breakfast
- Keynote
- Training session
- Lunch
- Personal time
- Fun activity
- Dinner
- Day 3
- Breakfast
- Keynote
- Fun activity
- Lunch
- Training session
- Personal time
- Training session
- Awards dinner
- Day 4
- Breakfast & sendoff
- Return flight
Best practices for your sales kickoff
Our team at Performio has put together (and attended) countless SKOs, and we’ve talked with many other sales teams about their SKO experiences. Based on what we’ve learned, these are the tips you’ll want to keep in mind in order to create an SKO that will be engaging to everyone and accomplish its goals.
Stay focused on your singular objective
Remember that the most fundamental goal of a sales kickoff is to make a positive impact on your sales team. And the best way to do that is by distilling everything you want to communicate into a single clear message for them to take away from the event that will motivate them for the coming sales period.
Figure out your “one big thing” early on in the planning process and incorporate it into everything you do. The theme, the schedule, the training sessions—it should all tie back to that key purpose.
Find the right balance between learning and fun
At the end of the day, a sales kickoff is a corporate event that is intended to drive performance for your sales organization. But it should also be something enjoyable that sales reps look forward to throughout the year. And mixing up business with fun is a great way to help your employees stay focused throughout the event and be able to absorb the things you want them to learn.
You don’t want to go too far in the direction of fun, such that you lose focus on your “one big thing” and turn the SKO into a party. But you do want to sprinkle enough fun throughout to keep your reps engaged. Keep it lighthearted, tie fun elements into learning activities, and break up the training sessions with a few recreational activities.
Avoid overpacking the schedule
Remember that less is more for an SKO. Stick to what you need to accomplish, and don’t try to fit in too many extra events just to fill the schedule. Make sure that every event feels meaningful, whether the goal is learning or community building.
An eight to five day event that is wall to wall with training sessions and death by powerpoint is a surefire way to induce burnout. And once that happens, the rest is a loss. Your employees won’t be retaining much of anything if the schedule is packed too full.
It’s much better to space out learning events, provide plenty of breaks and free time, and sprinkle in fun activities. You should be thinking about the minimal amount you can do for the maximum output.
Factor inclusivity into everything you plan
Reps from different backgrounds bring varying viewpoints to the table and enrich the team as a whole. But unfortunately, many sales kickoffs fail to account for the diversity found in their sales teams. If you aren’t being intentional about inclusivity, then it can be easy for the ethos and activities of an SKO to cater toward a single perspective. This is an especially easy mistake to make if your sales leaders are all of the same gender, the same ethnicity, or from similar backgrounds.
This doesn’t mean you should start slapping rainbows on everything or offer a tokenized “women’s activity” like a spa date. But it does mean you should take time to think through the activities you plan, making sure that whatever you select will be applicable to everyone—or that you offer multiple options with something for everyone to enjoy. Not everyone plays golf, or enjoys hiking, or wants to watch the opera—and not everyone can, either. Be sure to also factor accessibility needs into your planning!
One of the best ways to stay on top of inclusivity is to talk with the sales team managers. They’ll be able to provide you with information about all the members of their team, what they enjoy, what kinds of activities they’d be up for doing, and what elements to steer clear of. Being intentional about inclusivity is one the best things you can do to build a team that people love, where everyone feels welcome.
Plan to follow up on your SKO
Once the event is over, everyone has returned home, and business resumes as normal, you’ll want to intentionally follow up on your sales kickoff to ensure sales reps have retained what they learned and are putting their training into practice.
This can include a thank-you note sent out about a week after the SKO, reminding the team of the highlights from the event, reiterating the “one thing” you want them to take away, and expressing gratitude for their participation.
Additionally, you should coordinate with sales team managers and sales coaches to have them continue developing the theme from the SKO as they work with their sales reps moving forward throughout the sales period.
Keep your team on track year-round with Performio
Sales kickoffs happen a few times a year at most, but for every day in-between, you need to be motivating your team and helping them work toward their goals. That means you’ll need sales data to understand how well they’re doing and to keep them on track.
With Performio, our world-class software does all the heavy lifting for you, meticulously tracking everything from the performance of individual sales reps to the team as a whole, no matter how your teams are composed. Our performance and reporting dashboards simplify complex data, pulling out crucial insights to show you exactly what you need to know.
Additionally, each of your reps will be able to see their own progress toward quotas and goals, as well as how much they can expect to earn—meaning they no longer have to resort to “shadow accounting” to track these things for themselves, and can instead stay focused on making sales.
Want to see what Performio can do for your organization? Request a demo today.