How to prep for your successful 2023 sales kickoff

AdobeStock_280996343There’s nothing like encouraging your sales team to aim high, getting ready for the new year and  having a sales kickoff (SKO) to get things moving. 

The aim for the SKO is to prepare, educate and re-energize sales reps as they enter the new year. But SKO’s need to take into account any new changes, trends, competitors and products in the marketplace – so no year is quite the same. 

How can you ensure your SKO sets up sellers for the utmost success? Let’s dig into it.


What is a sales kickoff (SKO)?

Successful sales teams plan and prepare for the year ahead. A great way of doing this is by having an SKO yearly, usually at the very beginning of the year. In the best case, it will be a face-to-face event or a hybrid one, but in this day and age, more and more SKOs happen virtually. Even though we understand the need for online events, there’s nothing that beats in-person when it comes to team bonding! 

At the SKO, you want the team to bond and share initiatives across departments, but even more so to train and coach reps on the skills they need to succeed. One way to do that is through engaging, motivational and educational content. 


3 things you need for a successful SKO 

Without these three elements your SKO might be stale and less successful. You need a strong mix of each.


  1. 1. Motivate reps to feel inspired

You want reps to feel motivated and ready to take on new challenges and find new opportunities – so you need a healthy dose of: inspiration! You can use creative delivery like gamification and competitions, but the important takeaway is that reps feel energized and dedicated to the new strategies for 2023. 

Your company may want to use the SKO to communicate new internal changes. Share a new piece of technology or a new sales organizational structure, new product updates, sales strategies or whatever is coming this year. Always highlight why they’re important for your company and how they will benefit everyone. We encourage you to keep it engaging via creative means: use video, have breakout sessions where reps can play games and have fun with competitions along the way! 


  1. 2. Educate reps to feel more confident 

Education will be the bulk of your SKO. Make the most of this time by prioritizing training and coaching for the most important things you want to communicate. Remember, people can only retain so much information at one time, and usually learn by doing and applying the knowledge in real context, not listening.

You can tailor content for reps based on specific regions, roles or customer segments, and get even more granular in sessions. If you have a new sales enablement tool, try focusing on one new feature or functionality, like how to pitch content from within the platform. Then you won’t overwhelm reps, and you could show it with a fun demo so they can try it out for themselves. 


  1. 3. Celebrate wins and look ahead 

Often, an SKO ends with a big celebration of wins, top performers and some fun before the grind begins again. You’ll also want to include fun team-building activities to maximize bonding opportunities. 

Often, sales organizations will do the usual happy-hour or a dinner – but why not branch out next year? You could hire a magician, a motivational guest speaker or offer creative activities like improv classes. Then, you can guarantee a memorable event! 


What to do before, during and after your sales kick off 

In an ideal world, the SKO is not just a one-time event which reps easily forget about. Encourage reps to participate in momentum-building before, during and after the event. 




  • Align with stakeholders: Ensure that your agenda aligns with the priorities of the key leadership. Don’t waste your time on topics that don’t have buy-in (even if you are expecting it later). Before your event, get clear on what challenges your reps are having, where and when they occur, and why. Know the specific sales skill, product or coaching that the SKO will offer to help reps overcome these challenges.
  • Optimize your SKO sales play: Create a SKO sales play kit and give it to reps as a single source of truth. Tells them what to know, say and do to prepare for the event.
  • Incentivize participation: Encourage your team to get excited ahead of the event, as you need their buy-in for it to be a success. It’s not a given. Pitch it to them and tell them what benefits they’ll get out of it (and no, it’s not just the happy hour!). Build excitement by building in games and competitions with cool prizes. 
  • Set an intention: Any successful event or meeting can benefit from setting an intention at the beginning and then checking off that you have followed through on it. Ask both sales managers and reps what they want from their SKO experience. Tailoring your event to their needs and expectations will ensure they’re excited to attend — and stay engaged during.



We’re emphasizing the fun element here, since usually SKOs are known for being long days with boring lectures. That doesn’t have to be the case! The best SKO should keep your sales team engaged from the moment they arrive to the second they leave. How do you achieve this? 


  • Prioritize what to teach: Try not to cram all training and teaching in one go. Scatter it throughout the day, and try to prioritize the key 3-5 takeaways. Make it fun and engaging. If you have lots of new elements or new products to train, offer deep-dive sessions after the SKO and let the SKO be an introduction.
  • Make the learning fun: Have a quiz at the end of the day, use gamification elements and award fun prizes.
  • Prep the learning: Have the sales reps prepare beforehand with pre-read content. Then use the SKO sessions for discussions and Q&A, rather than have your team sit through boring presentations.
  • Discuss wins and fails: You can discuss what worked and what didn’t last year, or brainstorm and have reps share ideas on how to improve sales processes for the upcoming year.
  • Teach to learn: One of the best ways to reinforce knowledge is to teach it to someone else. So why not let reps who already know best practices share their knowledge and success stories with other reps?
  • Role play to reinforce learning: Let reps learn on a deeper level and retain their knowledge better via role-playing sessions or other in-person practice techniques.
  • Shake it off: Sitting in a chair all day is not only unhealthy but also extremely dull, especially when it comes to passive listening. Keep things fun and engaging by offering yoga, stretching sessions or a fun break-out game of soccer (or whichever game works). You might even want to include a putting range, a basketball hoop or a ping pong table that reps can use in breaks. Also, be open to sessions outside if it’s nicer weather, or moving a discussion session to a restaurant or cafe. 




  • Follow up: Ensure that you follow up on any new knowledge or training needed. Reinforce skills with ongoing sales training and coaching, ideally delivered via your sales enablement platform. Always prepare managers with helpful guidelines on how to coach for new skills.
  • Buy the tools your team needs for success: Ensure your team has all the best tools at their fingertips. This includes an advanced CRM system, workflow automation process and sales enablement tools to achieve all of next year’s goals. 
  • Offer just-in-time learning: To optimize learning opportunities and leverage learning when reps need it, offer just-in-time learning via your sales enablement platform so reps can access training when they need it.


3 best practices for online SKOs 

  1. 1. Make it interactive 

Don’t be boring – make it interactive. To make the most of it, have reps complete pre-work beforehand so they’re already clued up on the facts. Then you can use sessions to be more interactive and discussion-based. Use virtual breakout rooms to let the team share takeaways and learn from each other, mimicking face-to-face exchanges.


  1. 2. Short and sweet

If you have a virtual SKO,  keep sessions shorter to avoid fatigue. Keep presentations short and easily digestible; break longer sessions into bite-sized chunks and include lots of shorter breaks. Try to keep most sessions to under half an hour, then add 5-10 minute breaks in between sessions and a one-hour lunch. 


  1. 3. Use specific team-bonding online techniques

You can’t expect the same bonding experience online as you would in-person. You can still have a virtual happy hour, but you’ll get the best bonding experience if you have smaller breakout rooms and lots of icebreaker fun and unexpected questions. Use online trivia games such as and similar, or include cooking events to keep it fun and engaging along the way. If your organization is more informal, you can even use cheekier card games such as Cards Against Humanity and other Q&A games for people to get to know each other.  

We hope you have found this useful to help plan your next SKO. Now, go and enjoy getting ready for 2023, and discover more on how to help your sellers.

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