In our September webinar, nearly half of the attendees said the started planning their yearly sales kickoff in Q3. Another quarter won’t start until the middle of Q4. Whether it’s a matter of procrastination or prioritization, we hear that sales leaders tend to put off planning their biggest sales gathering of the year, starting well beyond the point they should.

The truth is that to achieve the SKO of your dreams, you can’t afford to wait. If you’re struggling to start, try this step-by-step, repeatable process used by SailPoint’s enablement leaders, Global Revenue Enablement Associate Manager Robin Barde, and Global Revenue Enablement Manager Meredith Linze. For more, watch the full on-demand episode of Leading The Challenger Sale.

What makes a great kickoff?

Maybe your first reaction is “really great swag and a 1:2 person-to-happy-hour ratio.” You might not be wrong, but a truly functional sales kickoff must also achieve several goals. 

  • First, it needs to set the tone for the year. Sellers need inspiration after a tough quarter closing their pipelines, especially following a year of economic uncertainty. Identify how your team needs to feel when they leave the SKO and use it to guide your planning. 
  • Second, think about how you’ll align sellers and revenue teams with the organization’s goals and values. Your organization must speak with one voice at your SKO, emphasizing what’s important at an organizational level as well as what’s at stake. 
  • Next, recognize that while the SKO energizes sellers, that energy needs to be pointed in the right direction. Sellers should leave the event able to clearly articulate their focus for the year to come. 
  • Finally, yes — it should be fun!

Choose Your Theme

What ideas are you kicking around for your SKO theme? Since you’ll build the rest of your event (ahem—swag! Workshops! Breakout sessions!) around this idea, conversations about the theme should start early and can begin as soon as the end of your previous SKO. Grab a whiteboard, block an hour on your calendar, and make a list of stakeholders whose input you’ll need. 


  • Feedback from your planning team
  • Insights from leadership
  • Insights from your previous SKO’s attendees 

Once you’ve aligned on an overall theme, consider a tagline. SailPoint’s 2023 SKO, “Sail Forward,” featured the tagline “Faster. Tougher. Together.” Executive speakers and keynote presenters drew this thread through their presentations and even included it in company meetings throughout the year.

Define Your Goals

With a solid theme in place, it’s time to outline your SKO goals. If the theme drives the overall feel of and messaging around your event, then goals help dictate the content. 

Remember that different teams might have different goals. Your enablement team and sales leaders might want to emphasize certain tactical skills or revisit your recent sales training program. Leadership might want to lay out their strategic vision for the year. Encouraging all your stakeholders to articulate their vision can help you settle on the right goals for your event. Each SKO session should map back to those strategic goals. Your follow-ups — training, sales meetings, even your company’s all-hands — in the year ahead should do the same.

It’s all about giving reps what they need to walk away from the SKO feeling confident and excited about meeting their objectives. 

Drive Interactivity

You know that your kickoff will be exciting, that your theme will serve as a rallying cry, and that your speakers will reinforce your goals. But how can you keep your sellers engaged, especially with a full schedule and so many things pulling at their attention? 

Our guests recommended tapping into interactivity, particularly through gamification. That might be as simple as asking them to participate in a photo competition. For our SailPoint guests, selecting an adorable mascot with layers of meaning helped give sellers a focal point. The SailPoint team also used an app to get real-time feedback from sellers. Those tuning in remotely could connect with a live broadcast feed between sessions.  

Plan to incorporate activities that unlock your sellers’ competitive instincts. Adding fun competitions and building opportunities for engagement will keep their attention and increase stickiness, too. 

Plan for Reinforcement

On that note, our SailPoint guests’ final suggestion was this: the SKO is just the beginning of a year-long enablement journey. If you don’t follow up with reinforcement, you risk sellers losing nearly three-quarters of everything they learned within days

To make sure your SKO efforts aren’t wasted, you’ll want to create a reinforcement plan that pulls your theme and goals through to next December. This might look like: 

  • Equipping frontline managers with a “meeting in a box” to help them revisit SKO learnings with their direct reports
  • Planning to add any materials to your learning management or sales enablement platform after the event
  • Creating a feedback loop for participants to submit questions and identify areas where further training is needed 

Effective SKO Planning Starts Now

We hope these steps from expert SKO planners jumpstart your planning journey. No matter where you are in the process, the time to start is now. For more inspiration, including SailPoint’s speaker preparation process and a template you can use to prep your speakers, watch the on-demand webinar “Practical Tips for an Unforgettable SKO.” 

Want to watch the next Leading the Challenger Sale webinar live? Sign up for the series here.

Challenger, Inc.

Challenger is the global leader in training, technology, and consulting to win today’s complex sale. Our sales transformation and training programs are supported by ongoing research and backed by our best-selling books, The Challenger Sale, The Challenger Customer, and The Effortless Experience.