Maximize Your ROI from Your Sales Kickoff: Best Practices for a Winning SKO 2025

Sales Kickoffs (SKOs) are major investments that set the tone for the year, align vision and strategy, and ultimately get everyone motivated and moving in the same direction. But how do you ensure that your SKO is an unforgettable event that drives real ROI?

2025 Sales Kickoff Best Practices

Align Vision and Strategies

Your SKO should be aligned with your company's vision and 2025 annual goals and strategies. This will bring everyone together around the big picture and help them focus on what really matters for the year ahead.

"The most important thing you can do is the prep work. Make sure that your key topics match up with the company's top priorities."

-Dan Conway | CEO | 2Win!

A successful SKO doesn't start the day of the event—it starts long before, with precision planning. Every part of your SKO needs to be linked to the bigger picture. You are setting your team up to walk away feeling clear on expectations and confident in their ability to contribute to the organization's goals.

Balancing Content and Fun

SKOs need to strike a balance between delivering valuable content and keeping things fun and engaging. If you have amazing content, but no one is paying attention to your presentation, what's the point? The audience will not walk away with anything that sticks.

Incorporating Storytelling

Connect and Inspire

Storytelling makes your content relatable and memorable. When teams can connect emotionally with a message, they’re more likely to internalize it and recall it later.

For instance, if you’re presenting on the importance of consistency in the buying process, try using an analogy: “Imagine buying the same pair of jeans from the same brand, only to find they fit differently each time. It’s frustrating and makes you question the brand’s quality. The sales process should be no different—consistency builds trust and makes the journey smooth for the customer.” Stories bring messaging to life, making it easier for your team to connect the dots and take action.

Reinforce Learning and Keep Your Audience Engaged

It's not that you have to reinvent the wheel regarding SKOs, but it is an opportunity to think outside the box and incorporate engaging activities that reinforce learning.

• Sales Jeopardy: Create categories around product knowledge, sales techniques, or the company's goals.

• Family Feud: Encourage friendly competition between the different teams– AEs vs SEs.

• [Company's Name] Got Talent: This event allows participants to showcase their skills and receive feedback from a panel of judges.

These are fun ways to bring energy and camaraderie to your Sales Kickoff and reinforce learning in a memorable way.

SKO Crimes

Things to Avoid

Even the best SKOs can fall into common traps that impact the effectiveness of the event. Here are the top three crimes we see at Sales Kickoffs.

1. Information Overload: If everything is important, then nothing is important. Pick a few key topics and focus on making those stick.

2. Unclear Messaging: With everything that is happening at an SKO, it is easy for your message to fall to the waste side if it's not clearly defined.

3. Lack of Clear Action Items: Every session should conclude with actionable takeaways. Without these, your SKO risks becoming an experience that fades quickly once the event wraps up.

Get the Most from Your SKO with 2Win!

We understand that an effective SKO is more than just presentations and handouts. Our training approach makes complex sales techniques clear, interactive, and actionable. With masterclass sessions, storytelling workshops, and activity-driven learning, your team leaves the SKO with confidence, skills, and the motivation to drive results all year.

Ready to make this year’s SKO your best yet? Partner with 2Win and turn your investment into measurable results that stick.