11 Tips to Sustain Your Sales Kickoff Event in 2024

Studies show that companies spend approximately $2,000 per sales rep at an annual sales kickoff meeting (SKO) in the form of meeting space, event technology, airfare, transportation, hotel accommodations, catering, swag, speaker fees, and entertainment. For this investment, sales leaders expect to strengthen culture, improve team camaraderie, increase understanding of company goals, and even usher in necessary reformations. But are these expectations truly met, or is the enthusiasm and learning generated at an SKO meeting a flash in the pan?

According to McKinsey, sales leaders are seeking to build capabilities that are well suited to today’s often remote, highly digital paths to purchase, which require the day-to-day application of new learning and skills. Successful organizations are introducing rigid performance management and a systematic approach to skills development, often as weekly steering cadences and targeted coaching.

In other words, planning a memorable, informative SKO at the beginning of the fiscal year is insufficient. Sales leaders must also plan ongoing reinforcement of the teambuilding and training that took place during the SKO so desired behaviors are not only introduced but also internalized.

Here are 11 tips for sustaining SKO momentum throughout 2024:

1. Set the stage.

During your sales kickoff event, make it clear that the event is the beginning of a year-long initiative and that a series of events and activities will follow. Design your sales kickoff agenda to guide participants on high-level themes and clarify how they will learn more throughout the fiscal year. Every participant should leave your SKO event with the understanding that the SKO’s theme and framework for learning will be a consistent part of the culture going forward.

2. Make SKO content available year-round.

Sales reps should be able to access SKO presentations and content on demand, whether the need is a “just-in-time” guide to a CRM function or a sales playbook for a given persona. If you have the talent and technology, insert bookmarks into videos for easy content retrieval. Also, extend the half-life of your SKO content by creating video clips or shareable quotes from customer or executive presentations for sales and marketing teams to use after the event. And remember that in addition to supporting the sales team with quick access to necessary resources, the event can be made available to new hires to accelerate onboarding!

Note: If your sales kickoff is in a hybrid or virtual format, consider an annual license for your event technology to create an “evergreen” virtual SKO event where the event and the content are accessible year-round from any location. One of the benefits of doing so is that you will be able to collect data and gain insights into views and downloads, so you’ll know which content resonates and can approach planning for future SKOs more informed.

3. Develop a post-kickoff training program at the same time you plan your SKO.

Your SKO should be the beginning of a learning journey for your sales reps, not the end. Create a comprehensive training program that builds on the content offered at your sales kickoff. Programs can be self-paced and asynchronous, which allows reps to participate virtually and move at their pace on their schedule. Alternately, programs can be synchronous, where the entire team gathers to progress through training milestones. Successful companies often incorporate certifications, gamification, and financial incentives in the post-SKO learning journey to create accountability and encourage engagement. They also mix content formats like in-person, podcasts, and video to appeal to different learning styles.

Note: Make sure sales leaders have the right technology to identify learning gaps and track progress through your post-kickoff program. For example, if reps are expected to complete an e-learning course, make sure the technology doesn’t just send sales leaders a notification of completion but provides measurable ways to assess reps’ strengths and weaknesses and gain insights into training performance.    

4. Provide routine coaching.

McKinsey reports that top-quartile B2B sales teams provide “business-specific guidance to focus and direct seller activities” in daily or weekly huddles. Guidance provided during these huddles can take many forms, such as simulations of customer conversations, collaborative problem-solving, and discussions about the best ways to support sales activities. But regardless of the nature of the guidance, what’s important is that sales reps can now become exponentially effective after the SKO.

Note: If your sales huddles are taking place virtually, a good idea is to occasionally host a “manager swap,” where a sales leader from a different territory or product line runs the huddle. This is a great way to eliminate silos within the sales organization as well as gain more objective feedback since leaders from other teams are likely less emotional about the deals in the pipeline.

5. Hold routine “sales enablement” calls.

Rather than build a complete arsenal of technology, content, and information for your SKO, leave yourself room to pivot as the market changes and instead view your SKO as the beginning of a “sales enablement” series. Following your sales kickoff, schedule a “sales enablement” call every other week, during which sales and sales support teams, including marketing, product marketing, solutions consultants, sales operations, and customer success, communicate and work together to enable the sales team to respond to market fluctuations. For example, product marketing can introduce new marketing assets. Solutions consultants can review a “closed won” story in a new vertical or market. Sales operations can provide training on a new CRM feature. By routinely connecting cross-departmental teams, you can foster camaraderie and collaboration akin to an SKO, align messaging, processes, and priorities, and even accelerate pipeline velocity.

6. Communicate often.

Create vehicles for sales leaders, reps, and sales support teams to share tips and provide insights to sustain information-sharing and collaboration beyond the SKO. This can be a dedicated Slack channel, Teams group, or biweekly newsletter.

Note: If you publish a newsletter, make it interactive. Insert videos or a poll or ask a trivia question. Like an SKO event, you want your audience to engage, not just listen. Also, to enable your sales teams, highlight any content in the newsletter that can be shared externally and provide social media copy, UTMs, etc. to make sharing easy. Finally, be sure to include industry news and competitive intelligence. These will evolve in real time after your SKO, and because sales teams are busy, it can be challenging to stay informed. Use your newsletter to directly feed sales reps the news and research they need to perform better.

7. Create a throughline.

Define a theme for your SKO, and then reinforce this theme in everything you do after the event, such as training programs, sales huddles, and newsletters. Incorporating a throughline will make your post-SKO events and activities more memorable, and by tying everything back to the sales kickoff, you’re consistently emphasizing what’s important to the organization. When choosing a theme, make sure it reflects your organization's goals. The theme should be something every team, not just sales, can embrace over the course of a year and easily serve as a focal point for all post-SKO events and activities.     

Note: Be careful not to drone on about your theme! The key isn’t repetition; it’s discussion.

8. Involve cross-departmental leaders in SKO planning.

By involving cross-departmental leaders in your SKO event, you’ll enrich the quality of the SKO content and set the right tone for working across functions throughout the year. Encourage forward-thinking during your planning sessions by discussing the key objectives you want to introduce at the event and how you envision the growth trajectory following the sales kickoff. 

9. Make time to connect.

Be sure your SKO agenda includes time for team building and networking. The connections participants make during your SKO meeting will help improve communication, idea exchange, and peer coaching throughout the year. Team building and networking can take the form of cross-departmental working sessions, healthy competitions, team dinners, or happy hours. Remember that regardless of your team building and networking format, the goal should be to align the employees better personally and professionally.  

Note: If you have a content-rich agenda and are worried you don’t have enough time for team building and networking, try to identify topics that can be shared with the participants before the sales kickoff meeting, such as organizational changes, territory assignments, and commission plans.

10. Gamify your SKO.

Experiential learning is a great way to boost engagement and retention during an SKO, so identify opportunities to gamify the experience, such as using quizzes and trivia contests or negotiation or role-playing challenges. Then, periodically launch the same games as part of your post-SKO programming. This will allow you to re-capture some of the fun of your sales kickoff, assess how much information was retained, and reinforce knowledge.

11. Track performance metrics.

Establish performance metrics at your SKO and track and measure these throughout the year. Celebrate achievements during sales huddles and sales enablement calls and in your sales newsletters to recognize high-performers, reignite the enthusiasm generated at your SKO, and create a culture of accountability. Tracking progress toward goals will also help sales leaders validate the success of the SKO and post-event programming and lay the foundation for continuous improvement.

Note: Don’t just focus on the big metrics, like revenue. Celebrate the use of a new sales play or email outreach template. Recognize the sales rep who posted an article on LinkedIn or had the most content “shares.” Call attention to early adopters of the content and practices you share throughout your sales kickoff and post-event programming to encourage others to follow the example.     

An SKO is just the beginning.

Sales kickoff events are great opportunities to reinforce company culture, create cohesion, and develop sales reps’ skills. To sustain the momentum generated at your SKO, however, developing a post-event program that includes content, training, communication, and performance measurement is crucial.

For advice on how to host an SKO that starts your sales trajectory off right, contact 6Connex today.