5 Strategies for a Kick-Ass Sales Kickoff

Another sales kickoff season is upon us. While many sales teams plan to hold in-person kickoffs, organizers must still accommodate a hybrid sales team. Sales teams are dispersed around the globe, and remote work is here to stay.

I know—not what you want to hear. Thinking about holding another virtual sales kickoff probably fills you with dread, picturing a computer screen filled with tiny faces and knowing many of your reps are slowly drifting into boredom.

It doesn’t have to be that way, though. With the help of technology, you can transform a dreary hybrid sales kickoff into a dynamic one.

Here are five tactics to help you have a sales kickoff that motivates and informs your sellers, recognizes their achievements, connects team members, and makes some fun.

5 Strategies to Transform Your Sales Kickoff

1. Build Excitement and Expectations for Your Kickoff

Whether your sales kickoff is in-person, virtual, or a mix of both, you want to create excitement around the event and set expectations. Ways to do that: share a welcome video by sales leadership, send teaser emails highlighting what’s to come, and introduce external speakers.

Example: Send a video clue each day leading up to the event to get people guessing what the sales kickoff theme is. Get creative and use costumes, music, and props.

2. Use Effective Learning and Training Strategies

Boredom sets in when you have to listen to an instructor talk for an hour about a subject. And when it’s a videoconference, it’s even worse. Not only that, but research shows that retention goes down as the volume of information goes up. To keep your sales reps engaged and ensure they retain what they learn, have shorter face-to-face trainings. Share recordings of longer sessions and let reps watch on their own before the meeting. Doing so not only allows reps to watch when and where they want, but they can also rewatch them if they miss anything. Then, break your team into small groups to discuss and apply what was taught and/or invite outside experts to do a live Q&A.

Example: Make the most of your time together—whether in person or virtual—by sharing knowledge ahead of the kickoff and using face time for Q&As, role-plays, discussion, practice, and reinforcement.

Make the most of your time together—whether in person or virtual—by sharing knowledge ahead of the sales kickoff.

3. Invite Your Sales Reps to Help Plan and Present Sessions

Developing all the content for a sales kickoff is a huge task. Rather than doing it all yourself, crowdsource the effort and invite your sales reps to be part of the process. They can provide insight into top issues and challenges, plus they can create content that can also be used later to reinforce learning or as part of your training and onboarding. This works on two levels: sales reps love talking about themselves and their wins, and junior sellers love hearing real-world examples from their peers.

Example: Ask your top-performing reps to share their biggest deals. They can discuss how they started the sales conversation, what the discovery process was like, obstacles they experienced, how they overcame those obstacles, and the result. Record their presentation and break it into smaller videos to include in your sales training program or coaching sessions.

4. Make Your Sales Kickoff More Than Just Learning

The proverb “All work and no play makes Jack a dull boy” applies to sales kickoffs as much as it does to individuals. To prevent your kickoff from being dull, whether your event is in-person or virtual, be sure to include breaks in between learning sessions and add interactive elements. Ways to do that: include polls and quizzes, hold contests and give prizes to the winners, and present awards for sellers’ achievements.

Example: Give your sales reps their moment in the sun by recognizing top performers, new hires, work anniversaries, and other achievements. You might consider doing superlatives (flashback to your high school yearbook): Most Likely to Always be Closing, Best Team Player, Best Coach, Most Improved, and Most Likely to Make it Rain

5. Provide a Collaborative Space to Share Content

With sales kickoffs, organizations send lots of emails about the event and inevitably someone will accidentally delete an email or misplace the attachment that was included. You may also have some reps who are unable to attend the event and must watch recordings of the presentation. The best way to handle those communications, videos, and any content shared as part of the kickoff is to create a dedicated, collaborative place to store it. This reduces confusion about where to find things and allows sales reps to share comments and feedback.

Example: Create a digital room within your sales enablement platform to store all announcements, pre-event videos, recordings of live meeting sessions, day-of activities, and post-event information. Allow your reps to post questions and feedback on each and address those comments during the live event or as part of your post-event exercises.

Bonus Tip: Do Something Fun with Your Team

Be sure to include something fun as part of your sales kickoff strategy. Give your reps an opportunity to get to know one another and bond over something not related to work. It can be as simple as dinner at a restaurant or an evening of karaoke. If you have regional teams, they can have their own luncheon or dinner. And if a virtual setting is preferred, virtual tastings (chocolate, wine, cheese, etc.) are popular options.

Prepare Now for Your Sales Kickoff

Watch Annual Sales Kickoff Meetings: Your Early Preparation Checklist to get advice on how to plan a successful sales kickoff and get a handy checklist to help you prepare.