Virtual SKO Planning: Educate, Motivate, Entertain!


November and December are always a frantic time for sales leaders: closing out the current year while simultaneously preparing for the upcoming year. There are a hundred things to consider, from redesigning compensation plans to setting quotas and capacity planning. And then there is the daunting challenge of hosting a sales kickoff. Each year, sales leaders develop multi-day in-person events to train and update their sales teams on new techniques/processes/tools, celebrate the successes of the past year, and energize the team for the year to come. This year they will need to do all of that – and virtually. 

Making a sales kick-off virtual isn’t just doing last year’s event over Zoom; it’s fundamentally different. And if you plan ahead and follow these tips, it can be even better than those in-person events. On a recent webinar with many heads of sales in our portfolio, we discussed the opportunities and challenges of a virtual SKO. One of the biggest opportunities is the ability to extend the SKO into a full company kick-off. For a minimal additional cost, everyone in the firm can hear the vision of the CEO and sales leaders, get insight into the sales strategy, and most importantly, understand precisely their role in helping sales achieve its goals. Another key benefit of the virtual event is the flexibility it offers when booking guest speakers: By avoiding the logistics of flying guest speakers to events, you can engage someone from anywhere in the world, or engage someone previously outside of your budget range.

Virtual SKOs require a different approach than in-person events

To help you plan yours,  here are 5 key considerations and a few useful tips from our portfolio and from Jacco van der Kooij, the CEO of Winning by Design, a sales enablement consultant.

  1. Drive an impactful engagement: It’s easy to multitask during a virtual event, so you have to create something that is compelling and holds the audience’s attention.  
    • Hype it up – leverage short-burst videos to create breaks in the presentations and mix in music to change the mood.
    • Keep the sessions short and succinct – approximately 45 minutes.
    • Spread the sessions over a few days (with no more than a 4-hour session block) rather than holding an 8-hour-long marathon event.
    • Key Tip: Leverage music, Kahoot, Mentimeter to shake things up.
  2. Plan and Practice: We’ve all had those moments where Zoom doesn’t work right, or a presenter forgets that they’re on mute. In a normal meeting, it’s mildly annoying; in an SKO with 100+ people on the call, it’s disastrous. 
    • Double the amount of time needed to create the event.
    • Test your technology with each speaker, and always have a backup plan.
    • Practice the transitions to create smooth and natural handoffs.
    • Record sessions in advance, and stick to the timing.
    • Key Tip: Have one dedicated moderator and one dedicated tech support person.
  3. Teach them something new: This is true even in physical events, and in a virtual one, you can’t keep your audience captive.
    • Use breakout rooms to engage smaller groups.
    • Assign pre-work for attendees.
    • Train the trainers in advance. Make certain that they can drive impactful sessions.
    • Key Tip: Ask your reps in advance for feedback on what they want to hear or learn about. Also, at the end of a segment, ask one member of the audience to summarize their key takeaways. Then, have them select the next person to do the same.
  4. Let them catch up with their peers: One of the best parts of SKO is being able to share best practices and war stories with peers. Make your virtual event memorable by giving them this capability when they weren’t expecting it.
    • Plan specific times for catch-up sessions.
    • Create coffee chats or happy hours with random assignment of attendees to breakout rooms.
    • Key Tip: Create wedding table assignments for breakout rooms to ensure mixing of teams.
  5. Keep it going after the event: Because a virtual event costs a fraction of a physical event, you can hold follow-on events throughout the year.
    • Create a reinforcement program to drive home key learnings from the SKO.
    • Host a mid-year event. Things changing rapidly; a mid-year meeting allows you to course-correct.
    • Key Tip: Use Slack channels or Teams chats to collect ideas live during the sessions and to communicate with the attendees throughout the year.

The shift from physical event to virtual may seem daunting, but if you keep the above considerations in mind, you will create a game-changing event. Take advantage of technology and the reduced cost to expand the reach of your event and energize the whole organization, not just sales. But most important, remember that during your event, you should Educate, Motivate, and Entertain.  

President's Club in the Age of COVID-19

  • Travis Kassay, Executive Vice President, Sales & CS COE

    Travis joined Insight in 2019 as an EVP on the Insight Onsite team. Travis partners with portfolio company CEOs and their leadership teams to build scalable and effective go-to-market strategies. Leveraging his more than 20 years of experience in sales, inside sales, and sales operations, Travis consults with portfolio companies to address…