10 Tips for Executing a Successful Virtual Sales Kickoff (SKO) – Sales Enablement Diaries

This guest post is written by Celine Grey, who leads Global Sales Enablement at Peakon, a Workday company.

Wondering how to run your virtual sales kickoff? 

It’s likely that your most recent SKOs look much different than the SKOs of prior years. As with most aspects of remote work, taking what was historically a face-to-face event and repurposing it for a fully virtual environment can feel like quite the challenge. 

Luckily, we just wrapped up Peakon’s virtual sales kickoff and are walking away with a myriad of learnings. Despite all of the ways that our virtual SKO looked different from our typical in-person gathering, we discovered many perks to hosting a 100% online SKO.

To help you plan your next virtual sales kickoff, I’m sharing 10 tips to help you prepare, think outside the box, and use your SKO as a launching-off point for ongoing learning:

1. 1. Restructure using half days
   2. Identify a common theme
   3. Help speakers prepare
   4. Bring in external guests
   5. Consider your audience
   6. Mix up session formats
   7. Over-communicate before, during, and after the event
   8. Make sessions fun and interactive
   9. Capture and repurpose SKO content
   10. Gather (and implement) feedback

Prepare with intention

A hallmark event for any sales org, sales kickoffs offer an important opportunity to gather your entire go-to-market team to outline goals, expectations, new product information, and recommended sales strategies to drive your organization’s success. With the right forethought, you can ensure that your virtual sales kickoff will be an enjoyable, memorable, and enlightening experience.

Tip #1: Restructure using half days

In a virtual environment, you have the freedom to think beyond the confines that an in-person SKO involving travel and lodging might entail. Consider spreading the event over multiple days. We decided to spread our SKO over several half days—which worked in our favor for several reasons. Go-to-market teams were still able to accomplish work each day; as a result, they came to each of the half-day sessions attentive and engaged, not worrying about a growing back-log of work. The half-day structure also helped us to avoid potential Zoom fatigue amongst attendees. 

Tip #2: Identify a common theme

Identify a universal theme that encompases all of your high level objectives for the SKO. Tying a theme to your event emphasizes the key takeaways your teams should focus on. It also generates excitement and motivational energy at the event. A memorable theme offers a cohesive message to refer back to throughout the year to remind your teams of the goals and topics covered during your SKO. 

Tip #3: Help speakers prepare

Collaborate closely with your speakers throughout the planning process—even before they start building out their presentations. You’ll want to ensure that their message will resonate with the audience and relate back to the key objectives of the SKO. Flushing out topics with presenters ahead of time will allow you to identify common threads among speakers and structure the order of presentations accordingly. 

Tip #4: Bring in external guests

As you recruit team members to lead SKO sessions, also consider bringing in external guest speakers. With hosting outside speakers as simple as sharing a Zoom link, consider bringing in customers, industry leaders, or motivational speakers to provide fresh perspectives throughout your SKO. 

Pro Tip: Consider scheduling prep time or an SKO rehearsal with all internal and external speakers to practice presentations before the actual event. Utilize this time to iron out any technical issues or questions.

Tip #5: Consider your audience

For many organizations, the SKO audience extends beyond the sales org to include the entire go-to-market team (marketing, customer success, etc.). With so many diverse perspectives, you’ll want to plan main event sessions that are relevant to the entire audience. Save niche, laser-focused topics for smaller group sessions that are clearly segmented by role and responsibilities. Building out each session with the audience in mind will not only increase engagement, but help with contextualizing information for session attendees.  

Think outside the box

Although moving SKOs from an in-person gathering to a virtual event may feel like a daunting task, resist the urge to simply copy an agenda that worked for your in person SKO and bring it to your online program. Instead, reimagine your SKO format and consider the opportunities and benefits of a virtual event. 

Here are some of the ways our team was able to replicate the collaboration and excitement of an in-person SKO for our virtual attendees.

Tip #6: Mix up session formats

By blending together a variety of formats to deliver content, you can drive engagement and create memorable moments. For more formal sessions, a blend of presentations, fireside chats, and panel discussions are ideal for delivering key information. With less structured topics, or sessions that will require attendees to brainstorm and share ideas, try interactive group workshops, roundtable discussions, and games to drive audience participation. 

Pro Tip: Regardless of the format or topic, invite your audience to utilize one of the best benefits of a virtual SKO—the chat feature! You’ll likely see a correlation between a lively chat box and audience engagement. Plus, you can use the chat feature to track audience questions, allowing you to address more comments than you would be able to during an in-person session.

Tip #7: Over-communicate before, during, and after the event

Over-communication is crucial to team success in a virtual environment, and SKO is no exception. We utilized the following communication methods to supplement face-to-face communication:

1. 1. • Know-before-you-go calls: Before each half day of the SKO, we scheduled 10 minute calls to rally our team, lay out logistics, set expectations, and built momentum for the day ahead. These calls ensured everyone had the information they needed to head into the event—plus our check-ins generated excitement for the sessions ahead. 
      • SKO Slack channel: We developed a SKO Slack channel as a way to communicate bits of information throughout the week of SKO. We used the channel to release information about our speakers, share collateral and instructions related to each session, and track any questions or comments from our audience.
      • Publish session recordings: After each session, we quickly edited and published the session recording in our WorkRamp resource library. This allowed attendees to review any sessions they missed or wanted to revisit while the information was still top-of-mind.
      • Schedule follow-up sessions: During SKO events, GTM teams are bombarded with new information. We scheduled several deep-dive follow-up sessions after the conclusion of our SKO to ensure we could answer questions from our teams and build upon the knowledge shared in each session while it was still fresh in everyone’s mind.

Tip #8: Make sessions fun and interactive

Whether your SKO is one day-long event or several half-day commitments, attendees are subject to a lot of new information. To combat cognitive overload, schedule mini social breakout sessions and games throughout the event. Games like jeopardy, word bingo, and even virtual escape rooms and murder mysteries encourage team bonding and help create fun memories of SKO. 

Consider your SKO a launching-off point

A great SKO lives far beyond its dates on the calendar. Consider opportunities to transform SKO sessions into evergreen content to power learning experiences throughout the year. As you revisit the lessons of your SKO, work with your team to understand which sessions were the most impactful—and which sessions should be improved for your next event.

Tip #9: Capture and repurpose SKO content

SKO events provide great insight into company strategy, as well as short and long-term goals. Therefore, they offer great foundational learning for new hires joining your organization. If timing allows, consider inviting new team members to your SKO during their onboarding process. Better yet, include recordings of your SKO sessions in your LMS onboarding guide for new hires. 

Pro Tip: Beyond using SKO session recordings for learning guide content, you can also use information from sessions to build sales collateral and one-pagers to help your reps throughout the year.

Tip #10: Gather (and implement) feedback

Perhaps more so than with an in-person SKO, you can truly measure engagement and quickly gather feedback with a virtual SKO. Pay attention to how engaged team members seem during interactive breakout sessions and monitor chat activity throughout each session. You should also consider formally soliciting feedback throughout the event and at the conclusion of the SKO. 

If you are structuring your SKO as a multiple-day process, you utilize team members’ feedback to improve the following day’s event—otherwise you can take feedback into your planning for your next SKO. The information you gather from your teams will help you plan follow-up activities and build better kickoff and team events in the future.

Design a plan as unique as your team 

While SKOs will inevitably look different in the era of remote work, they represent an opportunity to get creative, unite teams, and motivate better GTM practices. These ten steps helped our team at Peakon execute an engaging and memorable SKO, but each organization is unique. Use these steps as a foundation to build an SKO plan that will set your teams up for ongoing success.

Feel free to contact me directly if you would like to learn more about Peakon’s approach to virtual SKOs or connect with some of the partners who helped us with our event. 

Learn how Peakon, a Workday company, built and deployed its global sales enablement program in just 8 short weeks – leading to increased revenue growth and rep satisfaction.

Special thanks to Celine Grey, for authoring this guest post.