Quarter four will be here before you know it — and those three months of excitement lead right into the sales kickoff. If you want to make sure your SKO brings your sellers together and sends them into 2024 with clarity and purpose, now is the time to begin planning. 

Many organizations are still balancing the advantages of virtual and hybrid events with the community building that takes place when you bring your team together in one room. Whatever path makes the most sense for your organization, our guests today make it clear that the place to start is with a vision statement — and from there you can layer on the creative elements, education, content, speakers, and swag that make for a standout SKO. 

Sailpoint continuously goes above and beyond to deliver top-quality SKOs that fuel growth. So it was a genuine delight to bring in Barrett Sellers, VP of global revenue enablement, and Robin Barde, associate manager of global revenue enablement to discuss the practical and replicable approaches they take to designing a kick-ass SKO, which you can emulate as you launch your team into the new year. 

We discuss:

  • Why you need a vision deck, a whiteboard (or two), and a t-shirt cannon to fully visualize your SKO
  • How to navigate the unexpected challenges in the shift from virtual to in-person
  • The importance of fun, creative elements, and networking opportunities throughout your SKO to create a sense of community
  • Identifying the right speaker mix — from ensuring diversity to reinforcement and inspiration

Listen to “#88: A Practical Guide to Creating a Kick-Ass SKO” on Spreaker.


Fully visualizing your SKO with tools, tricks and a t-shirt cannon

Before you can build a truly impactful SKO, you have to start with a vision. While many build their vision with a top-down approach, Barrett suggests flipping that on its head.

“Our SKOs would never be successful without the team, because they get so engaged and excited. They help build the vision as well,” Barrett says. “We start by going up the ladder first, then pushing downstream.”

Barrett, Robin and their team begin by deciding the top three things they want to push across the entire SKO. These will be major takeaways the entire event can be built around. Most importantly, they work together across teams to decide which top points are most important for driving the team forward throughout the following year. 

“We define our vision for the year around three or four things we can drop down throughout the theme of any event we do. From there, we build a vision deck,” says Barrett.

The vision deck is vital for ensuring each event, activity or speaker at the SKO is in complete alignment with the main goals and ideas the team needs to embrace throughout the year. It’s a living document that can be revisited again and again throughout the event planning process. 

The art of drawing people in

Once you identify your central vision, you can shift your focus to building excitement and drawing in people. According to Robin, a T-shirt cannon never hurts. 

“Having fun with those moments in between the more serious or inspiring messaging, and giving the event some levity can really go a long way to make guests feel comfortable, welcome and valued,” Robin says.

Robin and her team make sure to set the stage with something unexpected — their tactics go beyond the traditional opening of the top speaker entering the room. Instead, Sailpoint shares something of a ‘commercial’ using creative video at the start of the event and again when returning from breaks. 

They also conclude the event with a creative element, gamify as much as possible and close out with awards and recognition.

Why a whiteboard belongs in every office for SKO planning

When it comes to planning out the specific events and agenda of an SKO the most important tools you can use are a whiteboard, a large room with plenty of space to pace, and collaboration. 

“We work best when we can collaborate well and brainstorm together,” Robin says. “A whiteboard is really helpful to visualize the whole event. Map out the different topics, your agenda, the days — last year we even mapped out the floorplans of the hotel.”

When working with a document or spreadsheet, you’re often limited by what you can see visually. By writing down the time, dates and locations of events, speakers and timeline, you can see how they will work together to drive your vision home across the team.

The team at Sailpoint used the whiteboard as their event planning source of truth. And while they found themselves redesigning, even wiping the board clean and starting over once or twice, the tool was crucial for providing a visual that allowed all team members to collaborate and brainstorm to design the best SKO possible. 

Following up with measurement

Building community and excitement are key for an impactful SKO. However, without measurement and feedback, there is no way to ensure the event is effective, and perhaps more importantly, can be iterated upon to truly drive home the vision.

By incorporating reinforcement throughout and following an event, you can ensure your team grasps the important concepts incorporated throughout the event. If any gaps are revealed, measurement also creates an opportunity to tailor follow-up training or meet-ups throughout the year for an SKO that will drive value in all four quarters.

Navigating unexpected challenges in the shift from virtual back to in-person

During the pandemic Sailpoint, like many organizations, had to shift their SKOs online. After completing two virtual SKOs, they shifted back to in-person — which proved more challenging than expected. 

Like many businesses—Challenger included—their leaders found that virtual training can actually be more effective. Taking tools and tricks learned from designing virtual training and translating them for use throughout in-person SKOs can be incredibly helpful for retention and engagement.

The shift back to in-person events elicited a mix of reactions from Sailpoint’s sellers. Many people enjoyed the virtual events because they could play, replay, pause and restart whenever they wanted. It was acceptable to get up, grab a coffee and let their dog out. In-person events are typically more rigid, and traditionally, include sessions as long as 8 hours. 

“That’s one thing we’ve taken from virtual,” Barrett says. “Eight-hour long sessions are no longer a thing for us. We try to do short, quick sessions unless they’re breakouts. We try to keep those about 30 minutes, because any longer and you lose attention.”

How to create a sense of community with creative elements, networking opportunities and injecting fun throughout your event

One of the largest benefits of shifting SKOs back to in-person is the added value of networking. In addition to focusing on the themes and vision for the SKO, leaning into the benefits of networking by incorporating brainstorming sessions, break-outs and specified time for connection build camaraderie and motivation for the year to come. 

Sailpoint also relies heavily on creativity when designing and executing SKOs. Gamification is a major way the team injects fun into the event.

Over their two previous virtual SKOs, Robin and Barrett’s teams leveraged apps, platforms and outside teams to gamify the events. When shifting back to in-person, they worked with outside agencies to retain the fun and creativity throughout their live event.

“It’s helpful to think outside the box and outside your team,” Robin says. “It’s about the experience for your audience. How can you make it the best event possible, while also keeping in mind that budget?”

What matters most when identifying the right speaker mix

When deciding on keynotes, speakers and activities it is essential to consider diversity. When sellers see themselves represented on stage, it can be incredibly empowering. Sellers need to see themselves throughout the event, whether through speakers, awards or leadership roles.

“We integrate stories and speakers from all over the world,” says Barrett. “We really try to pay attention to our global partners so they have an opportunity to be on stage and talk about how well we work together, how the relationship contributed to the win of a deal.” 

In addition to featuring stories and leaders from all over the world, Robin emphasizes the importance of featuring a diverse set of voices. 

“As far as representation we highlight our rockstar sellers, men and women,” she says. “We give our women leaders a platform to give a keynote or hold a session.”

By representing the diversity of your sales team throughout your SKO, you invite all attendees to recognize they are a critical part of the community and will play an instrumental role in achieving the overall vision for the year. Without diversity, you risk devaluing your overall message. 

Want to learn more about designing a kick-ass SKO? Listen to the full episode of Winning the Challenger Sale where Barrett and Robin reveal more about incorporating lessons learned from virtual events into live, injecting fun, community and creativity throughout, and ramping up diversity for ultimate motivation and representation.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

Andee Harris

Andee Harris is CEO of Challenger. Andee brings more than two decades of experience growing and scaling service and technology businesses. She has previously led multiple companies, both as CEO and Senior Vice President, through periods of rapid revenue growth, critical fundraising, and successful acquisition. These companies include Highground (acquired by Vista Equity Partners), TMBC (acquired by ADP), Syndio and Emerging Solutions (acquired by Emtec).