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The Playbook for a Successful Sales Kickoff

Posted in:  Company, Sales, Sales Enablement

Picture this: You plod into a conference center expecting endless slides and nap-worthy sessions. Instead, you’re met with Journey bumping through the speakers, a breakfast buffet, and colleagues who have either had unhealthy amounts of coffee, or who are genuinely pumped to be at your company’s yearly sales kickoff (SKO) — or both!

This was the scene at Highspot Momentum 2019 — our excuse to spend two days celebrating (and analyzing) our collective wins, learning from customers including Apptio, SAP Concur, and PitchBook, and getting energized about the year ahead. Our goal was straight-forward: create an SKO experience this year that will still be the gold standard five years from now.

As one of the most important initiatives of the year, and a huge company investment, SKOs serve critical purposes:

  1. Educate: Provide an overview of sales strategies, product updates, and best practices — equipping reps with the knowledge they need to excel.
  2. Celebrate: Recap the year’s accomplishments, making sure teams feel recognized and appreciated for their hard work.
  3. Inspire: Light a fire and create momentum heading into the next year (get it?), with everyone feeling set up for success.

Modern companies know the modern buyer has changed. They also know that successful SKOs aren’t made in a dark room with detailed PowerPoint slides. Just as the rules of engagement have evolved, so have the rules of launching the year with a dynamic and memorable SKO. While no two SKOs are the same, there are core plays that you can run to ensure your kickoff lays the foundation for a legendary year.

Sell Your Sales Kickoff Early and Often

Unless you’re hosting a dreamy destination gathering or having [insert your favorite artist here] headline, SKOs typically aren’t must-see events to get hyped about. Too often dismissed as “back to school” for reps, SKOs need proper promotion to build team excitement. Modern sales enablement teams understand that while they have deep insight into SKO value, they still need to spark reps’ interest. You must energize the sales organization with frequent, compelling information that convinces them that your SKO will be the single best thing since sliced bread. There are a few ways you can go about this:

  • Choose a theme: The most memorable events are often united by a central idea. Keep your SKO focused and entertaining with an overarching theme that unites all content. Doing so provides fun opportunities to enhance presentations, competitions, swag and more — giving your SKO the best chance of going down in company history.
  • Look to leadership: If your SKO involves multiple departments, connect with those department heads. The people leading each segment of your audience are the same ones who need to be shouting from the mountain tops that the SKO will be an incredible experience.
  • Start the party early: SKOs are a heavy investment and deserve more than 15 minutes of fame. Give your audience early visual cues, from branded content and swag to a promotional video. Where do reps typically work in their day to day? Promote there.

sko best practices

Keep the Energy High

SKOs are generally a time for “out with the old and in with the new” when it comes to process changes, updated messaging for the GTM teams, or new tool rollouts. But the real goal of SKOs is to energize, inspire, and focus your sales team. It’s expensive to take everyone out of the field for a few days, so you need to ensure the entire team benefits from the experience. Rebuilding buzz is a difficult task when your teams are dozing off from minutiae and praying that they’re not called on to answer questions. So how do you keep the soul train going?

  • Mix and match: It makes sense to pair process with process and workshop with workshop, but repetitive sessions will lull people into slumber. Instead, sprinkle less energetic sessions among the rest. One of the biggest energizers at Highspot Momentum was a Family Feud-style competition where reps battled head-to-head to answer product- and competitor-related quiz questions.
  • Pump it up: A well-curated playlist is a simple, yet powerful way to keep the energy going between sessions. If you do it right, you might even inspire a few singalongs. Here’s an example of what we put together.
  • Spotlight value: Consistently highlight the impact for the individual — the most critical takeaway for your audience. Each session must check the “what’s in it for me” box.

highspot sko

Celebrate Wins and Winners — And Create More While You’re At It

A common piece of feedback from our 2019 SKO was, “Let’s turn our wins into something everyone can take back and use.” You’re likely already celebrating your big wins and top performers from the previous year, but what does that mean to the rest of the team? Celebration for the sake of celebration has minimal value. Instead, turn victories into tangible success patterns everyone can use. What lessons do a major deal or a top rep’s success teach the team? Give your audience new knowledge and secret weapons to close more deals with these tactics:

  • Interview your top performers: They’re winning for a reason, but why? Sit down with your star performers before SKO and dig into their approach. What was the biggest improvement they made this year? How would they package that knowledge and give it to the rest of the team? At the event, translate these learnings into actionable insights for reps.
  • Straight from the horse’s mouth: Include your customers! Sales reps are used to hearing win stories only through their teammates or a win alert email. The customer’s perspective is invaluable, but it rarely makes it back to the rest of the team. Invite customers to speak at your kickoff, and don’t be afraid to ask them direct questions that reveal meaningful insights. We were honored to have SAP Concur, Apptio, and PitchBook join us this year, which offered unique face time for our reps as well as a forum for questions. On top of that, it was a whole lot of fun to have the people we care about and prioritize every day at our event! As a post-event follow-up item, the sales enablement team distributed an action-oriented summary of the sessions.

highspot sko customers

Different Intentions, Different Rooms, Different People

Imagine this — you’re rolling out a new tool, but “rolling out the tool” is not the intent. The intent is to get your reps excited about the new tool and the positive impact it’s going to have on their day-to-day. To ignite excitement, you need the right medium, the right person, and the right setting. For example, one of our technology customers produced two professional hype videos about Highspot’s capabilities that they played at their company SKO. These videos served to introduce Highspot to the team, highlight its powerful capabilities, and encourage usage in an engaging format that resonated with the audience and mapped to the intent. The end result? An extremely high adoption rate.

When you’re planning sessions, keep these pointers in mind to ensure your intent lands the desired outcome:

  • Which setting will support your intent? You may or may not be at the size where you need to book multiple rooms, but know this — different rooms serve different purposes. What does this mean? Think about it. What are you trying to accomplish with each session? Are you trying to light a fire to the point where everyone is — seriously, play this one out in your head — chanting your company name and hoisting chairs above their heads? Or are you leaning on your audience to help drive the session and you need something a little more intimate? The point is that most people feel more comfortable speaking up in a room of 10 than a room of 200.
  • Which presenter is going to fulfill that intent? This needs to be unique to every session. If your CEO is mild-mannered, they may not be the best person to ignite the aforementioned chair hoisting session. Likewise, consider having reps lead sessions!

highspot momentum photobooth

At the end of the day, the best measure of SKO success is not the number of naps avoided, nor the gallons of coffee drained — it’s the morale of your people when they walk out the door. At Highspot, our people are our primary success factor and the number-one reason why we love coming to work every day. Highspot Momentum was designed to ensure that everyone returned to their daily work inspired, confident, closer with their teammates, more informed, and eager to seize the opportunity in the year ahead. Time will tell if we hit the mark, but we’re already seeing tangible results in the first few weeks post-SKO.

Done well, your SKO will fuel the momentum of your company in the year ahead, and take you to places above and beyond.

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