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How to Land a Successful Virtual Sales Kickoff in 2021

Posted in:  Sales, Sales Training
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Sales kickoffs — or SKOs — are essential for every sales organization’s success.

Not only are they key to landing your go-to-market strategy for the upcoming year, but they are also one of the few times your entire sales team will be together, making them valuable opportunities for camaraderie and connection.

Though in-person SKOs may no longer be possible, that doesn’t mean you can’t deliver a show-stopping virtual event. The key is to focus on educating and inspiring your team at three critical points — pre-, during-, and post-SKO — so they have the training and motivation they need to succeed in the new year. In this guide, we’ll break down exactly how to do that virtually by answering questions like:

What Makes Sales Kickoff Training Effective?

Companies invest in annual sales kickoffs for three reasons: to inspire, motivate, and educate their sales teams. These annual meetings are a time to land your strategy for the upcoming year, including tool or organizational changes, or new initiatives.

That’s a lot of ground to cover in just a few days, which means every minute of your sales kickoff must be carefully planned to maximize the impact of your investment. To ensure you efforts are landing effectively — and that your team is getting the training they need — in a virtual SKO setting, ask yourself these questions.

  • What do you want to accomplish with your SKO?
    • Think about: strategy, tools, key initiatives, organization/incentive structures
  • How are you measuring the success of your SKO?
    • Think about: training content engagement, rep feedback, revenue impact
  • Which tools will help you achieve these goals?
    • Think about: virtual event platforms, sales enablement platforms, social/communication platforms 

Your answers to these questions will lay out the “what, why, and how” of your virtual SKO. Together, they will create a framework for how you approach your SKO training to ensure you land it effectively.

Once you have your basic plan outlined, the next three sections will give you tactical tips to put it into action.

How to Prepare for a Virtual SKO

The weeks leading up to SKO are an essential time to get your sales team excited and prepped for SKO. Two to three weeks before the big event, here’s what to focus on.


The last thing you want to do is virtually lecture SKO attendees over Zoom. Instead, plan to have the majority of your educational materials available and assigned a few weeks ahead of your event date. Use your sales enablement platform to deliver bite-sized lessons, personalizing content for sales team segments as necessary.

Says Kendall Michaud, Revenue Enablement Manager at Highspot, “Pre-work gives your salespeople ample time to get familiar with the materials, complete all necessary certifications, and prepare questions for a live discussion.”


Pre-SKO, it’s also important to make the value of the event clear to attendees. This ensures that attendees take the aforementioned pre-work seriously and that they show up ready to participate on the day of.

Focus on “selling” your sales team on SKO — just as you would with buyers, clarify the value they will receive by attending, and set expectations appropriately. For instance, Kendall recommends “releasing the agenda in advance of the event” so attendees know what’s in store. “Oftentimes, salespeople assume they’re just going to get lectured — but if they can see all the fun events planned, it changes their expectations.”

How to Engage Salespeople During a Virtual SKO

The big day has finally arrived — which means it’s time to shift your attention to keeping the momentum you worked so hard to build going. Start with these tips.


Here, your focus should be on leading dynamic live engagements that maximize the impact of your time together. Think about how you can make the sessions as interactive and relevant as possible for each attendee; for instance, you could create custom tracks for each sales persona. Additionally, think about how to bring salespeople into the conversation, whether that’s by actively calling on attendees or by hosting sessions in a Socratic seminar format.

Finally, “no session should be longer than twenty minutes,” Kendall said. “Past that point, you’ll start to lose people’s focus.”


SKOs don’t have to be all work and no play. In fact, a little fun during the virtual event is often a welcome break from business-oriented conversations. Look for ways to inspire your sales team through guest speakers, motivational keynotes from public figures, or even bonding activities such as virtual cooking lessons from a local restaurant.

Said Kendall, “Creativity is key to landing an inspirational SKO. Put yourself in the mind of the seller — what would make you pumped to go back to work and sell the next day?”

How to Continue Training Post SKO

The impact of your SKO doesn’t end once the event is over. Reinforcement of key learnings will ensure your strategy is put into action once reps return to the field. 


That means you must continue to educate your sales team long after SKO has come and gone. First, upload recordings of SKO sessions to your sales enablement platform so salespeople can reference them on an as-needed basis. “Since some recordings will be up to twenty minutes long, consider chopping up learnings into even smaller sessions that reps can easily consume during their workday,” suggested Kendall. 

Additionally, use analytics to continually evolve your ongoing training materials. In the weeks after SKO, check to see which content reps have returned to and map their behavior against their performance. Explained Kendall, “This will reveal which materials are actually having an impact on revenue so you can do more of what works and less of what doesn’t.”


To keep momentum strong after SKO, it’s important to celebrate wins. Look for ways in which salespeople are successfully applying the lessons learned during the event and then share those achievements with your team. Said Kendall, “Remote work means we can’t celebrate victories the same way, so little call-outs can make a big difference in motivation.”

Borrow a method Kendall uses and set up a best-practices Slack channel where coworkers can cheer each other on and share wins with their team.

What Are the Best 2021 Sales Kickoff Themes?

Now that you have your sales kickoff plan fully built, it’s time to put the finishing touches on your approach — namely, thinking about your theme.

Theming your SKO rallies your sales team around something inspiration and contributes greatly to the energy at the event. Here are some ideas to consider:

  • A Whole New World
  • Accelerate
  • Achieve
  • Amp Up
  • Believe
  • Beyond
  • Breakthrough
  • Carpe Diem
  • Connect
  • Elevate
  • Great Expectations
  • Homecoming
  • Ignite
  • In It to Win It
  • Infinity and Beyond
  • Leading the Pack
  • Liftoff
  • Mission: (Your 2021 Strategy)
  • Momentum
  • Moonshot
  • New Frontiers
  • Onwards and Upwards
  • Power On
  • Ready, Set, Sell
  • Rise
  • Showtime
  • Summit
  • Synergize
  • The (Your Company) Experience
  • The Future Is Now
  • Unleash
  • Uplift

A Successful SKO, No Matter Where You Work

With the right approach — and strategic use of your enablement platform — you can deliver a SKO that leaves your team feeling educated, inspired, and ready to conquer the new year.

Ready to start planning? Download our virtual SKO kit for the best practices, customer tips, and more.

how to land a successful virtual sales kickoff in 2021

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