How to throw a successful (virtual) sales kickoff

Posted January 11, 2021

By Cari Murray

Senior Editor at Outreach

With limitations on travel and events, sales kickoffs (SKOs) are going virtual this year. That’s tough at a time when a morale boost is greatly needed. Especially when sales teams used to rely on the energy and celebration from in-person SKOs to build momentum for the year ahead.

While we could let that get us down, we'd rather reimagine the sales kickoff — one that all salespeople enjoy attending, even if it’s from behind a monitor. It’s important to get it right not only to motivate your sales team about going to market right now, but also simply for mental health.

So, how do you keep your SKO exciting, energizing, and inspirational all while delivering important sales and product education?

Here’s the Outreach playbook on what to consider before, during, and after your virtual sales kickoff…

Pre-Event: Account for the Differences

First things first, throw out any language like, “we’ve always done it this way.” You simply can’t execute a SKO the same way you did before.

In-person SKOs were hours of content per day where salespeople were expected to sit and consume. Let’s face it, by the end of the day it’s hard to be engaged or retain any new information. Now, we have the exciting opportunity to take a step back, consider the outcomes we want to see, and think about even better ways to drive those outcomes.

Ask yourself and your sales team, why are we doing this? What do you want to see? We did this when we took Unleash from an in-person event to virtual in eight weeks. We used that information as our guiding principles for building the strategic plan, creating our content, and implementing the technology needed for virtual engagement.

At the same time, people have a lot of distractions in the virtual environment. So, consider a shorter event over two to three days versus an entire week. Make the content quick and easy to consume while potentially mixing live and on-demand sessions. There is certainly value in experiencing it together, but for some topics it may not be required.

Another consideration should be around building community and engagement before the event begins. An example of this was when we threw a virtual 90s dance party over LinkedIn a few days before the Unleash Virtual Summit to get people excited. I’m not saying you have to throw on Whitney Houston (although it certainly helps!), but consider sharing a video or two to hype the event.

The bottom line is that your virtual SKO doesn’t have to be one size fits all — and it doesn’t have to be boring.

During the Event: Take a Creative Approach to Building Camaraderie

Salespeople want to learn from peers and experts, hear what’s successful, and connect with each other. Make sure that’s not missing from your virtual event.

What’s great about the virtual environment is you can be even more intentional about grouping people together for networking or breakout sessions. Whether you want to connect salespeople at different career levels or in varying roles, you can segment them in ways that build important internal relationships for years to come.

Throw in some fun. While we can’t be together physically, we can still create an active virtual environment. Incorporate live polls to boost engagement and help set a "choose-your-own-adventure" agenda throughout the day. If energy levels seem to drop, be open to switching topics based on in-the-moment feedback you receive.

Virtual sales kickoffs have a surprising and wonderful benefit. Before it would have been too costly to invite everyone's partner or family members to a SKO. Now, they can get involved, too! Whether it’s sending a mixology kit to their homes or organizing a morning yoga session, you can help them bring home and work together.

Sales teams thrive on competition. And competition can encourage engagement. In the virtual world, it’s called gamification. So, why not gamify your SKO? That could look like taking a short quiz at the end of a session and receiving points for how well they did. It could also be rewarding salespeople for participation. Then, build a leaderboard that the entire company can see in real time.

Awards are typically a big part of SKOs, but a virtual event doesn’t mean they have to be less important. Think about what will resonate most with your team. Maybe it’s pre-recorded kudos videos from their manager. Or 30-second winners' speeches where they share what made them successful. Or custom graphics and photo montages that you share on the screen while giving out the awards.

The important point here is that you don’t want your people to feel like bystanders. You want them to be part of the experience, strengthening relationships and building momentum despite the distance.

Post-Event: Ensure Your Team Executes on Strategy

At the end of an SKO, sales teams are typically riding high with energy and momentum. It’s crucial to keep that momentum going, especially in today’s remote sales world.

The great news about a virtual event is you can continue to use all that content. What used to be a one-time kickoff can now become bite-sized SKO-type events for the entire year. For a session that really hit home, consider holding an encore session a few months later. Invite the presenter back for a live Q&A. This reinforces the message and gives reps another chance to engage an expert.

Momentum also comes from the energy created when people learn from each other and build relationships. Look for ways to keep that positive momentum and celebration throughout the year, connecting reps who can learn from each other.

Making sure that your salespeople are in a position to win is critical. One way to do that is to let your people focus on what matters, removing the manual work with sales engagement tools. This gives your teams back precious time to engage with their clients, enhance their social selling skills, or to restore and replenish themselves.

Speaking of digital tools, salespeople must lean into and adopt the technology they have at hand. In an increasingly digital world, modern technology helps sales organizations reach customers in new ways, glean critical insights, and deliver targeted, high-quality content at scale. Our customers will tell you that investment pays off:

“One of the first things we did, actually, was invest in a sales acceleration and enablement tool,” shared Britney Bartlett, senior director of Global Virtual Sales Specialists at Cisco. “Outreach was one of the first things that we looked at. We have seen dramatic results. It genuinely has increased productivity in terms of number of touches per rep by over 40 percent.”


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