How to Plan Truly Incredible Virtual Sales Kickoffs (2023 Edition)

How to Plan Truly Incredible Virtual Sales Kickoffs (2023 Edition)

It’s probably been a while, but was the last in-person sales summit you attended a once-in-a-lifetime, career-defining experience? Probably not.

Sales kickoff (SKO) events are often long, expensive get-togethers that leave attendees looking forward to the flight home. They might be flashy, but they lack engagement opportunities that would make them truly useful and memorable experiences.

Virtual events have the potential to change the game

COVID-19 seems to have changed the business world for good, so much so that almost all annual sales summits are slated to be virtual-only events. And although the knee-jerk reaction is to assume that’s a bad thing, the reality is that a digital SKO could actually be an improvement.

Here’s why. Most SKO planning takes place at the beginning of the fiscal year. During this time, executives and sellers are closing out the prior year, and they don’t have the bandwidth to do content reviews or provide input that would make the experience more relevant. As a result, planning is usually left to an events team that simply tries to replicate the prior year’s event, perhaps with some incremental improvements thrown into the mix.

Maybe we should book a popular motivational speaker.

What about a better band?

Should we do the networking casino night again?

Traditional events are too long and too expensive

Most clients have a standardized way of doing these events. Speakers get their 90-minute time slots; that’s the way it’s always been, but this format doesn’t maximize value for speakers or attendees. In an age where attention spans are about as long as the title slide of a PowerPoint presentation, wouldn’t it be better to deliver more impactful information in the shortest amount of time possible?

The standard experience itself is simply too long and too expensive. We’re all familiar with the typical SKO setup — a three-day event in a massive rented-out ballroom in Las Vegas. Case in point: a client that spent $70 million on its last SKO after accounting for flights, hotels, food, and everything else in the budget.

That’s too much money for an experience that doesn’t place enough focus on attendees’ emotional and mental presence (engagement), peer-to-peer sharing, presenting practical wisdom, or applying SKO insights back in the field. In fact, around three-quarters of organizations lack follow-up training after their annual SKO events.

No matter how creative, fun, and potentially relevant the event’s content is, no one in the audience is paying attention by the third day. The opportunities to network and socialize are nice, but they don’t justify the enormous price tag — especially for sellers who might be leaving the office when customers need them most.

Actually, if you’re a seller, SKOs can become three-day anxiety attacks. Salespeople spend just 28% of their time actually selling. That means in-person events leave even less time for them to do the most important parts of their jobs. And if sellers have to leave halfway through a session to take care of a customer call, the company that paid for them to be there might as well be burning dollar bills.

What makes virtual SKOs so much better?

Virtual SKOs have five major advantages over in-person events.

1. They’re more relevant. Rather than staging one massive SKO event each year, virtual summits can be delivered on-demand and as needed to match the rhythm of the business cycle. They can center on the most timely, relevant information that’s needed in the field now (rather than six months from now).

2. They’re shorter. Virtual summits are generally shorter, and they place a priority on meaningful engagement over suitable entertainment. Shorter time blocks mean presenters have to be more thoughtful and disciplined in their delivery. They have to quickly hone in on the most important information they want to relay.

3. They can be much more personalized. A virtual format allows for a tremendous amount of data collection. This data collection lets the host speak directly to attendees, track engagement, and conduct more targeted analyses of regional and role differences.

Modern marketing has conditioned us to prefer personalized content. Just look at Instagram, Facebook, or any other social platform that delivers content based on the swaths of data social media companies have collected from users. And yet, when you attend the typical large, in-person SKO event, you get information that’s maybe relevant to you… but not really.

4. They offer more flexibility. This format allows for the customization of on-the-fly modules and real-time adjustments that are engaging, drive retention and application, and curate input and ownership from the field. Certain modules can even be scaled beyond a one-time event to provide ongoing value as a teaching or onboarding tool.

Flexibility transfers as ease of access for attendees. In a recent survey of people attending virtual events, 77% of people said they preferred virtual versions because they were simply easier than going in person.

5. They’re far cheaper. Most importantly, a virtual format lowers event costs significantly for the host and the attendees. This allows for a wider audience, more individualized learning, and post-summit reinforcement with user-driven adaptive learning practices.

How to craft the perfect virtual sales kickoff

Of course, these advantages are largely hypothetical right now. We haven’t seen the long-term potential of virtual summits just yet. But in an attempt to help bring that potential to life, here are a few tips for anyone planning a virtual SKO.

Create a purpose-built experience for a virtual audience: Virtual SKOs are never going to be the same as an in-person event. And that’s OK. Don’t try to replicate previous in-person experiences. Take the opportunity to make something that stands out.

Instead of designing a one-size-fits-all experience intended for many sellers, create multitrack topics. Break up the audience to make sure your content is relevant for each of the various selling teams’ roles.

Rather than relying on one-way presentations that don’t ask for input or engagement, support interaction by including time for reflective questioning and crowdsource input from the audience during plenary sessions. Keep the format flexible and shift quickly from one activity to another to maintain engagement.

It’s sales, so incorporate competition — and keep things fun: People will miss the camaraderie they’ve come to expect from their annual events. Be sure to plan out non-learning activities — think networking, peer sharing, icebreakers, and so on — to help attendees relax and make a connection.

Gamification is a great way to reinforce learning. Create competition with small-group breakout exercises and self-paced challenges so that attendees can practice applying information learned in the plenary session (competition can start with pre-work as well). To make this approach effective, planners must be intentional about assigning attendees to breakout groups. Learn about your participants, segment them by role and experience level, and provide them with a truly tailored experience.

Make virtual participation as easy and seamless as possible: Regardless of what technology you use, it must come with a low barrier to entry. Don’t force attendees to download additional plug-ins or software, and make sure that bandwidth requirements are kept low so anyone can join from anywhere.

Once participants have registered, a simple calendar invite is the only thing they should need to attend. If there are additional instructions, dial-in numbers, or passwords, include them in the invite. Similarly, make sure your speakers can present in an audience’s ideal time zone and language whenever possible. This could mean creating groups of participants based on geographical regions. In short, don’t make your West Coast sellers wake up two hours earlier to show up for a session at 9 a.m. CST.

Dos and Don’ts

To summarize, let’s run through all of the best practices to implement during your own virtual event (as well as some to avoid):

Best practices

  • Create a designed experience that’s built purposely for a diverse virtual audience.
  • Design multitrack topics and break up your audience to ensure relevancy within different selling roles.
  • Support the processing and internalization of information by pausing to pose reflective questions. Likewise, crowdsource input from audiences during plenary sessions.
  • Create competition using small group breakout exercises and self-paced challenges to practice applying information learned in the plenary sessions.
  • Shift the format and nature of the session as well as types of activities to maintain engagement.
  • Ensure virtual technology is seamless with low barriers to entry.
  • Include non-learning activities to help attendees relax and make a connection (such as icebreakers or networking).

What to Avoid

  • Focus on replicating previous experiences by trying to virtualize every in-person aspect.
  • Design one experience and cover skill topics that all sellers will go through together (regardless of their interest areas and roles).
  • Deliver a one-way presentation that fails to solicit input or engagement from the virtual audience.

Upcoming virtual conferences will provide an interesting testing ground for this new SKO format. Not all of them will go off without a hitch, but if you’re planning a virtual SKO for the first time, don’t aim for perfection. Just try to take advantage of the growth potential this new format has to offer.

Pay attention to what works and what doesn’t, and make sure each attendee takes away something useful from the experience. If you can do that, chances are people will return for the next one. (In fact, they might even prefer your new format).


Updated by Kendra Fortmeyer @ Sales Hacker 2023

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