21 Tips To Plan Your Virtual 2021 Sales Kickoff Meeting

The sales kickoff meeting is a fixture of many companies’ sales calendars. Typically occurring at the turn of a new year, it’s when the organization comes together to motivate the sales team to win and win big! However, 2021 is like no other year. Most companies will forgo an in-person sales meeting and many of you will be transitioning your events to a virtual meeting. This transition, if not done well, creates a de-motivating situation and can adversely affect 2021 sales.

If you’ve been doing great in-person sales kickoffs in years past, congratulations! Now that you have to do it virtually, you need to still have a motivational, energizing event. The key is to reimagine what’s possible in a virtual sales kickoff meeting rather than just stuffing what you already know about in-person sales kickoff meetings into the same old boring Zoom room you see your team in everyday. 

I’ve participated in many in-person sales kickoff meetings over the decades. I’ve hosted them when I was a vice president of marketing of several companies and more recently have been a hired outside speaker at many sales kickoffs.

There's a tried-and-true formula for an in-person sales kickoff that you probably use. There are usually informational sessions including product announcements and discussions of the compensation plan. There’s loud music and hype. Frequently your team gets excited as outside speakers including professional athletes and experts in sales strategies and techniques take the stage.  

Taking that typical playbook for an in-person sales kickoff and making it virtual with the same elements delivered in the same way but in front of a camera is a recipe for disaster! 

In this article, based on the ideas in my various books are some ways to help you plan a great virtual sales kickoff. Those books include Standout Virtual Events: How to create an experience that your audience will love and The New Rules of Sales and Service: How to use agile selling, real-time customer engagement, big data, content, and storytelling to grow your business and my Wall Street Journal bestseller Fanocracy: Turning Fans into Customers and Customers into Fans.

But first, before I dig into the 21 tips, let’s talk about the most important lesson to offer your salespeople at your 2021 virtual sales kickoff. They will need to hone their skills for how to sell in the pandemic. Elements of this that I teach sales teams include how to sell effectively on LinkedIn, understanding the neuroscience of fandom that explains why video is a way to sell when you cannot meet in person, and how to engage with potential customers via social media.

21 tips to create a great virtual sales kickoff

1. Do not simply try to recreate the in-person sales kickoff you are familiar with digitally. Unfortunately, those organizations that just film what they are used to doing fail to find the right medium and methodology for virtual success.  

2. A virtual sales kickoff is neither a digital replica of an in-person sales kickoff, nor is it network news or a daytime talk show. Elements of each will impact the design of an ideal sales kickoff. But to build your best virtual sales kickoff, you need to rethink what is possible. It is human nature for us to take what we already know from an offline world and apply it online. Advertising agencies missed the web marketing revolution by focusing on annoying and interruptive ads. However, smart advertisers recognized that digital affords them unprecedented consumer understanding and the ability to deliver desirable information at the right time, in the right context. Don’t just produce what you know and put it online.

3. Virtual sales kickoffs are more like television than theater.  In a theatrical performance, the audience is present. Their feedback is immediate and palpable. Lighting, sound and production value all come into play and they can enhance or detract from a presentation. Stage performers sometimes struggle to transition to the screen because of the proximity to the camera and the lack of an in-person audience. Production values matter, but they are far from the same as those in a theater. Playing to a camera is very different from reacting to — and interacting with — a physical crowd. Yet without a doubt, connections can be made, and audiences can be informed and entertained. It is, however, a question of mastering a new medium.

4. For a virtual sales kickoff, realize that people’s attention spans are much shorter than if they were in a convention center or hotel ballroom. This means we need to maintain interest by mixing things up, adding elements of surprise, and including the audience as much as possible.

5. Speakers making the transition to speaking at virtual sales kickoffs will need to re-work their entire talk. The first step is to break the existing talk into chunks of about five to seven minutes. In this way, a 45-minute in-person keynote will become a virtual talk of six or eight sections. To mix up the format of the sections, speakers can use the breakout room feature if the platform has one, conduct a poll and analyze the results, show a short video and describe learnings from it, and conduct a short live interview, all in one talk. If a speaker can do all of those things in 45 minutes, the talk will be quite different from an in in-person talk, but it is dynamic and engaging in a way that is ideal for a screen.

6. If a speaker (your vice president of sales perhaps) isn’t comfortable delivering a virtual talk, an interview with a skilled moderator who can guide the conversation can be a terrific solution. Journalists make terrific interviewers, and many have experience in front of a camera. It will be critical to ensure that a panel moderator or interviewer for a fireside chat is highly comfortable with the subject matter, the medium, and confident enough to lead the discussion if it lulls or heads off track.

7. Virtual sales kickoffs should be shorter. Typical in-person sales kickoffs range in length from a full day to a week, with programming starting in the morning each day and frequently running through an after-party late into the night. Keynotes and panel discussions are usually an hour in length and “blocks” of programming time are usually 90 minutes to two or three hours, with networking and meal breaks in between. That model works when people are physically together in a convention center or hotel ballroom, but it is not ideal for virtual sales kickoffs. Shorter usually works better with virtual because people tend to multitask when participating in a virtual sales kickoff and many people are familiar with consuming short form content online, such as YouTube videos. I recommend that sessions be 15 - 30 minutes and no more than 3 hours of programming per day.

8. Ideally, virtual sales kickoff programming will include shorter 15 to 20-minute sessions. If you have longer keynotes, you can break them up into modules with the Q&A coming after a short break. Consider a typical network news program and how it is broken into segments with commercial breaks coming at regular intervals. While you do not need commercials in your virtual sales kickoff, you do need to break up content into shorter segments.

9. Great in-person sales kickoffs include ways for the audience to interact with one another. Networking is one of the main reasons people enjoy attending in-person sales kickoffs. Unfortunately, at your average webinar, there is not a lot of introducing yourselves to those seated nearby, or hallway serendipity. However, successful virtual sales kickoffs will leverage digital tools to enable networking, maybe even more effectively than in-person networking. Through different tools built into virtual event platforms attendees can chat with one another, live, as a speaker is presenting.

10. Presenters can use a breakout room feature as part of their talk, to put attendees into small groups of five or six people so they can interact for a few minutes about the subject being discussed. And after a talk, virtual meeting rooms can be set up where people who share common challenges and goals can collaborate based on the information they just learned. 

11. Virtual sales kickoffs should use chat tools that allow for attendees to interact with peers while presentations are going on. Attendees type into the chat feature of whichever events platform is being used. This gets the audience involved and turns a talk from passive to active.

12. If an event platform includes a polling feature, consider popping up a poll every 10-15 minutes or so. Polls can be particularly useful before a session goes to Q&A to get people buzzing about something thought provoking or controversial from a talk.

13. One aspect that is extremely limiting is when a virtual event platform is hardcoded so that presenters’ slides are way bigger than the video stream of the presenter. You want to be sure that the virtual sales kickoff audience can see the speakers, particularly in the case of marquee names, company executives, and featured keynotes. That may sound obvious, but many digital presentation platforms make the presentation slides big and the speaker tiny, with no options to modify the view. In this case, consider going with no slides or having the slides on a screen next to the speaker in a studio where you film the talk. 

14. Helping your presenters shine is an absolutely essential component of producing a successful virtual sales kickoff. Unfortunately, the vast majority of presenters at virtual sales kickoffs will simply set up their notebook computer (or worse, their smartphone) on a table and present. The lighting, sound, camera angle, etc. can, unfortunately, be of poor quality. 

15. Perform a technology check with speakers prior to the sales kickoff to make sure they are presenting well. Most in-person sales kickoffs provide speaker guidelines and prep calls. Your virtual sales kickoff should be held to at least the same standard. After all, making your speakers look good makes you look good too.

16. Most webinar and event platforms allow for either a live virtual presentation or the ability to play a pre-recorded presentation. There are pros and cons to each approach, so you will want to consider which one is best for your sales kickoff. Presenting live is great because a speaker can build in interactive elements into the talk. Using features built into the platforms such as chat, reactions, polling, and Q&A allow for the audience and the speaker to interact in real-time. Live content also creates incentive to be present during the actual sales kickoff in order to interact with fellow audience members and speakers and be “part of the conversation.” 

17. Traditional old-school webinars almost always have the ability for people to either participate live or watch the recording of the session at their convenience. While it is nice for people to be able to watch at a later date, the problem is that fewer people will participate live and the potential for interaction is reduced. I recommend that, whenever possible, you should go with a live presentation only and not offer a replay. There may be situations where this won’t work, such as part of the sales team being halfway around the world in the middle of their night. The ability to engage with the audience via chat, polling, and other interactive tools is very powerful so perhaps you do two sessions of a talk so everyone can participate live.

18. Surprisingly, a virtual sales kickoff where speakers talk directly to the camera in a warm and casual tone can feel more intimate than an in-person sales kickoff where the speaker is 30, 50, or even hundreds of feet away on a far-off stage. But it requires skill to look into that camera when every part of you wants to look at your slides, to peek at the attendee chat, or to check out at the video of participants.

19. Don’t overlook the technology required for the presenters. You may need to insist that speakers have, at a minimum, a good webcam, a good microphone, some lighting, and a way to raise the camera so it is at eye level (a stack of books work great for this).

• Background: A simple background without clutter is best. If the speaker lives in a small apartment that doesn’t have a suitable background, something like a Japanese shoji screen, or a white wall can be a good compromise. Tell them not to use a cheesy virtual background. This is even more true for larger virtual sales kickoffs. Image matters.  Besides the tacky nature of a virtual background, there’s also the problem with the “ghosting” effect that happens when a speaker moves. For a split second the virtual background disappears, and you can see the room behind.
• Camera placement: It is best when the camera is positioned at eye-level to the speaker, producing an image that to the audience looks about four feet away. Ideally, a good quality webcam should be used. 
• Lighting: Never position a speaker with windows or bright lights behind them. Their face should always be lit either by natural light or you can suggest that they purchase a small ring light.
• Microphone: Ideally, an external microphone like the Yeti model made by Blue Microphones should be used. Relying on the mic that is built into a computer can deliver poor quality sound, or worse, generate feedback. And speakers should be discouraged from using in-ear headphone/mic combinations, because of poor quality sound.
• Headphones: Any headphones will look less than ideal on camera. However, they do have a distinct benefit for speakers because they don’t cause feedback like using computer sound can. Wireless Bluetooth headphones don’t have unsightly cords, but can potentially cause problems with other devices, such as a microphone, and result in muffled sound.
• Connection: A strong network connection, preferably hard wired rather than via wi-fi is essential. 

20. Every virtual sales kickoff, even smaller ones hosted on Zoom or a similar platform, should have a skilled team behind the scenes facilitating the technology so speakers can focus on presenting. The larger and more involved the virtual sales kickoff is, the more important the production team becomes.

21. There are a lot of moving parts to putting on a virtual sales kickoff. I have included many, but not all, in this post. To keep the big picture in focus, many event planners say that there are two keys to managing all of it: Creating a checklist of things that need to get done and a timeline for when you need to do them.

The art and the science of a virtual sales kickoff

If you are new to producing virtual events, the many elements to take into account can seem like a lot to digest. However, what is most interesting is that there is no hard and fast right way or wrong way to put on a great virtual sales kickoff. In fact, it is just as much art as it is established science. 

I recommend always keeping your audience in mind as you plan your sales kickoff. What would they want? What’s best for them? And here is the ultimate test of your success: Will people become a fan of your sales kickoff and eagerly look forward to your next one?

There is a lot to consider when running a virtual sales kickoff. I hope I have provided you with some valuable background information as you think about putting together your own virtual sales kickoff. As with any business initiative, there are a wide range of factors and considerable planning that will help contribute to your success.

If you are looking for an outside speaker for your virtual sales kickoff, please reach out to me so we can discuss your event. Besides speaking, I can help you plan amazing virtual experiences, manage costs, and more. Together, we will create a world-class event that will win fans for your business. Beyond the "keynote style" part of my talk (that’s outlined below), I’ll also work with you to include elements that I discuss in this post such as Q&A, polling, chat, or fun "surprises" to keep the audience interested. 

My talk, titled "Turning Customers into Fans in Challenging Times" will talk about how the pendulum has swung too far in the direction of superficial online communications at a time when people are hungry for true human connection. In today's Covid-19 world, we all have an opportunity to use online media, especially video, to reach people and create those powerful connections that make sales and build fans.

2021 presents a great opportunity for organizations that adapt and innovate. Your virtual sales kickoff can either fuel your growth or fall flat and leave you scrambling to recover. Do not miss your chance to start 2021 off with a virtual experience that your audience will truly love.