Planning and Executing a Successful Sales Kickoff

It’s time to plan the annual sales kickoff! Are you excited — or groaning to yourself? The truth is that a sales kickoff is often nothing more than a hype meeting, but it can be so much more.

An effective kickoff communicates your go-to-market messaging for the next year, celebrates previous wins, sets your sales team up for success, and helps reinforce a positive sales culture. It’s more than a party — it’s a party with a purpose.

As a sales enablement professional, you play a key role in the success of your sales team. The sales kickoff (SKO) is a great opportunity to align sales with other departments, communicate vision, and inspire everyone. 

Here’s how to plan and execute a great kickoff!

What separates a good sales kickoff from a bad one?

There are ways to kill the buzz at your sales kickoff meeting immediately or to start the year off on the wrong foot. Here are some mistakes to avoid as you plan your annual meeting.

Don’t lead with bad news

Are you rolling out higher goals, a new and controversial tracking system, or anything else that would immediately dampen the mood in the room? If so, don’t start the event with that news.

Instead, have a plan for rolling out tough information. For example, you might wait until most of the way through the first day’s presentations or share the difficult stuff before announcing a great bonus or releasing the group to a much-anticipated event. 

If you plan to have a speaker after making this kind of announcement, work with them in advance, so they know what to expect and can tailor their message to embrace change positively.

Skip the boring trainers

When we say “skip the boring trainers,” we mean skip long-form training altogether. Instead, roll out training using an all-in-one training platform like WorkRamp so sales reps can be engaged as they learn.

Internal or external, trainers are often equipped with long PowerPoint presentations and a monotonous drone. On the other hand, sales reps are often high-energy — especially at a kickoff event!

Use your SKO to communicate strategy, celebrate the previous year, and encourage your team. Keep training short and sweet, and your sales reps will be much more engaged and ready to succeed.

Make sure you include interaction and networking

One of the things all professionals love is the opportunity to “talk shop” in an informal setting with coworkers. It can be challenging to create this in daily life, so make sure your sales kickoff meeting includes plenty of time for hanging out.

If you want to hit it out of the park, purposely include speakers and workshops based on group interaction and connection. This gives colleagues a chance to work together in a new environment in addition to partying together. 

Of course, you want to stay far away from the corny, cliche team-building. But when you build real, useful interaction into your event, you’ll not only encourage relationships — you’ll also make the entire event more memorable, which will help your reps remember your message.

What to Include in Your Sales Kickoff Event

One of the things that’s so challenging about creating a sales kickoff is that there are so many choices! You might end up getting overwhelmed with the possibilities and just reverting to “what we’ve done before.” 

To avoid the rut, start by scheduling the necessities and then add fun and interaction. Here are some ideas for what to include in your SKO.

Inspiration

People need encouragement and motivation regularly, and a sales kickoff meeting is the perfect time to lift everyone at once with the right keynote speaker. Whether the speaker is internal or external, it should be someone with positive energy who has experienced great success. 

A keynote is a perfect spot for your headliner, the person the sales reps will be excited to see. For example, you might be able to hire a successful celebrity or athlete to encourage your team. Getting everyone motivated makes the rest of the event go much more smoothly.

Short focus sessions

Once you’ve encouraged everyone with a kickoff speaker, you’ll want to use short sessions to break up the rest of the content. People love super-short sessions like TED Talks, which share information but aren’t overwhelming.

You can also host group competitions, practice overcoming objections, talk about how to implement the new go-to-market message, and more. In a short time, your sales reps can leave knowing they’ve learned something they can apply to their work.

Decide how you want to break up your sessions throughout the day or a multi-day event. For example, will each day have a theme? Or will you present a mix of information throughout?

One excellent way to present new information is through an all-in-one learning system like WorkRamp. For example, Algolia uses WorkRamp to optimize both push and pull learning and embrace video training and virtual events. You can use WorkRamp to facilitate a learning session that’s short, fun, and engaging as part of your sales kickoff.

Have customers share

One of the best things you can do to galvanize your sales reps is to show them that they are making a difference. It’s wonderful to hear that from you, but why not have actual customers come in and talk about their results with your product or service?

These presentations are fun for sales reps to listen to and can give them a lot of great material for future sales calls. Best of all, the team gets kudos from the most important audience — the customer.

Talk about how changes improve the ability to sell

Most SKOs involve announcements about new features for your product or service. Instead of simply rattling these changes off, talk specifically about why the changes were made and how that improves the reps’ ability to make a sale. 

For example, was a change made due to customer feedback? Because the sales leaders saw a trend in lost sales? When you showcase the features in context, your sales reps will be more excited and bought to the changes you’re making.

Showcase major sales wins

There’s nothing that fires up sales reps like getting to talk about their victories. Take advantage of your sales kickoff meetings to feature your top sales reps and interview them about how they did so well in the past year.

Not only does this allow top performers to show off their knowledge, but it’s also a very effective way to teach techniques. We’re all more willing to listen to successful peers than people we perceive to be in authority over us.

As you choose who to have up on stage, focus on the sales reps you want others to emulate. If there are reps you don’t want to bring up in person, you can simply give them a shoutout for their results.

Pump your team up about next year’s goals

As you celebrate your team’s previous successes, you also want the team to know what success looks like next year. You’ll want to work on how to showcase any changes in quota or other metrics as a positive move forward.

You can talk about both short-term and long-term goals so that sales reps know where the company is headed overall and what steps they can take to get there.

How to Organize a Sales Kickoff

Now that you know the elements to include, how should you organize your SKO? There’s no single right answer to this question, but thinking about your priorities and timeframe can help.

Set the stage

The first things to consider are your SKO team and theme. 

First, who is going to be working with you on the event? If it’s just one or two people, you’ll need to limit your expectations on the size and scope of your kickoff event. On the other hand, if you have a strong team, you can pull out all the stops.

The theme is usually linked to the overall “big change” you want to make next year. For example, it could be focused on improving customer experience, or you could center the sales kickoff on your new go-to-market message.

Having the right theme is a great way to organize your events and content and can help your sales team align with other departments in the company. Studies show the importance of aligning sales and marketing: misalignment causes companies to lose millions of dollars due to wasted efforts and lost productivity, while sales and marketing alignment can increase closed deals by 67%.

Include the right people

While a sales kickoff is usually focused on the sales team, other departments can also add a lot of value. Since you have your whole team in one place, this could be a great opportunity for other department leaders to talk about how they support sales and how they benefit from the work of the sales team.

Your organization shouldn’t operate in silos, and the sales enablement team is part of helping everyone integrate. Just ensure that the people you choose to have on stage are positive, excited, and understand how to tie into the theme. 

You can also think about other keynote speakers you’d like to invite. They can be either internal or external. Don’t be shy about vetting your speakers before you commit — getting references and reviews is good business.

Include a mix of activities

Sales reps generally expect an SKO to be energetic and fun while providing insight into how to do their work more effectively. The best way to meet that expectation is to provide a mix of activities.

For example, you might rotate between celebration, new updates, interaction, motivation, customer insight, and education. By keeping things varied, you’ll create more interest while still getting the core message across to your team.

Going virtual? How to have a successful virtual SKO

While in-person events are returning in force, many teams cannot have a local, physical sales kickoff. Maybe your team is spread across states or even countries as remote workers, or perhaps your budget and timeframes don’t allow for an in-person event.

If you want to have a successful virtual sales kickoff, there are several things to keep in mind. First, think outside the box. Your virtual event will look different from a typical in-person one, but that can be an advantage! For example, using multiple half-days for your SKO can allow your team to work part of the day and avoid the stressful work pileup that comes with being out of the office for several days.

Secondly, help your speakers prepare for virtual keynote presentations. They won’t be able to see the audience as well, so let them know your sales team’s general interests and demographics. Also, help them work their presentations into the theme you’ve chosen. 

Finally, test your technology well in advance. While you can’t guarantee everything will go perfectly, testing will allow you to discover and solve common problems that might come up. Designate a technical support person to standby on the day(s) of your sales kickoff in case anything goes wrong. 

Set your team up for success with a great sales kickoff

There’s nothing like a great sales kickoff meeting to galvanize your team, celebrate last year’s successes, and help everyone see the vision for the year ahead.

When you incorporate WorkRamp, you can ensure that your learning sessions are engaging and fun for everyone. We’d love to showcase how WorkRamp can help your sales kickoff be a tremendous success. Contact us today for a demonstration!