Make Your Sales Kickoff the Party of the Year

It’s true: I once fell asleep during a sales kickoff. I didn’t mean to, but nature is bound to take over when you’re sitting through the sixth presentation in a row. 

When I came to, I made a solemn vow: When I became a sales leader one day, I’d never throw a boring sales kickoff. Today, I’m Head of Sales at Slack, and I’ve made good on that promise (or so my entire sales team tells me).

Here are my strategies for throwing a sales kickoff that captivates and energises your sales force and team for the new year. It starts and ends with a simple principle: Put yourself in your audience’s shoes, and give them something good.

What you’ll learn:

What is a sales kickoff (SKO)?
What should be included in a successful sales kickoff meeting?
How do you plan a sales kickoff agenda?
Sales kickoff tips and best practices

What is a sales kickoff (SKO)?

A sales kickoff is an event where the company’s sales team gathers together, often at the beginning of the fiscal year. It’s a chance to celebrate wins from the previous year, set goals for the coming year, and share lessons and strategies to help each other win. 

 SKOs are all about:

• Camaraderie. This is the time to deepen connections that will carry us through the rest of the year. 
• Collaboration. Team selling is more important than ever, and sales kickoffs help us sell faster and smarter when we learn more about each other’s working styles. Often a sales kickoff will include partners from other teams, like solution engineering and customer success, who are critical to the sales cycle. Building these relationships is critical to working more effectively together throughout the year.
• Excitement. Sellers begin their pitches by understanding the customer’s why. Same goes for sales kickoffs. My sales team is full of people who want to create generational wealth for their families, advance careers, help their customers, and gain freedom. So I create content that touches on those themes to get people excited. 

What should be included in a sales kickoff?

A great sales kickoff includes team-building product training, recognition, interactivity like workshops and discussions, and, yes, presentations (but not too many, please). Here’s a closer look at the key elements of a sales kickoff.

Team-building

Team-building exercises help us peel back that professional layer on the surface, and make personal connections based on rapport (“I like you”) and trust (“I feel that you have my back”). These exercises also create valuable networking opportunities, where employees and leaders from different teams can step outside their circles and connect. Here are some ideas:

• Rock, Paper, Scissors Extreme: Pair off and play Rock, Paper, Scissors. Every loser joins the Hype Team of the winner, following them around and cheering them on. In the end, there’s the final battle between the two finalists, with their massive Hype Teams behind them.
• Shark Tank Fail: Teams of two pitch their very worst business ideas to a panel of judges, and the team that makes people cringe the most is the winner.
• Flip the Tarp: Place groups of people on a large tarp, and ask them to flip it over while standing on top of it, without touching the ground.

Recognition

Weave recognition into your next annual sales kickoff meeting to celebrate wins from the previous year and create some healthy competition to outdo each other in the year ahead. Here are some examples:

• Awards: Give away awards to top performers and get creative with the categories. Some examples: Achievement Award for hitting a sales record, Leadership Award for being a great manager, Growth Award for being the most improved player, Team Morale Award for bringing great vibes, and Salesmanship Award for elevating the craft.   
• Leaderboard: Pull together data from across your sales dashboards and present a Leaderboard to show how top performers rank across sales metrics, like close rates and sales cycle length. 
• Appreciation Shower: Group into circles of six to ten people and give spontaneous shout-outs to each other. 

Interactivity

Bring in interactive elements to make your next sales kickoff meetings more engaging and give your sales teams a chance to converse. Here are some ways to do it:

• Workshops: Organise people into groups and ask them to work on solving a problem together, like ideas for launching a new product, growing the business, or selling into a new industry, region, or company type. At the end, ask a representative from each group to present on what they discussed.
• Roundtables: Encourage everyone to join in with roundtables, which are organised conversations that give everyone a chance to speak. Typically a moderator will kick it off by introducing a topic, then go around to facilitate table by table.
• Panel discussion: Feature a panel of speakers who can share diverse points of view on an important topic, and include an Q&A that encourages audience participation.

Presentations

At sales kickoffs, you’re usually launching something new. Maybe you’re launching a new product, selling into a new industry, or tweaking the sales process. Use presentations to help the team walk out with confidence to sell, and remember to frame your content with what’s in it for them. What will help them drive the business? Dig into topics like these: 

• Product announcements: When I’ve gotten stuck in my career, I’ve always broken through by bringing it back to basics. What are the products? What do they do? Use the sales kickoff to discuss product announcements that will help your sellers go to market.
• Industry trends: We owe much of our success at Slack to the fact that we speak the language of the industries we sell into. Use the sales kickoff to present on trends, risks, and opportunities in your target industries, so sellers can bring more expertise to the table when they meet with customers.
• Sales strategy: The sales kickoff often happens shortly after you create your annual sales plan and sales strategy at the end of the fiscal year. Now’s the time for sales leaders to present the top-line goals and tactics and get the sales team in lock-step to achieve them.
• Customer panel: Customer speakers tend to be the favourites at the sales kickoffs I’ve been to. It gives the sales team to hear about the product and the industry from decision-makers we sell to, and leaves time for them to ask questions.

How do you plan a sales kickoff agenda?

When you’re planning an agenda, find a comfortable venue with different areas to break out, set aside time and budget for group meals to come together and relax, and dream up surprises to thrill the audience, like an exciting keynote speaker they’d never expect. 

Here’s a sample agenda to get your juices flowing:

Day 1: 

• Breakfast and introduction. Fill up your attendees with eggs and caffeine, tell them what to expect in the coming days, and leave space for people to greet each other, shake off the nerves and the jet lag, and choose a place to sit down.
• Look back and look forward. Look back on the previous year and share lessons learned, including highlights and lowlights. Then, shift to the year ahead, announcing important changes and goals.
• Keynote speaker. Invite an exciting guest speaker, like one of your company’s most beloved executives, a customer from one of your biggest deals, or even a celebrity. For example, our sales kickoff at Salesforce once featured football legend Peyton Manning,  who discussed how to go for growth. 
• Lunch
• Rock, Paper, Scissors Extreme: Described in the team-building activities section, this high-energy game shakes off any afternoon doziness and helps people let their guards down.
• Sales strategy presentation: Make the transition from a discussion on strategy to a presentation, so sales leaders can share their vision for the year ahead.
• Roundtable discussion: Company strategy. Pick an important topic you’re wrestling with, like how to penetrate a new market, or which product line to invest in next, and invite everyone to weigh in.
• Leaderboard: End the day on a high note, sharing the top performers across the metrics you care about, and getting everyone amped up for dinner.
• Dinner

Day 2:

• Breakfast
• Product presentation: Get down to business with critical presentations sharing important announcements that will enable your sales team to be more effective.
• Customer presentation: Invite a customer speaker to share why they chose your company, what’s top of mind in their industry, and how they’d recommend you engage with similar customers in the future. 
• Industry panel discussion: Invite a few guests to share lessons that help your sellers speak in the native accent — not just the language — of your customers.
• Lunch
• Flip the tarp: Remember this one from the team-building activities section? Get the energy up by getting physical.
• Roundtable discussion: Customer segmentation. Group up, so everyone can share thoughts in facilitated conversations about the topics raised so far.
• Awards: End the day on a note of recognition, having your awards ceremony to honour your team.

Sales kickoff tips and best practices

To throw a really successful sales kickoff event, first, you’ve got to define what success looks like. At the end, ask for feedback to see how you did. It’s also important to involve the right people, and invest in seeing each other in person. Let’s take a closer look.

Set goals to define success

Just as we set sales targets, we have to set SKO targets. I communicate measurable goals in every sales kickoff meeting, including both long-term goals to set a vision, and also short-term goals to set day-to-day tactics to get there.

Here are a couple examples of goals we’ve set at previous SKOs at Slack, using the V2MOM process pioneered by Marc Benioff.

• Method: Create solutions around product that solve 
• Measure: X% increase in cross-sells
• Obstacles: Organisational structure
• Method: Create a holistic plan for customer success, products, and partners
• Measure: X% accounts have an account plan
• Obstacles: Enablement structure

Get feedback on your content to see if it resonates

It’s critical to gather data on how well your content is resonating. I send out anonymous surveys at the end of each SKO to ask people about what worked and what needs improvement. I also organise a small committee and ask them to take notes throughout on the good, bad, and the ugly, so we can meet after and debrief. 

Involve people on other terms

Broaden the audience of your SKO to include anyone who’s accountable to the customer experience. For example, at Slack SKOs, we include team members from the following teams:

• Sales (all managers)
• Sales development (all managers)
• Solution engineering (all managers)
• Customer success (select managers)
• Industries and partner team (select managers)

Meet in person if you can

My advice for throwing a virtual sales kickoff? Don’t do it. There’s no substitute for meeting in person and feeling that energy in the room. That said, sometimes a company will have no choice but to go remote with their sales kickoff. For example, you might have budget constraints or a team that’s widely distributed around the globe. If that’s you, read our complete guide for how to throw a virtual event or sales kickoff.

The Met Gala? Coachella? No. It’s your upcoming sales kickoff.

Some of my fondest moments from across my career have taken place at SKOs. This is the time to think big and go all out. Do it right, and you won’t just set yourself up for a successful year of sales. You’ll also create the kinds of memories to take with you long after the SKO is over.