5 ideas to make your Sales Kickoff more engaging and impactful using lessons from 30+ years of Sales Kickoffs

While traveling home from Datadog’s 2024 Sales Kickoff I began to reflect on how successful the event was.  Then it hit me. I’ve attended, presented at, planned, or run a total of 32 SKOs over my career.  After acknowledging my age, it made me wonder, “Which were the best and why?” Some were with small, startup tech companies of 30 people and some were companies of more than 7,000.   But what made each of them impactful and engaging came down to the same basic ingredients.  Here are my top five:

1. CHOOSE A STRONG THEME TO INSPIRE AND MOTIVATE

When planning a kickoff, take time to think about how you will bring people together and focus them on what you want from them in the new year.  Bring that to the forefront before they arrive and after they've left by carefully selecting your theme. 

Most kickoff themes I've seen are single words like elevate, accelerate, believe or breakthrough.  These are catchy and can help link your sessions and content.  However, unless they are directly connected to the primary strategy of the company, these can be forgotten not too long after the event.  Instead, consider these ideas to have greater lasting impact from your kickoff theme:

• Be strategic. Find the word or phrase that represents your company or team’s big picture strategy for that year or the years ahead.  This will stick with people and guide their behavior.  
• SKO all year long. Make it something you can operationalize after the event.  It’s tough to operationalize “Believe”, but it's easier to operationalize “One Team” through actions, behaviors, KPIs, and more.  

A well aligned theme can provide a lift in energy and focus not only at the kickoff but throughout the year.  This can motivate people leading to greater engagement and commitment to the company and the cause.  All of that will provide a lift to your business results.  One year at Splunk, we were transitioning from traditional perpetual licensing to subscription and cloud which required a new way of looking at the customer relationship - land, adopt, expand, and renew.  The theme we chose was ‘Journey’.  We were able to use that at SKO, and all year through, to educate and enable our teams on what the phases of the journey were for our customers and what we needed each team to do along the way.

2. INCLUDE PLENTY OF NETWORKING TIME

Don’t underestimate the importance of human connection.  Build in networking time with longer breaks, 30 minutes or more.  Hold more receptions in the evenings with appetizers vs. seated dinners to encourage people to mingle and network.  And be creative. There are no limits!  One year at Splunk our team created an evening reception that was set up like a trade show floor, complete with booths where each product group, supporting GTM team, corporate function (IT, HR, Finance, etc), and execs were present.  Attendees could learn about the latest from each team and ask questions all while networking and enjoying food and drink.  Databricks has been equally creative delivering networking and connection through giving back to local communities every year at SKO.  This networking helps people feel more connected to the company, their mission, and their teams.

3. LEAN IN ON RECOGNITION

Over my career I’ve seen recognition have significant value to salespeople.  For some, it’s critical.  Seeing your name on the big screen, running up to the stage to have your photo taken with the CRO and CEO, and having your peers congratulate you all night can be incredibly energizing and satisfying.  Here are a few ways to lean in further on recognition: 

• Open the aperture. In addition to having the "top" awards, consider offering some for people who live your culture and values and awards for non-sales team members who go above and beyond to help sales win.  I’m not saying give everyone an award.  But you can benefit from expanding to reward not only the numbers delivered but 'how' people got to the numbers and who contributed.
• The Big Intro. When you give the award tell a short story about each winner before calling them up.  Build it up like you’re introducing a guest speaker.  Prime the audience to give their biggest reaction and cheer for that person.  And give them a physical award, plaque, certificate, or trophy.  That and taking pictures on stage with the senior executives will make the winning more impactful.
• Celebrate in style. Make your awards ceremony a big deal; a formal dinner can be impactful.  Add formal dress, a red carpet, a photographer, and live music to spice it up.  

These moments last for a long time in people’s memories, build loyalty, and motivate others to work harder in the new year. Often these nights are played back on social networks, like LinkedIn, which will reflect well on your organizational culture to the world.  

4. ENGAGE THE ENTIRE GLOBAL ECOSYSTEM 

Invite everyone in the GTM ecosystem that surrounds your sellers to your kickoff - marketing, channels, customer success, strategy, deal desk, operations, etc.  Organize your event to ensure full representation of that ecosystem in main-stage presentations as well as breakout sessions.  Get their participation and mention them in success stories, awards, and other kickoff content.   Want to make your event even more ecosystem-focused?  Here are a few ideas:

• Change it up. Consider changing the name and call it a Go-To-Market Kickoff.  After all, we all know that it takes much more than Sales to have success selling a product.
• Think globally. If you are a global company, highlight your global regions on stage.  Regional videos are a great way to do this.  Task each major region - Americas, EMEA, APJ, LATAM, etc - with building a 2-minute video showcasing their team, their region, how they work together, and how they play together, and encourage them to make it fun adding music and humor.  The regional teams at Datadog outdid themselves with this year’s videos.  One region included a guest appearance by one of the executives that caused the room to erupt with laughter.  

The energy and pride that come from these types of videos can last a long time and help the audience at your kickoff to feel more like one team.  You will also find that it’s great to open sessions with these to warm the crowd up and it’s equally good to use them to close out a section of content, bringing more energy to the crowd just before a networking break.

5.  ALIGN YOUR SUCCESS STORIES AND WINS TO YOUR FOCUS AREAS

Sales teams love to hear success stories.  They want to know how their peers have overcome obstacles from competition, pricing, proof of concepts, access to executives and more.  They want to learn.  Often, though, SKOs feature only the biggest deals.  This makes it very hard for sales teams in the audience to consider applying lessons from a $20M transaction to their $100k opportunity.  It’s also difficult for a sales team in Tokyo to apply the learnings from a win in New York.  Here are a few ideas to help make these more impactful:

• Right size your success stories.  Highlight wins of different sizes.  This allows people to see what is needed to succeed at each level.  It should be obvious that the challenges to overcome on a $20M sale are different than a $200k or $20k one.  
• Act locally. Feature wins from each major geography.  Not only is it good for your culture to feature people from across the globe, it will ensure that every rep walks away with something they can take and apply immediately to succeed in the new year in their unique region.
• Choose wisely. Consider choosing the success stories carefully so you can align them to your theme or to the asks you are making of people.  For example, if your theme for kickoff is “One Team” then choose success stories where the entire team presents what they did.  Or, if you’re doubling down on building business cases this year, highlight success stories where the business case played a big role in winning.  Be careful who you feature on stage, though.  You might have a seller who doesn’t follow the process or does things more "artistically" which can be difficult for others to repeat or goes against what you want people to do.

CLOSING

While every company is different - size, maturity, product, culture, and more - we're all humans and humans love to connect with others, to be inspired, and to help and be helped.  If you’re about to execute your kickoff program, it’s not too late to add some of these elements to boost the overall engagement and the resulting business impact.  And if you’re starting the planning for the next kickoff, as we are, use these key ingredients as anchors to make a meaningful, memorable, and impactful kickoff reaping the benefits of it throughout the entire year.  

Doug May is a seasoned salesperson, sales leader, and GTM executive with more than 25 years of experience in building and leading teams helping companies to accelerate revenue growth and scale.  Over the last 13 years he has held roles as the VP of Global Field Specialization at Splunk (NASDAQ: SPLK), VP of Global Value Acceleration at Databricks, and he currently is the Chief of Staff to the CRO at Datadog (NASDAQ: DDOG).