Strategies for a Successful SKO for 2024

Sales kickoff (SKO) sets the stage for shaping the sales trajectory in the upcoming year. It’s also likely the largest single investment you’ll make in your sales team for the next 12 months. I conducted some research that showed more than 60% of organizations allocate a minimum of $1k per person for their sales kickoff — with nearly 30% spending at least $2k per person. 

Given this substantial commitment, the onus falls on sales leaders to ensure SKO has an impact on performance. And as your kickoff date looms, it’s pivotal to strategize effectively to build an engaging event that captivates, empowers, and inspires your salesforce.

Pre-SKO: Be Proactive to Maximize Your Investment

The purpose of an SKO is to catalyze measurable outcomes within the sales organization. And to do so, you’ve got to start planning well in advance. 

Establish Where You Are

Use your own data to kickstart SKO prep. Evaluate team and individual reports to set a baseline. 

Sales cycle. Monitor whether the average sales cycle has increased or decreased over time. Identify trends among certain reps or teams, and analyze what they’re doing differently. 

Stage conversion data. Pinpoint where in the funnel you’re losing the largest number of prospects as well as areas of success. Strategize methods to increase conversions throughout your funnel.  Look at what you measure today like lead to opp conversion rate, opp to close win rate, and other friction points in your sales funnel.

Team benchmarks and performance. Review reps’ performance against set goals, as well as year-over-year changes. Identify challenges encountered at specific stages and what enablement is needed to fill in gaps. 

Determine Where You Want to Be

Based on your sales data, set clear goals for the event — goals that link directly to tangible metrics, like:

• Percentage of reps making quota
• Customer retention
• Number of opportunities generated
• Win rate

Incorporate qualitative metrics as well, including cultural and business changes (e.g., higher employee satisfaction) and what you want reps to know after SKO. This creates clarity and serves as concrete indicators of success not just immediately following the event, but throughout the year ahead. 

Get Everyone in the Same Boat — Rowing in the Same Direction

Mission-critical when building out your agenda and content is involving various stakeholders. Ask a top-performing rep and a rep with average performance (not necessarily telling them who’s who!) for input. Let them lay it all out, from challenges and needs to preferences and the day-to-day practices they’ve found success with. These can inform so much of your approach — not just the content, but also its format (more on that later).  

Bring in colleagues from external departments to give their two cents. 

• Marketing leaders can provide insights into what products, campaigns, and messaging have had the most success, as well as how your teams can collaborate better. 
• Partners bring a broader industry perspective. 
• Ask your CEO for initial input and get their final go-ahead on the SKO agenda to ensure the goals, values, and vision align with those of the overall organization.  

During the SKO: Engage, Engage, Engage

Executing a successful kickoff event hinges on an engaging and purpose-driven agenda. Pre-work offers an opportunity to deliver information about a new product, updated features, or a new tool or methodology you’re integrating for the team. This way, time during the SKO can be spent more valuably, answering any questions and digging further into use cases. You can even do a certification or have reps present on pre-work topics during kickoff.

Start With the Good

Get the SKO rolling on a high note by opening with an awards segment. Acknowledge and celebrate the wins and successes of the team to foster positivity that can resonate throughout the entire event. These also establish a sense of camaraderie and appreciation, demonstrating the value of individual and collective achievements while creating a lighter, celebratory atmosphere that primes everyone for the productive sessions ahead.

Switch Things Up

To maintain attention and participation (especially over two- or three-day events), switch up the format of different sessions. Rather than falling into “death by slides,” add some of these into the mix:

• Pre-recorded interviews and hype videos showcasing customers, team members, and other employees talking about the previous year’s successes and excitement for what’s to come.
• Customer panels, where invited customers tell sellers about their experience throughout the sales process and beyond — including their prior status quo, why they decided to buy, and how they measure success.
• Breakout discussions for smaller groups to discuss challenges, best practices, and more to present back to the larger group.
• Contests that add some fun and friendly competition. Host a “Jeopardy”-style quiz game or a Shark Tank pitching contest where reps or teams rank each other on their sales skills.

Share Highs and Lows

Use a portion of your SKO to go through business cases of your solutions to impart practical insights and invaluable lessons. Selling on features and price won’t close deals; reps need to tell a consistent value story throughout the buyer journey.

SKO is also a platform to showcase both stories of success and instances where reps or teams came up short. Get relevant parties involved to tell the story — the more detail, the better — including:

• How the meeting was secured
• Content delivered to the buyer group
• Pain points and business issues
• Interactions throughout the process
• Metrics of success

Post-SKO: Combat the Forgetting Curve

You may leave the kickoff thinking, “that was fun,” but did it actually change behavior? You’re investing a lot of time and money into the event and want to make sure the learnings stick. It’s impossible to reiterate the mission, vision, updates, and content too often! 

It’s no surprise sellers forget details over time — you dump a bunch of new information for hours, go out for dinner and do it all again the next day. Sales leaders must commit to reinforce SKO content throughout the year to move the business where you want it to be. 

This reinforcement can take many forms for reps:

• Certifications
• Video role plays
• Self-evaluations for real calls
• Teaching a specific module to the rest of the team
• Cross-team pollination and knowledge sharing

Make sure SKO decks, recordings, and videos are readily available. If you don’t have one already, create a content hub to store these materials, as well as other sales and marketing content. Reps can revisit as needed, without wasting time finding the most up-to-date and relevant information. 

Finally, remember that your job has only just begun. The purpose of training in an SKO is to teach reps skills — coaching is what helps them master them. Regularly meet one-on-one with members of your team to evaluate recorded calls, talk through deals, and guide them toward solutions. Give them homework in between (e.g., a call scorecard based on questions asked, communication style, and other criteria) to inform conversations.

Game On!

Are you ready for kickoff? Your SKO is more than a moment in time; it’s an investment in the future success of your sales organization. Start planning ASAP, keep the content fresh and engaging, and promote ongoing learning to fuel continuous improvement throughout the year. Get the most out of your time and budget and solidify the event as a launchpad for long-term growth.

Learn how Mediafly can help you combat the forgetting curve and coach your reps to revenue success all year long here.